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This post has been a long time coming. Life is a lot busier now than it was when I wrote my earlier blogs, so rather than waiting for the “perfect” time, I wanted to get this published before our next adventure: The Lofoten Traverse in Norway.

To make that happen, I borrowed the structure from my Tour du Mont Blanc blog and built from there. I also leaned on AI more than I have in the past to help organize and shape the story. Planning this trip was significantly more complex, and I simply don’t have the same amount of free time I did when I wrote my earlier adventures.

That said, every experience, opinion, and lesson is my own. I’ve read through this post more times than I can count, editing and fact-checking it until I felt it accurately reflected the journey. AI helped me write more efficiently, but the story is still mine.

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How the Trip Came Together

“Hey Conor, want to come with us on the Torres del Paine?”

At the time, I was pronouncing “Paine” like the English word pain, so all Conor heard was,

“Do you want to come with us on the Tour of Pain?”

As you could imagine, he said no the first time 😅

At that point, I believe it was just Dillon and me who had fully committed to the trip. Originally, we were planning to visit Patagonia during the Southern Hemisphere’s fall. Looking at photos online, it was hard not to be drawn toward that season. The glacier-blue lakes contrasted against red, orange, and yellow foliage looked almost unreal.

The problem was that I hadn’t considered Dan’s schedule before I started inviting people.

Dan is a teacher and understandably didn’t want to take additional days off this early in his career. It wasn’t that his school wouldn’t necessarily allow it. Teachers already receive generous breaks throughout the year, and from his perspective, asking for even more time off when he already gets so much didn’t feel right.

There was another complication as well. Long before I suggested this trip, Dan had already promised a close friend that if they ever had the chance to visit Patagonia together, he’d go.

So when I first asked him, the answer was no. Between the timing and the commitment he’d already made, it simply wasn’t the right trip for him.

At the time, I figured that was the end of it.

Instead of accepting that, though, I started looking at the calendar a little differently.

If we shifted the trip from Patagonia’s fall to its summer, the dates suddenly lined up with his winter break. The more I researched it, the more it seemed like the better option anyway. Patagonia’s fall is beautiful, but it also comes with a much greater likelihood of carrying true winter gear. During the Southern Hemisphere’s summer, we’d still have to prepare for Patagonia’s famously unpredictable weather, but the overall equipment list would be much more manageable.

That solved one problem.

It introduced another.

Christmas is important to everyone who came on this trip. None of us wanted to spend Christmas in an airport or halfway around the world. We all wanted to be home with our families.

At the same time, Dan still needed to be back before his students returned from winter break.

That left an incredibly narrow window.

The trip had to begin after Christmas, end before school resumed, and still leave enough time to justify flying all the way to Patagonia.

Eventually, after more calendar juggling than I’d like to admit, everything lined up.

The school schedule was no longer an obstacle.

By then, it had also become increasingly clear that Dan’s other Patagonia trip wasn’t going to materialize anytime soon. His promise to his friend was now the only thing preventing him from committing, so he went from a firm “no” to a genuine “maybe.”

That was enough for me.

Then I realized something I hadn’t fully considered.

The O Circuit isn’t a trail where you simply decide each morning how far you feel like hiking. Campsites must be reserved months in advance, and the park expects hikers to move through them at fairly strict intervals. Those campsite reservations essentially determine your itinerary.

At first, I didn’t think there was a solution.

If Dan couldn’t finish the trek before school resumed, then he simply couldn’t come.

That was the reality I had accepted.

Then, while studying the reservation systems more closely, I realized something that completely changed the problem.

The two companies managing the park’s campsites didn’t communicate with one another.

That tiny detail became the key to the entire trip.

For the first time, shortening the itinerary became possible.

But almost immediately, another problem appeared.

The people I invited all had different levels of backpacking experience. Dan is more than capable of comfortably hiking 20-mile days, but I couldn’t redesign the entire trip around the strongest hiker in the group. What made the original itinerary enjoyable was that it challenged everyone without pushing anyone beyond what they had signed up for.

That’s when I did something I’d never done before.

I created two separate itineraries.

The main group would hike the O Circuit exactly as I had originally planned it.

Dan would hike the same itinerary alongside us through the remote northern half of the circuit. Then, after Grey Glacier, our routes would finally split. Using the gap created by the two completely separate reservation systems, Dan would combine our final four hiking days into just two, while the rest of us continued at the original pace.

Shortly after I proved he could complete the trip using the second itinerary I had designed to get him back before school resumed, and once it became clear that the Patagonia trip he had promised his friend wasn’t going to happen anytime soon, Dan bought his plane ticket.

Looking back, I’m oddly proud of this part of the planning. It wasn’t just about finding campsites—it was about solving a puzzle where every solution seemed to create another constraint.

• We wanted to spend Christmas with our families.
• Dan needed to be back before school resumed.
• The park dictated where hikers could camp each night.
• The itinerary had to work for hikers with different experience levels.

Realizing the two reservation companies didn’t communicate wasn’t just a neat discovery.

It was the piece that made the entire trip possible.

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Designing Two Trips Instead of One

My original itinerary wasn’t something I created from scratch. It was based on several published itineraries that followed the park’s required campsite progression. I liked the pace because it felt like a proper backpacking trip while still being approachable enough that I could invite friends with different levels of backpacking experience. It was long enough to feel like an adventure, yet relaxed enough that we’d have time to enjoy camp, take photos, and simply appreciate being in Patagonia.

Creating Dan’s itinerary, however, wasn’t as simple as deleting a couple of campsites.

The challenge wasn’t the hiking—it was the reservation system.

To hike the northern portion of the O Circuit managed by Vértice Patagonia, you don’t simply reserve the campsites you want. You choose a start date, and from that point the reservation system expects you to purchase every campsite in the required progression. That progression exists largely because of John Gardner Pass, the most remote and demanding section of the circuit. It naturally spaces hikers out and discourages people from attempting excessive mileage before or immediately after the pass.

Fortunately, the way the reservation systems were structured meant we didn’t have to split up right away. We were able to experience more than half of the entire O Circuit together. Up through Grey Glacier—and technically our reservation at Paine Grande, the final campsite managed by Vértice Patagonia—our itineraries were completely identical.

That’s where the opportunity appeared.

Although Dan still had to reserve and pay for Paine Grande to satisfy Vértice’s required booking progression, he didn’t actually have to spend the night there because what came next was no longer dictated by the previous campsite. From Paine Grande onward, the campsites are managed by Las Torres Patagonia, whose reservation system doesn’t require hikers to reserve campsites as part of a fixed progression. Instead, each campsite can be booked individually.

That subtle difference was all the flexibility we needed. It meant Dan didn’t have to leave the group until he absolutely had to. We still got to cross John Gardner Pass together, experience Grey Glacier together, sharing most of the adventure before our itineraries finally split. From there, Dan combined what would have been our final four hiking days into just two before returning to Puerto Natales in time to fly home before school resumed.

Date	Main Group	Daniel
Dec. 28–29	Travel together and stay in Puerto Natales	Same
Dec. 30	Park Entrance → Dickson (19.6 mi)	Same
Dec. 31	Dickson → Los Perros (7.03 mi)	Same
Jan. 1	Los Perros → Grey (8.71 mi)	Same
Jan. 2	Grey → Paine Grande (6.72 mi)	Grey → Los Cuernos (~21 mi)
Jan. 3	Paine Grande → Los Cuernos (14.7 mi)	Los Cuernos → Finish Trek (~16.7 mi)
Jan. 4	Los Cuernos → Chileno (7.73 mi)	Half Day in Puerto Natales & Flight Back Home
Jan. 5	Chileno Base → Finish Trek (8.81 mi)	Flight Home
Jan. 6	Continue exploring Chile	Back in the classroom

Daniel’s itinerary isn’t something I’d recommend to the average backpacker. It worked because Dan is a seasoned long-distance hiker. He knows exactly what kind of mileage he can comfortably cover, and more importantly, he knows how his body responds after several consecutive days on the trail.

Most people would be miserable trying to replicate it, but to better illustrate just how different the two itineraries became, I’ve included the maps side by side below to complement the comparison table above.

Why I Was Willing to Build an Entire Second Itinerary

Some people might think it’s strange to reorganize an international trip around one person.

Honestly…

I’d do it again.

In fact, I already have.

After seeing how well this worked, I ended up doing something similar for our Lofoten Traverse in Norway, creating a modified itinerary so another friend could join us despite having different scheduling constraints.

I’ve come to think of it as another tool in the toolbox rather than an exception.

Dan genuinely makes every trip better.

He’s one of those people who always seems to have another story, another random piece of history, or another observation that somehow makes the day more entertaining because of the way he looks at the world. More importantly, he commits. He never complains about difficult miles and somehow manages to make suffering—usually mine—seem funny.

Backpacking trips like these are never just about the scenery. They’re about the people you experience them with.

So if spending a few extra weeks designing another itinerary meant one of my closer friends could experience one of the world’s greatest backpacking trips…

That seemed like a pretty easy decision.

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Planning the Trip

Selecting the Route

Torres del Paine has two primary multiday trekking routes: the W Trek and the O Circuit.

The W Trek is the more common option. It covers the park’s most famous southern attractions and can generally be completed in several days mapped for approximately 38 miles, although the total distance varies depending on side trips, accommodations, and how the route is measured.

The FarOut guide begins its mileage at Refugio Grey, but most hikers either start at Central (the same entrance where we began the O Circuit) or take the ferry across Lake Pehoé to Paine Grande. Hikers starting from Paine Grande hike to Grey Glacier before either returning to Paine Grande or continuing east along the W. Starting directly at Grey is possible via an additional boat transfer across Lago Grey, but it is a much less common way to begin the trek.

The O Circuit includes the entire W but continues around the quieter northern side of the Paine Massif. Our planned route was approximately 75 miles mapped via GaiaGPS, though many published estimates place the complete circuit closer to 80 miles when all major branches are included.

The most important difference was not simply distance.

The W passes through the busiest part of the park. The O includes more remote terrain, fewer hikers, and the approach to John Gardner Pass. From the pass, hikers descend toward the enormous Grey Glacier and the Southern Patagonian Ice Field.

Which Route Should You Choose?

Choose the W Trek when:

• You have limited vacation time.
• You primarily want to see the park’s most recognizable attractions.
• You are comfortable with a busier trail.
• You prefer a shorter trek.

Choose the O Circuit when:

• You want a longer backpacking trip.
• You want a simpler stop and start point (same location).
• You want to experience the quieter northern side of the park.
• You want to cross John Gardner Pass and approach Grey Glacier from above.
• You are prepared for stricter campsite sequencing and trail schedules.

Since our group consisted of experienced backpackers, the 38-mile W Trek didn’t feel substantial enough to justify traveling all the way to Patagonia. The O Circuit felt like the more fitting choice. We actually settled on the O Circuit before working through everyone’s availability, but as a group we felt that if we were making the journey all the way to Patagonia, we wanted to experience the park in its entirety.

Committed Route (Maps)

Date	Main Group	Dan’s Route	Notes
Monday, December 30	19.6 mi 🗺️Map	19.6 mi 🗺️Map	Welcome Center to Dickson
Tuesday, December 31	7.0 mi 🗺️Map	7.0 mi 🗺️Map	Dickson to Los Perros
Wednesday, January 1	8.7 mi 🗺️Map	8.7 mi 🗺️Map	Grey to Paine Grande
Thursday, January 2	6.7 mi 🗺️Map	21.0 mi 🗺️Map	Main: Grey to Paine Grande Dan: Grey to Los Cuernos
Friday, January 3	14.7 mi 🗺️Map	16.7 mi 🗺️Map	Main: Paine Grande to Los Cuernos Dan: Los Cuernos to Welcome Center
Saturday, January 4	7.7 mi 🗺️Map	—	Los Cuernos to Chileno
Sunday, January 5	8.8 mi 🗺️Map	—	Refugio Chileno to Welcome Center

Note: If you commit to hiking the O Circuit the way it’s traditionally intended, the only real difference between your itinerary and the main group set of maps is the first day. We skipped Serón and hiked all the way to Dickson (19.6 miles). Most hikers instead spend the first night at Serón, making it an 8.2-mile first day followed by an 11.4-mile hike to Dickson the next morning. Other than that, the main group maps should closely match the standard O Circuit itinerary.

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Understanding the Two Campsite Operators

One of the most confusing aspects of planning Torres del Paine was that the campsites were divided between two private operators.

The operators maintained separate websites, separate inventory, separate payment systems, and separate customer-service teams. Successfully reserving one half of the circuit did not guarantee that the other half would be available.

This created a stressful booking problem: you could reserve several nights with one operator and then discover that a critical campsite controlled by the other operator was unavailable.

Without every required reservation, you could not complete the circuit.

Looking back, after everything I’ve detailed below—the separate reservation systems, hidden accommodation costs, technical issues, campsite progression rules, and the amount of coordination required—I honestly think most people would be better off paying someone to organize it for them.

Normally, I’m the type of person who enjoys planning trips myself, but Torres del Paine is one of the few destinations where I’d seriously consider outsourcing the logistics. By the time you’ve pieced together both reservation systems, transportation, accommodations, and park requirements, the planning can become a significant project in its own right.

There are several companies that specialize in self-guided Torres del Paine itineraries, handling campsite reservations and much of the logistical coordination while still allowing you to hike independently. Two of the more commonly referenced services I came across during my planning were Torres Hike and Booking Patagonia Travel.

If you’re someone who enjoys solving logistical puzzles, planning it yourself can certainly be rewarding. But if your goal is simply to experience one of the world’s greatest backpacking trips with as little stress as possible, paying a third-party planner may actually save both time and frustration—and after going through the process myself, I can completely understand why so many people choose that route.

Vértice Patagonia

Vértice Patagonia controlled the northern and western side of our route, including locations such as:

• Dickson
• Los Perros
• Grey
• Paine Grande

Vértice had the more reasonable prices, but the northern O Circuit came with strict rules governing the direction and sequence in which hikers moved through its campsites.

The reasonable and available camping rates of Vértice Patagonia

The O Circuit must be traveled counterclockwise. Hikers generally have to stop at the designated northern campsites in sequence. This is partly a reservation policy and partly a safety system. The route includes controlled departure times and trail-closing times intended to prevent hikers from beginning long, exposed sections too late in the day.

For an ordinary backpacker, this structure is probably beneficial. It keeps daily distances reasonable and limits the possibility of someone attempting John Gardner Pass too late.

As mentioned earlier for someone creating an accelerated itinerary, it is an obstacle.

The only realistic way to skip certain reservations within a single operator’s system appeared to be creating multiple bookings with separate starting dates. Depending on the arrangement, that could mean paying twice—or potentially three times—for campsites that would never be used.

The point was not to avoid paying. The problem was that the reservation system did not appear designed to accommodate an experienced hiker completing longer-than-standard days.

The Initial Vértice Reservation Release

When the campsites were initially released, the website was barely functional.

Important pages did not load correctly, navigation paths were incomplete, and the process had clearly not been fully quality-assured. To reach portions of the reservation flow, I had to inspect and temporarily modify elements in the page’s source code.

Thankfully, my professional experience includes front-end and back-end software testing. I can usually identify whether a page is truly unavailable or whether the necessary component exists but is being hidden, disabled, or incorrectly connected.

Using that experience, I managed to access the reservation process and secure our campsites during the initial release.

Shortly afterward, the company closed all access to booking. Fortunately, they honored the reservations I had already made.

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Las Torres Patagonia

Las Torres Patagonia controlled much of the southern and eastern side of the park, including sites such as:

• Serón
• Central
• Chileno
• Cuernos

Its route rules were somewhat looser because these properties were located near the park entrance and along portions used by both O and W hikers traveling in different configurations.

The prices, however, were horrendous:

Basic campsites appeared to be advertised at reasonable prices, but those options were never actually available when I attempted to reserve them. The company repeatedly explained that portions of its website were still under construction or experiencing technical difficulties. However, from my perspective, because those campsites remained unavailable even up until a week before our departure, those explanations became difficult to believe. My impression was that the listings may have existed primarily to satisfy a requirement to offer lower-cost camping, while in practice making those sites effectively impossible to reserve. I can’t say for certain that was the case, but that’s how the experience felt as a customer.

Two Email exchanges concerning unavailable basic campsites

The pressure was real. You cannot simply arrive at Torres del Paine and assume you will be allowed to hike the circuit. You need reservations that correspond with the correct dates and progression through the route.

Rather than risk losing the entire trip while waiting for the basic campsite inventory to appear, I reserved the expensive suspended-tent options. Thankfully, only two our our stays needed this expensive accommodation.

The suspended tents cost $165 per person, compared with something closer to $10 for an ordinary campsite—though those lower-cost sites, as mentioned earlier, never actually appeared to be available.

To me, however, it felt like an injustice. Perhaps that is simply how I am wired after growing up with two lawyers as parents. It was difficult to accept that the least expensive option was supposedly available while being functionally impossible to purchase.

The Single-Occupancy Surprise

Another lesson from this trip was not to set firm price expectations until every reservation had been completed.

One surprise came from Las Torres Patagonia’s single occupancy supplement. Several of their accommodations are priced assuming two people will share the same reserved lodging. If only one person occupies it, an additional surcharge is applied. The policy affected everything from the lower-cost campsites that, as mentioned earlier, never actually seemed to be available, to the pre-pitched premium tents we ultimately reserved. The biggest surprise, however, was discovering that it also applied to the mountain cabins, increasing the price from the advertised $280 for a double-occupancy cabin to $520 when reserved for a single occupant.

My advice is to estimate accommodation costs on the high side until every reservation has been finalized. It’s much better to surprise everyone by coming in under budget than to keep announcing that the price has increased.

Ironically, when I finally told my friends that I had underestimated the cost via a misunderstanding and presented them with the actual total, the reaction was mostly a collective shrug. I sometimes forget that the people I backpack with are not only financially responsible, but also well into their careers.

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Flight Planning

Choosing the Arrival Airport

This trip gave me my first real lesson in why researching airports and appropriate international layovers matters.

Before this experience, I generally assumed that a flight itinerary offered by an airline or booking platform was reasonable simply because it was available for purchase.

That assumption was incorrect.

Since this trip, I research:

• Whether bags must be collected and rechecked during a connection
• Whether immigration occurs at the connecting airport or final destination
• Whether terminals are connected airside
• Whether the airport is known for long immigration lines
• Whether the airline protects the connection
• Whether the published minimum connection time is realistic
• Whether an overnight delay would leave us stranded without easy accommodations
• Whether a transit visa or entry requirement applies

This lesson now affects how I plan every major trip.

For example, when I later traveled to Bali, I chose to fly west rather than east so I could travel with Singapore Airlines and connect through Singapore. The itinerary was not selected solely by looking for the shortest or cheapest option. The airline, airport, connection process, and overall travel experience mattered.

Torres del Paine was the trip that taught me to think this way.

Puerto Natales Versus Punta Arenas

When possible, fly into Puerto Natales.

Puerto Natales is the closest practical city for accessing Torres del Paine. It is where most trekkers stay before entering the park, purchase supplies, collect fuel, and board the morning buses.

Flying into Punta Arenas may be less expensive or offer more flight options, but it adds a substantial overland transfer to Puerto Natales. Depending on schedules and connections, this can consume much of a day especially if your time is more important than the monetary value.

Flying into Puerto Natales is generally more expensive, but it simplifies the trip considerably.

El Calafate, Argentina, is another theoretical option. However, that creates an international border crossing before reaching the trail. It might work smoothly, but when you are coordinating several hikers, campsite reservations, bus departures, and limited vacation time, the simplest option is usually the best one.

Our Flight Route

There didn’t seem to be a quicker way to reach Torres del Paine. Because of how remote Patagonia is, every itinerary we looked at required at least two connections before finally arriving in Puerto Natales.

Normally, I avoid flights with that many segments whenever possible. If I can book a nonstop flight, I almost always will.

With multiple flights came multiple opportunities for something to go wrong, so I made the decision that we’d rent our trekking poles once we arrived in Puerto Natales instead of checking our bags.

At the time, it simply felt like the lower-risk option.

Looking back, I’m really glad we made that decision. Whether or not our checked bags would have arrived on time is impossible to know, but with several flights between home and Patagonia, removing baggage from the equation gave me one less thing to worry about.

The Layover Problem

Our connection through Santiago was easily the highest-stress part of the entire trip.

On paper, a 1-hour and 50-minute layover seemed reasonable.

In reality, it barely was.

After landing, we made our way through passport control, left the international terminal, walked across to the domestic terminal, and headed for the LATAM ticket counters.

It was there that we realized we couldn’t obtain our boarding passes. Every attempt to use the airline’s self-service kiosks produced the same error, so we hoped someone at the ticket counter could help.

That should have been the easy part.

Instead, we found ourselves repeatedly asking airline staff where to go after the kiosks kept producing the same error. Each time, we were directed somewhere else, only to end up right back where we started. We explained that we still needed our boarding passes, yet no one seemed able to direct us to someone who could actually resolve the issue. At one point, with only about 20 minutes remaining before departure, we were even told that we might simply miss our connection.

That’s when Dan stepped in.

Dan is typically pretty patient, which probably comes with the territory of being a teacher, but he also has a very low tolerance for needless incompetence. Once he realized we were just being sent in circles, his patience disappeared, he became much more assertive, and almost immediately someone finally took ownership of the situation. Within minutes, our passports had been manually verified and our boarding passes were printed by an agent with that authority.

From there, it became a race.

We cleared security, hurried across the terminal, and reached our gate with roughly 10-15 minutes to spare. Boarding was already underway.

We made the flight.

Only afterward did I learn that this appears to be a fairly common issue on some Delta/LATAM itineraries. Because the ticket was booked through Delta while the connecting flight was operated by LATAM, the two systems didn’t always communicate cleanly, requiring passengers to have their passports verified in person before boarding passes could be issued.

To this day, I still think about that experience and how, if Daniel hadn’t been with us, we probably would have missed our connection. The technology failing didn’t frustrate me nearly as much as being bounced from person to person, each unable or unwilling to take ownership of what turned out to be a remarkably simple problem.

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Thankfully, we had solid layovers on the way back:

Because our itinerary was booked through Delta but the first flight was operated by LATAM, neither Delta’s nor LATAM’s app allowed us to complete check-in online. Instead, we were forced to stand in a long airport line so an agent could manually verify our passports and issue paper boarding passes. Judging by the length of the line, we certainly weren’t the only ones dealing with it.

Unfortunately, the delays didn’t end there.

Despite having a six-hour layover in Santiago, we used virtually every minute of it. After receiving our boarding passes, we still had to clear border control, go through security, and make our way across the airport to our gate.

Just when we thought the ordeal was finally over, we encountered yet another document check. Ironically, it was administered by the very same agent who had issued our boarding passes earlier. That was immediately followed by another security screening at the gate itself. Our bags were searched again, and we were even forced to throw away bottled water we had purchased inside the airport after already clearing security.

To be fair, airports, security procedures, and airline operations change over time, so your experience may be different. But based on our experience, I would strongly recommend building in a generous layover if you’re connecting through Santiago. What looked like an opportunity to relax quickly turned into one long sequence of lines, checkpoints, and document verifications.

Of all the airports I’ve traveled through, Santiago was (still to this day!) the most logistically challenging.

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Transportation to Torres del Paine

Reaching Puerto Natales and the Park

Puerto Natales is the primary staging city for Torres del Paine. As discussed earlier when choosing our flight route, you can often find cheaper flights into Punta Arenas. The tradeoff is that you’ll typically spend the better part of a day getting to Puerto Natales, including a 3- to 4-hour bus ride and any waiting time between your flight and bus departure.

The typical sequence is:

1. Fly into Puerto Natales.
2. Stay overnight in town.
3. Purchase any needed food, fuel, and gear.
4. Take a morning bus to Torres del Paine.
5. Begin the trek from the appropriate entrance or trailhead.

There is no single free public transportation network inside the park. Travelers use scheduled buses between Puerto Natales and park entrances, private shuttles in certain sectors, and the Lake Pehoé ferry for itineraries involving Paine Grande typically related to hiking the W trek. Current schedules and routes should be checked directly before travel as they can change between seasons.

For the sake of transparency, and in case it helps with your own planning, here’s the bus reservation we successfully used to get into Torres del Paine:

One nice surprise about Puerto Natales is just how walkable it is. Once you’re in town, you can comfortably reach hotels, restaurants, grocery stores, and the bus terminal on foot, so the only taxi ride we needed was between the airport and Puerto Natales.

The bus itself, however, was a little more confusing than I expected.

Once we arrived at the terminal, several buses were loading passengers at the same time. The easiest way to identify the correct bus was by matching the departure time and destination on your reservation. The drivers were helpful, but in our experience they spoke little to no English, so there was a bit of trial and error while we figured out the process. It’s nothing to stress over, but it’s one of those little details that’s nice to know before you arrive to this chaotic scene.

Shuttle Bus

Once you arrive at the park, there’s a shuttle that takes you from the bus stop to the actual park entrance. At first, this seemed a little odd to me since I assumed the bus would drop us off directly at the entrance.

One important thing to know is that the shuttle was cash only when we visited, so make sure you have some Chilean Pesos with you. Otherwise, you’ll likely be walking the remainder of the distance (about 4.3 miles one way). I don’t remember the exact fare, but it was relatively inexpensive.

It’s also worth planning enough time for your return trip. After finishing the trek, you’ll need to catch the shuttle back to the bus stop before boarding your bus to Puerto Natales. Missing the shuttle could easily cause you to miss your bus as well.

I booked both of our Bus Sur tickets online ahead of time, although I remember hearing that you could also purchase return tickets from the Welcome Center if needed.

The Scheduling Mistake

I mistakenly assumed we could land in Puerto Natales and take an evening bus directly into Torres del Paine.

We could not, though thankfully I noticed when booking the bus that there were only morning departures into the park.

Meaning we had to remain in Puerto Natales overnight. Since all of our campsites were date-specific, this did not merely add a hotel night. It shifted our entire relationship with the trail.

So, I consolidated the first two hiking sections into a single 19.6-mile day.

This was the best place to do it because:

• The campsite we skipped belonged to the other operator, allowing us to maintain Vértice Patagonia’s required campsite progression while still keeping all of our reservations valid.
• We would be starting the trek with fresh legs.
• The terrain was much more forgiving than any other section later in the trip.

It was not ideal, but it worked.

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Additional Planning Considerations

Park Admission

The park entrance fee is separate from your campsite reservations, which is fairly typical for national parks. I would strongly recommend purchasing your entrance pass in advance. The in-person process looked considerably more confusing than I would have expected, and I think anyone would rather deal with confusion from the comfort of home than standing in line at the entrance to the park.

For reference, this is what an official Torres del Paine National Park entrance pass looks like:

Fuel

Fuel cannot be transported on commercial flights, so if you plan to cook, you’ll need to purchase it after arriving in Puerto Natales.

That said, for this particular trip you can realistically get by without a stove at all, provided you’re comfortable eating a cold meal at Los Perros, the only campsite where meal service wasn’t available when we booked. I went back and forth on whether it was worth bringing one, but ultimately decided to pack my stove because we’d be spending New Year’s Eve at Los Perros. If there was ever a night I wanted a hot meal, that seemed like it.

Accommodations

Date	Main Group	Dan
Dec. 29	Hotel Vendaval • Twin beds (4) • Breakfast included	Same
Dec. 30	Dickson • Campsite • Dinner & Breakfast included	Same
Dec. 31	Los Perros • Campsite • Dinner & Breakfast not included	Same
Jan. 1	Refugio Grey • Campsite • Dinner, Breakfast & Lunch included	Same
Jan. 2	Paine Grande • Campsite • Dinner & Breakfast included	Los Cuernos • Bed in Cabin • Dinner & Breakfast included
Jan. 3	Los Cuernos • Bed in Cabin • Dinner & Breakfast included	Hotel Big Sur • One Full Bed • Breakfast included
Jan. 4	Chileno • Suspended Campsite • Dinner & Breakfast included	—
Jan. 5	Airbnb • Three beds • Breakfast not included	—

Campsite Amenities

This was the best visual summary of the amenities available at each campsite in Torres del Paine National Park that I came across while planning the trip. Unfortunately, I no longer remember where I originally found it, so I can’t properly credit the creator. If this happens to be your work, please let me know and I’d be happy to add attribution. In the meantime, I’ve included it because it was by far the most useful breakdown I found.

Bag Storage

One thing that makes any backpacking trip more enjoyable is having a place to leave everything you don’t need on the trail, like clean clothes, travel gear, or anything else you don’t want to carry backpacking for a week.

Hotel Vendaval offered luggage storage as part of our stay. That alone made it an easy recommendation, but it also happened to be one of the nicest places we stayed in Puerto Natales. The rooftop terrace offered fantastic views over the city and made for a great place to relax before heading into Torres del Paine.

I didn’t stay there on our return trip—not because there was anything wrong with it, but because I generally like trying new places whenever I travel. If you prefer convenience over variety, though, I wouldn’t hesitate to book Hotel Vendaval for both the beginning and end of your trip.

Gear Rental

As discussed earlier when covering our flight route, we decided to rent trekking poles in Puerto Natales to avoid checking our bags due to the number of flight connections. As I also mentioned, if you opt to travel with only a carry-on, I’d also recommend renting tent stakes as well since they’ll almost certainly be confiscated by airport security on the way home if you bring your own.

One thing I wouldn’t recommend is reserving the gear in advance.

We did exactly that. At no point was it communicated that the shop would be closed on our scheduled pickup day. I know it sounds silly to assume a business would be open on the date listed in its own confirmation email, but as you can see below, our pickup date was literally for that day.

When we arrived, the shop was closed.

We had no choice but to rent from another outfitter to stay on schedule. I later explained the situation and requested a refund, but never received one.

To this day, I still can’t believe it. It seems like such an obvious expectation that if a business lets you reserve equipment for a specific date, it should actually be open on that date.

Anyway, this is the outfitter we ended up renting from instead. Their hours were much more accommodating, and the entire process went smoothly. After explaining what had happened, the employee was kind enough to give us a discount on our rental. Based on that experience alone, I wouldn’t hesitate to recommend them if you’re looking to rent backpacking equipment in Puerto Natales:

Food

Our food plan was a little different than our usual backpacking trips.

To make this trip as vacationy as possible, we opted for half board at every campsite where it was available. The goal was simple: carry as little food and cooking equipment as possible to have a lighter experience in one of the most beautiful parks in the world.

If I were planning the trip again, though, I would opt for full board instead.

Speaking of half/full board, one thing that’s worth mentioning is that dinner isn’t served whenever you arrive. The refuges schedule hikers into different dining times, presumably to keep the kitchen and dining area from becoming overwhelmed.

Because we hiked nearly 20 miles on our first day, we arrived after our assigned dinner time. Thankfully, the staff was incredibly accommodating and still found a place for us, but until that moment I hadn’t realized meals were scheduled in advance rather than simply served on demand.

Since they went out of their way to squeeze us in, I used some of the heavy Chilean coins I’d been carrying around to leave a tip as a thank-you. They genuinely seemed to appreciate the gesture, and I was happy to finally put those coins to good use 😅

The snack options available for purchase were pretty limited, and considering how popular Torres del Paine has become, it really isn’t worth the headache of trying to piece meals together yourself. The additional cost is well worth the convenience.

Snack options with photos (courtesy of Backcountry Emily):

Refugio / Campsite	Food Information
Refugio Dickson	https://backcountryemily.com/ocircuit-campground-guide/#Dickson
Camping Los Perros	https://backcountryemily.com/ocircuit-campground-guide/#Los_Perros
Refugio Grey	https://backcountryemily.com/ocircuit-campground-guide/#Grey
Refugio Paine Grande	https://backcountryemily.com/ocircuit-campground-guide/#Paine_Grande
Refugio Los Cuernos	https://backcountryemily.com/ocircuit-campground-guide/#Cuernos
Refugio Chileno	https://backcountryemily.com/ocircuit-campground-guide/#Chileno

This was by far the best resource I found for previewing the snack options at each refuge. The official operators mention that food is available, but they don’t really show what that means in practice. Having photos of the actual shelves and menu items made it much easier to decide how much food we needed to carry. That said, as I mentioned earlier, if you opt for full board, you’ll have much less need to rely on these snacks in the first place.

Our original plan was to avoid carrying stoves altogether.

Unfortunately, after everything had already been reserved, I discovered that Los Perros, the campground before crossing John Gardner Pass, didn’t offer meal service, so we ended up carrying our stoves just for that one night. We could have settled for a cold meal, but it also happened to be New Year’s Eve.

Interestingly, when we actually arrived at Los Perros, there were some limited meal options available for some of the campers there. To this day, I’m still not sure how those were available. I had booked our reservations as early as I possibly could, and at the time there was no option whatsoever to reserve meals there. Whether they were added later, held back for walk-up purchases, or something else entirely, I honestly don’t know.

I should mention that the food is fairly basic for the price 💸 You’re definitely paying for convenience more than culinary excellence. That said, you’re also in the middle of nowhere, and someone has to transport all of those supplies into the park. Looking at it from that perspective, I’d still happily pay the premium rather than carry the extra weight myself.

Water

Water was plentiful throughout the trek. Every campsite we stayed at had running water, and to the best of my recollection, I don’t think we ever even used our water filters.

If you’re looking for the most reliable information on water sources along the trail, FarOut (previously known as Guthook) is hands down the best resource I’ve found—not just for Torres del Paine, but for nearly every long-distance trail I’ve hiked. While rivers and streams often appear on standard maps, FarOut goes a step further by not only documenting water sources but also including comments from other hikers about their reliability, seasonal conditions, and recent flow. That community feedback alone has made it one of the few apps I now consider indispensable for backpacking.

The only downside is that FarOut doesn’t have every long-distance trail in the world. Their library is extensive, but it isn’t all-encompassing. Fortunately, Torres del Paine is one of the most popular backpacking destinations on the planet, so the park is exceptionally well covered. If you’re planning this trip, I wouldn’t hesitate to purchase the map.

Weather

Patagonia is famous for rapidly changing weather and relentless wind.

Summer does not mean reliably warm or calm. We packed expecting cold rain, strong wind, freezing overnight temperatures, and even the possibility of snow at higher elevations.

Thankfully, we never experienced the extreme winds Patagonia is known for, and it never snowed during our trip. Instead, the conditions felt much more like a typical fall backpacking trip in the States, which was exactly what we had prepared for.

Specialized Gear for Torres del Paine

• Rain jacket and rain pants – Weather can change quickly.
• Microspikes – We ultimately decided not to bring them because I was monitoring snow conditions through other hikers’ Instagram posts leading up to the trip. Had there been any significant snow accumulation, we absolutely would have packed them.
• Waterproof pack liner – Much lighter and more reliable than relying solely on a pack cover.
• Typical fall backpacking clothing – Gloves, insulating layers, and a warm hat were all worthwhile.
• Sun protection – A sun hoodie, sunglasses, sunscreen, and a hat are still important despite the cooler temperatures.
• Eye mask – Around the time of our trip, Patagonia received roughly 17 hours of daylight, which could make it surprisingly difficult to fall asleep if you’re sensitive to light.
• Trekking poles – Highly recommended, especially for the descent from John Gardner Pass.
• Cold-weather sleeping system – Nights were cold enough that I wouldn’t want to cut corners here.
• Satellite communicator – Cell service throughout the park was either nonexistent or extremely limited.

Dangerous Animals

The park is home to pumas, but encounters are uncommon, especially along the well-traveled O Circuit where they generally avoid groups of hikers.

I never felt there was a need to carry any form of protection. While puma sightings in the region have become more common in recent years, they still tend to avoid areas with regular human activity. As long as you’re following park regulations, staying on the established trails, and camping in the designated campgrounds, the risk of an encounter is very low.

Emergency Communication

Cellular service could not be relied upon throughout the circuit.

One thing I honestly don’t remember is whether we had a formal contingency plan once Dan split from the group.

Whenever we separated during the trip, we would always agree on when and where we’d meet back up. Dan’s situation was a little different, though, because once he broke away from our itinerary, he was effectively on his own until he returned to Puerto Natales.

To prepare for that, I gave him printed copies of every reservation, ticket, and itinerary inside a water-resistant envelope. My thinking was simple: if something happened and he couldn’t reach us, he’d have everything he needed to solve the problem himself.

I vaguely remember Dillon bringing a Garmin inReach, so it’s possible we could have communicated through that if absolutely necessary. If we had a formal plan around it, though, I honestly don’t remember what it was.

Thankfully, none of it mattered.

From everything I heard afterward, every reservation was completed as planned.

Then again, that’s also the benefit of traveling with competent people. You don’t have to create a contingency plan for every imaginable scenario because everyone is capable of figuring things out when something unexpected happens.

Ironically, I’m probably the one who struggles with that the most. My mind naturally gravitates toward worst-case scenarios and every possible outcome, and while that tendency has undoubtedly helped me plan trips like this, it can also become a source of unnecessary anxiety. If I’m not careful, I can spend so much time thinking about everything that might go wrong that it starts affecting the group’s morale.

Over the years, I’ve learned there’s a balance. Plan for the things you can reasonably anticipate, then let go, trust the flow, and trust the people you’re traveling with.

The Time Zone Surprise

One thing that completely caught me off guard during planning was Chile’s time zone. Looking at a map, I assumed Patagonia would be on roughly the same time as the U.S. East Coast, or perhaps only an hour ahead. Instead, Chile was actually two hours ahead of Eastern Time during our trip. It felt strange considering how far west the country sits geographically, but Chile chooses to observe a time zone farther east than you might expect. It’s a small detail, but one worth knowing when coordinating flights, hotel check-ins, or communicating with people back home.

Cash and Cards

Chile uses the Chilean Peso (CLP).

I personally carried $500 USD worth of Chilean Pesos for the duration of the trip.

We primarily carried cash as a backup, but to the best of my recollection, most campsites accepted credit cards. The only times I remember needing cash were for the shuttle from the bus stop into the park and for the refuges in the remote northern side of the park. We only used cash a few times during the entire trip.

Like most of my international trips, I make moves to exchange money at a local bank in the United States before I travel. I don’t worry too much about getting the absolute best exchange rate because I’d rather have local currency in hand than spend time searching for an ATM after I arrive. Since that’s what I do, I don’t really have any recommendations for the best places to withdraw cash in Chile.

One important tip if you’re using a credit card abroad: always choose to pay in the local currency. If you’re given the option to pay in U.S. dollars, decline it. That’s called Dynamic Currency Conversion (DCC), and it allows the merchant to determine the exchange rate, which is almost always worse than letting your credit card issuer handle the conversion.

If you’ve never traveled internationally before, it’s also worth checking whether your credit card issuer recommends submitting a travel notification. Years ago, this was standard practice. However, when preparing for a more recent trip, I noticed that Chase, Wells Fargo, and American Express no longer required one for my cards. Policies can change, so it’s still worth verifying before you leave.

Finally, if you plan on withdrawing cash from an ATM overseas, I highly recommend using a Fidelity Cash Management or Charles Schwab Investor Checking debit card. Both are well known for reimbursing ATM fees worldwide, which can save a surprising amount over multiple trips. As an added bonus, Fidelity also pays interest on the cash sitting in the account.

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Group Expenses

Keep in mind that these costs will almost certainly change over time due to inflation, pricing changes, and the operators continually adjusting their reservation systems. Even so, this should provide a reasonable ballpark estimate of what you can expect to spend on the O Circuit if you plan it similarly to how we did.

It’s also worth mentioning that this spreadsheet only covers our pre-trip group reservations. Additional expenses such as restaurants in Puerto Natales, taxi rides, shuttle transfers, souvenirs, snacks, and other miscellaneous purchases are not included. I may have tracked those expenses elsewhere, but if I did, I haven’t been able to find that breakdown.

One thing I had hoped to include was the cost of airfare, but it appears we settled those expenses before I created this spreadsheet. Fortunately, I booked several of the flights using a credit card that earns 5.5% cash back on airfare, and I subtracted each person’s cash back from their total. Because of that, you can work backward to estimate what at least Conor and Dillon paid for their flights.

For example, Conor’s cash back was $83.62. Dividing that by 5.5% tells us his original airfare was approximately $1,520.36.

Flight Cost = Cash Back ÷ 0.055
$83.62 ÷ 0.055 ≈ $1,520.36

One final observation: book your flights early.

I purchased my ticket as soon as I was comfortable committing to the trip and ended up paying roughly $1,200. From what I remember, Dillon booked only about a day after I did, while Conor waited roughly another week before purchasing his ticket. Based on his cash back, Conor’s airfare worked out to approximately $1,520, illustrating just how quickly airline prices can increase.

For a trip like this, airfare can easily become one of the largest expenses, making it one of the easiest places to save a significant amount of money simply by planning ahead and booking as early as you’re comfortably able.

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Reflections on Planning and Preparation

What Worked

• Flying into Puerto Natales reduced overland travel and made getting to the park significantly easier than flying into Punta Arenas.
• Keeping offline and printed copies of every reservation provided valuable redundancy whenever internet access was unavailable or we needed to quickly reference a booking.
• Centralizing all group expenses eliminated the headache of everyone making separate reservations and trying to coordinate payments throughout the planning process.
• Designing two itineraries instead of forcing one allowed Dan to join the trip without requiring everyone else to hike mileage they weren’t comfortable committing to.
• Booking meal plans at the refuges dramatically reduced the amount of food we needed to carry and made the overall experience much more enjoyable.
• Storing our extra luggage in Puerto Natales allowed us to enjoy the trek with lighter packs while still returning to clean clothes and comfortable travel gear for the trip home.

What I’d Do Differently

• Use a third-party reservation service. After dealing with two separate operators, different booking systems, hidden costs, and confusing reservation rules, I genuinely think paying someone to coordinate everything would have been worth it.
• Add an extra day at the beginning of the trek. The 19.6-mile first day was entirely self-inflicted. I hadn’t realized buses into Torres del Paine only operated in the morning, and if I were planning the trip again, I’d simply add another day instead of forcing such a long opening hike.
• Research every airport, airline, and layover more thoroughly. This trip taught me how important it is to understand airport logistics, airline partnerships, and minimum connection times before purchasing flights.
• Don’t assume “confirmed” means “open.” We had reserved trekking poles well in advance and received confirmation, only to arrive on the scheduled pickup day and find the shop closed. Thankfully, we found another solution, but it was a good reminder to have a backup plan for essential gear.
• Always carry your PDI (Tourist Card) with you. When you enter Chile, immigration gives you a small paper called the PDI. It looks almost like a receipt, making it easy to overlook, but you’ll need it throughout your trip. Many accommodations request it at check-in to exempt foreign visitors from Chile’s tourist tax. If you don’t have it, you’ll generally have to pay the tax. You’ll also need the document when leaving Chile, so treat it like your passport and keep it on your person rather than leaving it with your luggage.
• Rent or purchase tent stakes after arriving if you’re traveling with only a carry-on. Airport security confiscated my tent stakes on the return trip, along with my small 2-inch scissors. It seemed excessive, but those were the rules.
• Choose full board instead of half board. The snack selection at the refugios was much more limited than I expected. Looking back, paying a little more for full board would have been worth it, especially considering how remote the park is.

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Alas, the Trip!

December 28–29: Getting to Patagonia

Photography Note: This post combines my own photos with images captured by other members of our group. Thanks to Conor, Daniel, and Dillon for allowing me to use their photos to help document the trip.

A Quick Note: By the time I finally sat down to write this, about a year and a half had passed since we hiked the O Circuit. Like most trips, I still remember the highlights, whether they were incredible or frustrating, but many of the smaller details have naturally faded with time. As a result, this part of the story is told largely through the photos and videos we captured along the way. Hopefully they help fill in the blanks where my memory doesn’t.

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I knew getting to the southern tip of Chile was going to be a journey, but I completely underestimated how terrible an airport experience could be. Santiago managed to turn what should have been a routine connection into one of the most stressful parts of the entire trip. Rather than repeat the story here, I’ve already documented everything that happened in “The Layover Problem“ above as part of the travel logistics.

Looking back, I think this is exactly why I spend so much time planning these trips.

Planning doesn’t eliminate problems. It simply reduces the number of variables you have to solve when something inevitably goes wrong. Even though Santiago threw us a curveball, having our reservations organized, offline copies of our itineraries, and a clear understanding of what came next kept a stressful situation from becoming a trip-ending one.

By the time we finally landed in Puerto Natales, it felt like we’d already accomplished something.

For nearly a year, this place had existed only on Google Maps, reservation websites, weather forecasts, and spreadsheets. Now we were actually here.

We checked into Hotel Vendaval, reorganized our packs one last time, grabbed dinner, picked up rental gear, and enjoyed our last night in town before spending the next week hiking through Torres del Paine.

Restaurante Ñandu

Hotel Vendaval‘s roof deck

The conversations had finally shifted away from flights, reservations, and logistics.

For the first time since planning had begun months earlier, we were simply present.

December 30: Welcome Center to Dickson

As mentioned above in planning, I made a miscalculation thinking that we could take the bus in the evening, so I pushed our group to hike a nearly 20 mile day from the start. This said, I opted for the earliest possible bus that would allow us to get to Camp Dickson before the dinner interval was over, meaning we had only 15-20 minutes to eat breakfast, walk to the bus stop (1-mile away from our hotel). This is actually one of the big reasons I added a buffer day at the start of our Lofton Traverse hike. While our group is more than capable of a 20 mile day, it really wore some of us out.

I think this was the only day it had rained the entirety of the trip, which is probably luck looking back. There was zero coverage from the sun and at the pace we needed to keep up with to make dinner starting the trail at 10AM is quite brisk. Thankfully again, this was the easiest section of the entire trail to execute a ~20 mile day.

Camp Dickson

I don’t have many photos after dinner, which probably means we turned in shortly afterward. After a long day of hiking through rain, we were still damp enough that every time the front door opened, the cold air seemed to cut right through us. Since our table was right by the entrance, each gust only reinforced the idea that our sleeping bags were probably the warmest place to be.

December 31: Dickson to Los Perros

I remember this section of the trek feeling incredibly easy. We slept in, took our time over breakfast, and had a relaxed start to the day before heading out.

Dillon managed to snag a video before I could get my phone out

To my knowledge, horses are used to transport food and supplies to the campsites that aren’t accessible by ferry. I’m not sure if there are additional supply routes elsewhere in the park, but we primarily saw them on the northern side of the O Circuit.

We eventually made it into camp, but I honestly don’t remember much from the rest of the day other than the fact that it was New Year’s Eve.

January 1: Los Perros to Grey

Our up, up, up day… and the first day of 2025! 🥳

I remember passing nearly everyone from our campsite that morning, which honestly surprised me because we weren’t moving particularly fast. We had simply started later than just about everyone else. If I remember correctly, the campsite required hikers to be out by around 9:00 AM, and we pretty much left right at 9:00. That meant we spent much of the morning gradually catching and passing people who had already been on the trail for quite a while.

John Gardner Pass was the reason I was glad we chose the O Circuit.

The climb itself demanded our full attention, but the moment we crossed the pass, Grey Glacier appeared below us. It did not look like a normal feature of the landscape. It looked like the landscape had opened into another world.

The descent was rough. Honestly, if someone asked me why I recommend trekking poles for Torres del Paine, this section of the trail would be my answer.

The views on this part of the hike were unlike anything I had ever seen. Completely spectacular! 😍

One of two bridges crossing what looked like glacier-carved gullies.

Thought it was an appropriate time to offer everyone some gum 😂

A few weeks before this trip, I visited Meow Wolf in Las Vegas after a backpacking trip to Havasupai. One of the exhibits featured a fake grocery store filled with parody products, and I could not resist buying it for Patagonia…it was well worth the extra weight 😂

I vaguely remember a few members of our group running low on food and snacks. That experience changed the way I estimate food for future trips. Rather than telling people exactly how much food to bring, I now only provide a ballpark estimate based on the mileage for each map and let everyone adjust from there. I naturally eat significantly less than some of my friends, so I actually ended up giving some of my food to the party members who required the extra sustenance towards the end of this day.

Camping situation

Reaching the W portion of the park felt like reentering civilization. After the quieter northern circuit, the number of hikers increased noticeably.

I vaguely remember asking during check-in for the earliest breakfast available since one member of our group planned to leave early the next morning. I honestly don’t remember whether that was easy to arrange or not. My guess is that it was, because if it had been especially difficult, I think I would have remembered it along with everything else that made this trip challenging.

Grey’s Amenities

I remember Camp Grey being one of the nicer refuges on the trek, even featuring a bar. If I remember correctly, it had been remodeled not long before our visit, although don’t quote me on that.

After making it over John Gardner Pass, we had plenty to celebrate. It was New Year’s Day, and we’d just completed what I considered the hardest mandatory section of the O Circuit. Needless to say, I enjoyed a few more drinks than I normally would.

The food was pretty basic, but honestly I had no complaints. Not having to carry a week’s worth of backpacking food made every meal taste a little better.

January 2: Grey to Paine Grande

Woke up real early this morning…

I woke up so early that I waited outside for Dan to crawl out of his tent, somewhat creepily 😅 but completely intentionally (he wasn’t nearly as humored by it as I was). This was where Dan would split from the group and complete the remainder of the O Circuit over the next two days, so I wanted to make sure I caught him and handed off everything he’d need before we went our separate ways.

Before the trip, I had put together a folder containing everything Dan would need to finish the trek on his own and make it back to Puerto Natales. Inside were printed copies of all his reservations, sealed in a water-resistant document pouch. Knowing he could still complete the journey even if his phone died or something unexpected happened gave me considerable peace of mind.

After Dan split from the group at around 7AM, we settled into a much slower pace. Considering how short our day was, there really wasn’t any reason to rush. If I’m remembering correctly, I think we even took our time getting out of camp that morning.

Although I wasn’t there for Dan’s side of the journey, I have access to the photos he uploaded afterward. Judging by the timestamps, he had already made it to our destination for the evening just as we were leaving from Grey.

About to leave Grey (9:37AM)

Paine Grande

Camp was probably our most scenic yet. The deep blue water was quite the sight! 😍

Making moves to reduce exposure ☀️

The upstairs bar served some delicious cocktails made with a local berry called calafate. I’d describe the flavor as somewhere between a blueberry and a blackberry.

Looking back, I honestly don’t remember exactly how everyone was feeling, but I have a suspicion based on the photos that Conor may have been struggling more than I realized at the time. Dillon and I, on the other hand, were almost certainly having the time of our lives. It also made me appreciate just how much Daniel’s sense of humor had contributed to the group’s dynamic over the previous few days. As I mentioned earlier in the logistics section, Daniel always seemed to know how to keep everyone’s spirits up when things got gritty.

January 3: Paine Grande to Los Cuernos

This next section reminded me a lot of our first full day in Italy on the Tour du Mont Blanc. Personally, I still think the Italian Alps are even more beautiful, but there was something about these wide-open landscapes that brought me right back to that feeling. It’s difficult to put into words. Compare the photos and maybe you’ll see what I mean.

Shortly after this bridge, we reached Campamento Italiano, which wasn’t reservable (at least when we hiked the O Circuit) but did have potable water and bathrooms. Thinking back to my comment about how much this section reminded me of Italy, it’s kind of ironic that whoever named the campsite apparently had the same thought.

Anyway, this was when I realized Conor didn’t have it in him to commit to this completely optional section of the trail. Since he volunteered to stay behind and watch our packs, Dillon and I got to head up to the Británico Viewpoint carrying only our day gear. If you’re paying attention to the map, this is the hike that completes the middle leg of the “W.”

On the way back down, likely because of the pace we were moving, another hiker asked if we were trail runners. If I’m remembering correctly, I told him, “I’m pretty much off the couch.” Dillon immediately chimed in and explained that we’d both thru-hiked the Appalachian Trail, so we still had the muscle memory and were used to hiking at a pretty good pace.

Looking back, I still think my answer was more accurate. I spend most of my time “off the couch.” Hiking and backpacking are about the only cardio I consistently do. I know I should probably do more for the sake of struggling less, but no other form of cardio has ever been fulfilling enough for me to stick with.

We came back to find Conor taking a nap in a bush once we got back to Campamento Italiano 😂 In all fairness, he was clearly trying to escape the sun, but it was still hilarious to stumble across him like this.

On the way to the next campsite, he told us all about the lovely conversation he had with some passersby’s pre-bush 😂 I think Dillon and I were gone from around 11:30 AM until 3:00 PM, so he had plenty of time to establish himself as part of the local vegetation.

Didn’t expect to find a rocky beach out here.
Definitely a pleasant surprise! 🏖️

I had an idea of how nice these cabins would be, considering they were the only beds we’d have on the trail, but I never expected them to be this nice.

Post-trip, Daniel even mentioned that his experience was on par with something you’d find in Cabo. To be frank, I don’t know if I misheard him, but since I’m generally terrible with popular references, I looked it up afterward. From what I could tell, Cabo has a reputation for luxury resorts and upscale accommodations, which gives you an idea of just how impressed he was with these cabins.

Oh right, I do remember there being a bit of friction during check-in. This was my first time staying at a Las Torres Patagonia property, so it wasn’t obvious that I needed my PDI document beforehand. None of the Vértice Patagonia campsites had ever asked for it.

Since I didn’t have it with me, I had to pay the additional tourist tax at this check-in, as well as at the following Las Torres property. Honestly, it was a little frustrating because my passport clearly showed I wasn’t a Chilean resident. That said, the staff explained what I needed to do. Once I retrieved my luggage back in Puerto Natales, I took a photo of my PDI document, emailed it to the address they provided, and they refunded the tax without any issues.

In the end, everything worked out, but it definitely caught me off guard at the time. If you’re staying at a Las Torres Patagonia property, it’s worth keeping your PDI document handy so you can avoid this altogether.

This place gave me major Legend of Zelda vibes. I can’t really explain why—it just had that magical feeling that made it seem more like a video game than real life. It was unbelievably beautiful.

Checking out the Refuge where we checked in a bit more…

Waiting outside for dinner while the refugio staff finished setting up the dining room.

Dinner

Found some like-minded adventurers also committed to the O circuit

I really liked this refugio. It had a comfortable, cozy, homey sort of feel to it 🏡

Made moves to get some astrophotography shots…

January 4: Los Cuernos to Chileno

As you could imagine, the morning was as beautiful as the evening

I did not want to leave 🤩

But alas, it was time to hit the trail 😭

When Conor needed a hand, Dillon didn’t hesitate to shoulder a second pack – Absolute rock💪🏻

Looking back, this was one of those moments that reminded me how difficult it can be to judge how someone else is really doing. I have a hard time distinguishing between “I need a break” and “I genuinely can’t keep going,” mostly because of how I respond when I’m pushing myself.

On difficult hikes, I become incredibly vocal. This tramily (trail family) actually nicknamed me Sméagol because I turn into Gollum whenever I’m really pushing myself 😂 The difference is that, despite all the complaining I vocalize, I can almost always keep going.

Not everyone expresses fatigue the same way, and I have to be careful to remember that when I invite people on trips like this.

Conor was different. I knew he was capable of completing this trek, which honestly made it harder for me to recognize how much he was actually struggling in the moment. That’s one of the reasons I appreciated Dillon stepping in without hesitation. Rather than debating how tired someone was or waiting to see what happened, he simply took action and carried a second pack.

Dillon is just that kind of person 🪨

Arrived a little early, so we had some time to relax before check-in.

Very happy I made moves to get our own tent for each of us, considering how tired some of us were…

Conor be done ⚰️

With some extra time to spare, I decided to follow Dillon (whom I never actually caught up to) to check out the crown jewel of Chilean Patagonia, Mirador Las Torres. Unfortunately, by the time I made it up there, I discovered I had hiked roughly 2.5 extra miles only to find the viewpoint closed. What made it especially frustrating was that every sign I had passed on the way up listed the closing time as 6:00 PM, yet the viewpoint itself had already been closed since 3:00 PM.

In the end, I had walked an extra five miles for very little.

Looking back, this was probably my only real regret from the entire trek. I wish I had just relaxed at camp instead of chasing one more viewpoint.

The reason I never caught Dillon was because he had continued hiking with Rakia from the group we had meet at the previous Refuge. They decided to continue past the closure to see if they could get a better angle of the towers from farther up the trail. I wandered a little beyond the closure myself, but nowhere near as far as they did.

This was about the best view I was able to get before turning around:

Dinner here was a bit different from the rest of the meals on the trail. Rather than focusing on quantity, it felt more like a culinary experience. While I appreciated that, I still found myself buying snacks afterward to fill the gap. It felt more like a meal prepared for tourists than one designed to fuel backpackers after a long day on the trail.

Definitely the most culinary dinner experience of the entire trek

Though speaking of touristy vibes, these were the nicest showers 🚿 on the entire trail ❤️‍🔥 even in comparison to our really nice previous night where we had our own shower quarters separate from the rest of the refuge.

Chileno’s shower situation

Right before we went to sleep, Dillon let us know that Raki had invited us to join their group for the sunrise hike to Mirador Las Torres. For clarity, this group consisted of Arielle, Nat, Raki, and Sarah, whom we had met at the previous refuge and I keep referring to throughout this post simply as “the group we met at the previous refuge.” After talking it over, Dillon and I decided to commit.

I really wanted Conor to come with us, but he told me he had already made peace with skipping it and asked me to respect that decision. At the time, I was a little disappointed knowing he’d miss what most people consider the grand finale of the O Circuit and arguably its most iconic viewpoint.

Looking back, though, my opinion changed. After seeing Mirador Las Torres, I still thought Grey Glacier was the more impressive experience. Once I got back, I no longer felt bad that Conor had decided to skip the sunrise hike.

January 5: Return to Puerto Natales

As we had discussed the previous evening, our group and our newfound trail friends decided to wake up well before dawn—I think around 2:00 AM—to try and reach Mirador Las Torres for sunrise. Although the trail technically wasn’t open yet, it didn’t appear to be enforced the way the 3:00 PM closure was.

It was quite cold but worth!

The only real downside was that I had brought my camera gear hoping to do some astrophotography, but I wasn’t able to get the shots I had envisioned. Ironically, the best photos ended up coming from my phone. By the time we reached the viewpoint, the sky had already brightened enough that my setup wasn’t ideal. Looking back at the images, I can still make out a few stars through the clouds, but nowhere near enough to capture the scene the way I had hoped.

My best shot

Because of the cloud cover, we never got to see the infamous sunrise light hit the tips of the granite spires. We actually left a little early, and apparently there was a brief moment afterward when the sun finally broke through. Honestly, I didn’t feel like I missed much. I didn’t even realize that was what everyone was waiting for until I got up there.

That said, it would still be nice to see it someday under better conditions. I’m generally not someone who revisits destinations—there are simply too many places in the world I still want to see—but Martina has already told me she’d love to hike to this iconic viewpoint.

Honestly, writing this blog has me entertaining the idea of going back. Fall was my original preference when planning this trip, and seeing Patagonia in that season with Martina while exploring more of Chile sounds pretty appealing.

When we were back, I went back to sleep for a nap, I think woke up to eat breakfast, and then get packing, only for Dillon to find me asleep again. I was beyond tired and I would not be surprised if I slept on the bus that took us back to Puerto Natales.

Conor seemed completely rejuvenated for our trek back to the Welcome Center. Whatever rest he got the day before was exactly what he needed.

Those granite spires in the distance looked way bigger from further away than they did up close

Made it back to the Welcome Center

Met up with a few people we had been on and off hiking with during the second half of our trek.

I think it was here that we realized just how many people our age on the O Circuit worked in tech. Somehow the conversation drifted toward work, and it turned out most of the group we had been hiking alongside worked for well-known tech companies. Looking back, it’s kind of crazy that we all ended up crossing paths in such a remote corner of the world.

Photo by Arielle

By the way, remember the calafate berry I mentioned earlier as the main ingredient in the cocktail from Paine Grande? They had straight calafate juice at the Welcome Center, and I kid you not—I downed three of these! 😂

Highly Recommend!

I don’t remember too much to about the buses other than waiting for a while, but I think that was largely due to the how early we finished the trail for the day.

The only thing I really remember while we were waiting was Arielle’s surprise at how little we had paid for our flights. I don’t remember the exact figure anymore, but hearing her reaction was a nice bit of validation that all those hours of early planning had been worth.

I remember the bus ride being smooth, and as soon as I got cell service, my phone filled with New Year’s messages from friends and family. That was also when I realized I still hadn’t received any check-in instructions for the Airbnb we had reserved, which sent me into a brief panic.

Thankfully, everything worked out once we arrived. I had overlooked the fact that the host handled communication through WhatsApp, which is far more common outside the United States.

As soon as we dropped our bags, and showered we committed to some dinner 🤤🍴😋

El Brisket

And then dessert 🍨

I think this was where we split up for a while based on the number of photos I don’t have on my end of Conor interacting with the town’s stray looking dogs. I headed back to the Airbnb, while Conor and Dillon spent more time exploring the town.

Looking back, one thing I’ve come to appreciate about group travel is how important it is to have time apart. Even when everyone gets along, constantly being around other people for days on end can be mentally exhausting. I’m the same way. Sometimes you just need a little space to recharge.

I don’t mean that as a criticism of anyone. If anything, it was a lesson for me as the organizer. On longer trips, it’s healthy to build in opportunities for people to naturally do their own thing for a bit. Looking ahead to our longer Norway trek, that’s something I’ll be much more intentional about. Everyone has different social batteries, and giving people room to recharge makes the group stronger in the long run.

January 6-7: Return Home

Long story short, we got breakfast…

Had a fantastic omelet! 🙌🏻
Holaste! Specialty Coffee
Then went for a second breakfast…

Creperia Cafe & Te
…while waiting for our scheduled Uber to the airport…

and then boarded our flight to Santiago.

Once in Santiago, as I mentioned in “The Layover Problem,” our return through Santiago wasn’t nearly as stressful since we had a much longer layover. That said, we still managed to use virtually every minute of those six hours just making our way through the airport’s various lines, checkpoints, and document verifications before finally reaching our gate.

After getting back to the States, I finally felt like I could relax. It honestly felt like Santiago Airport had held us hostage both coming and going. After I got home, I looked around online to see if we had simply been unlucky, but it turned out plenty of other travelers had described similar experiences. That at least made me feel a little better knowing it wasn’t just us.

We arrived in Atlanta on the way home, so I stopped by the Centurion Lounge while waiting for our flight back to D.C. To my surprise, I ran into Sarah again. Crazy coincidence. We very much bonded over the fact that we were both the organizers of our trips.

God I love this lounge so much 🤤

Technically it is the following day, but since we were traveling, it felt like just one long day.

It turned out Dan got incredibly lucky. 🍀 Heavy snow rolled in almost immediately after he made it home, without affecting his travel. As a bonus, it even earned him two extra snow days before he had to return to work.

Thinking back, I guess we got pretty lucky too. Despite the storm, our route home wasn’t affected. From what I heard, everything had been cleared the night before we arrived. We both ended up just outside the weather window on both ends by pure happenstance.

Also, Daniel was kind enough to remove all the snow from my parents’ car before we arrived. It was a small gesture, but a very thoughtful one that I really appreciated 😊

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Closing Thoughts

The logistical difficulty of planning Torres del Paine was disproportionate to the distance we ultimately hiked.

The trail itself was challenging, but the greater puzzle 🧩 took place months before we ever reached Chile: two campsite operators, incomplete websites, strict reservation sequences, date-specific transportation, expensive accommodation packages, and an entirely separate itinerary designed to bring Daniel into the circuit during his winter break.

Somehow, it all worked ✅

I’m grateful that Dillon, Conor, and Daniel trusted me enough to commit to a trip before every detail had been solved. I’m especially grateful that Daniel trusted me enough to put his faith in the itinerary I had designed for him. That kind of trust isn’t something I take for granted, and seeing everything come together made the months of planning feel worthwhile. 🙏🏻

All of the maps, spreadsheets, reservation PDFs, emails, and contingency plans served a single purpose: to make the logistics disappear once the adventure began. By the time we reached Torres del Paine, the planning had already done its job, allowing us to focus almost entirely on the experience itself 🗺️

Looking back, I think the biggest takeaway wasn’t just the hike itself, but the confidence I gained from planning it. Torres del Paine was by far the most logistically complex trip I had ever planned, and successfully pulling it off gave me the confidence to take on our next adventure: the Lofoten Traverse in Norway 🇳🇴

I’ll save the details for another time, but to give you an idea of what we’ve committed to next, here’s a map of the route.

At first, I was tempted to swing the pendulum all the way in the opposite direction of Torres del Paine. After experiencing a trek where nearly every day was dictated by campsite reservations, I found myself longing for the freedom to simply show up, hike at our own pace, and camp wherever the day naturally came to an end.

The more I thought about it, though, the more I realized this wasn’t just my adventure. It was everyone else’s vacation too. There are tradeoffs that come with traveling as a group, and sometimes having nice things means committing to a schedule. So even though Norway could have been planned with complete flexibility, camping wherever we wanted without reservations, comfortable accommodations, predictable stopping points, hot showers, good meals, and the occasional opportunity to slow down and actually enjoy being on vacation were well worth sacrificing a little spontaneity.

While Norway didn’t require us to reserve places to stay, we chose to anyway so the trip could feel like more than one continuous backpacking grind. Part of me would still appreciate going in with very little of a plan, much like Dillon would prefer. In fact, Dillon is already locked in to plan our 2027 trek, so I have a feeling we’ll eventually get to experience exactly that kind of adventure.

After everything I learned from planning Torres del Paine, I feel much more capable of balancing those competing priorities. I’m incredibly excited for Norway, and judging by the amount of planning we’ve already done and the level of detail we’ve put into it, I know everyone else is excited too 🥾

If this blog has done its job, I’ve hopefully given you not only a look at what it’s like to hike the O Circuit, but also a roadmap for planning the trek yourself.

I’ll be sure to report back after the Lofoten Traverse. In many ways, it will be almost the complete opposite of Patagonia and unlike nearly every adventure I’ve experienced before. That’s exactly the kind of growth I was looking for. Planning Torres del Paine gave me the confidence to take on something entirely different, and the Lofoten Traverse feels like the natural next step in that journey.

Torres del Paine was wild, inconvenient, expensive, beautiful, and occasionally absurd 🏔️

And it was exactly the kind of adventure we were looking for ❤️

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Where I’ve Been

It’s been a long time since I’ve updated the blog, and honestly, life has changed in ways I never expected.

Over the past few years, life shifted heavily toward healing, connection, travel, growth, and actually living instead of documenting everything.

After Conor helped me figure out what was actually going on with me, I began healing from CPTSD. Looking back, it’s difficult to overstate how much that changed my life. I found myself living by a completely different set of rules than the ones I had unknowingly operated under for years. Relationships became easier. I could genuinely connect with people instead of simply understanding them intellectually. It felt like I had finally gained access to parts of being human that had always been there but somehow remained just out of reach.

Shortly afterward, I unexpectedly found spirituality.

For most of my life, I dismissed spirituality as vague nonsense. To my surprise, what I found wasn’t blind belief at all. At its core, it felt more like an ancient philosophy and psychology centered around awareness, perception, and the relationship between ourselves and everything around us. Like any field, there are plenty of ideas I don’t agree with, but the parts that resonated fundamentally changed how I experience life.

One realization in particular continues to shape me every day: we never interact with reality directly. We experience our interpretations of reality. Everything we see, hear, touch, and feel is processed through our own minds before we ever become aware of it. Whether someone agrees with that perspective or not, recognizing it completely changed how I respond to other people and to difficult situations.

I find myself carrying far less resentment than I used to. If someone lashes out at me today, I no longer instinctively see it as something being done to me. More often than not, I see someone acting from their own suffering, fears, or perceptions. That doesn’t mean every action is acceptable, but it has made forgiveness, patience, and empathy come much more naturally than they ever did before.

That awakening is still ongoing, and it has fundamentally changed how I prioritize my time. Somewhere along the way, I realized I wanted to spend more time living these adventures than documenting every moment of them. That’s one reason updates here have become less frequent. Instagram Stories have become my way of quickly sharing the journey while staying present enough to actually experience it.

While living that new life, I crossed paths with Martina, who is now my girlfriend. She is a postdoctoral neuroscientist studying neurons in the brains of rats. Most of her work is well above my head, but that has never stopped us from having incredibly deep conversations.

More importantly, we’re remarkably aligned in how we approach life. She has her own career, her own passions, and her own ambitions. We both value travel, experiences over possessions, and intentionally designing the lives we want to live rather than simply following the default path. We met through an event called Skip the Small Talk, which is probably the most fitting place imaginable for us to have met. Deep conversations are my default operating mode, and small talk has always felt like elevator music to me 😅

I won’t go much deeper for the sake of her privacy, but I wanted everyone who’s followed this blog over the years to know that life is genuinely going really well.

Around the same time, something else happened that I hadn’t expected for another three years.

Based on the math, I quietly reached financial independence before the end of 2025.

To be completely honest, I think the market deserves a fair amount of credit. Since 2021, it’s been an incredible run. But it wasn’t entirely luck either. For years, I had been intentionally building a system around spending, investing, taxes, travel, and designing a lifestyle that required less money than most people assume is possible.

A few friends eventually became curious how I was managing to aggressively save for retirement despite earning roughly a median U.S. income, traveling internationally, and still living comfortably on about $25,000 per year without feeling deprived.

As I started walking them through everything, I realized I hadn’t simply collected a handful of financial tips over the years.

I’d accidentally built an entire operating system.

I used to call it “retirement architecture,” but retirement isn’t really the goal anymore. What I’m actually pursuing is optionality.

To me, optionality means having the freedom to direct my time, attention, and energy toward what genuinely matters instead of always being constrained by financial pressure. If I want to disappear onto a long trail, spend months deeply studying a subject, travel somewhere new, or simply follow a meaningful rabbit hole, I want that decision to come from curiosity rather than necessity.

Ironically, becoming financially independent hasn’t made me want to stop working.

If anything, it’s changed why I work.

I know time and health are ultimately more valuable than money. That’s exactly why I’m prioritizing these long-distance hikes while I’m still young enough to fully enjoy them. At the same time, I genuinely enjoy building things and solving difficult problems. Financial independence simply means I can choose work because it’s meaningful rather than because I need it to survive.

The funny part is that I kind of feel like my own trust fund kid now. Not because someone handed me money, but because I spent years building that freedom myself.

Life also handed me an unexpected transition, giving me the opportunity to slow down and think carefully about what I want the next chapter to look like. Rather than rushing into the first opportunity that comes along, I’m using this time to travel, continue refining this financial framework, organize more ambitious adventures, and actively search for work that genuinely excites me.

Eventually, I plan to release the financial architecture publicly as a paid product. Not because it contains secret information—most of the underlying concepts are already available to anyone willing to spend enough time learning them—but because I’ve spent years organizing them into a coherent framework. The value isn’t in hiding information; it’s in the architecture, the iteration, and the time it saves people by giving them the building blocks to build that future for themselves.

If I can help even a handful of people reach the point where their basic needs are covered and they’re free to spend more of their lives pursuing what actually matters to them, I think that would be a pretty meaningful contribution.

For now, though, I’m simply grateful.

Grateful for the people in my life.

Grateful for my health.

Grateful for the freedom I’ve spent years working toward.

And grateful that the next chapter feels less like something I have to survive and more like something I get to create.

Other than that, I’ll probably continue spending most of my free time doing exactly what you’ve come to expect from this blog:

Planning the next epic adventure, then sharing everything I learned so you can do it yourself🤙🏻💚