Planning on Moments in the Miles

Eight Months in Southeast Asia: The Whole Honest Story

Mon, 23 Jun 2025 00:00:00 +0000

Eight months was the plan. We booked it that way on purpose, because the van had already taught us that the good stuff shows up after you stop moving, and three weeks in a country doesn’t buy you that.

What we didn’t plan was the shape it took. This part of the world keeps handing you one more reason to stay: one more bus to catch, one more village you’ve never heard of that turns out to be the one you’ll talk about for years.

We arrived in Bangkok in the fall with a rough route and eight months in front of us. We left from a tiny airport in Bali, heading to Switzerland to stay with two friends we’d met on a motorbike loop in northern Vietnam, people we hadn’t known existed when we landed. That felt like the right ending. Or maybe not an ending at all.

This is the full story: every country, every highlight, and the moments in between that don’t make the Instagram grid but make the trip. If you’re planning your own time in Southeast Asia, we hope this gives you something real to hold onto.

We also drew the whole route on our map, leg by leg. Fly the loop, then come back for the long version.

The route at a glance

If you want the whole eight months as a route rather than a read — every stop in order, with the nights we spent in each — that lives here: the full Southeast Asia itinerary.

Thailand

Bangkok — 8 days

We flew in from Mexico. Twenty-seven hours of travel time, door to door.

So the first few days in Bangkok were about adjusting and very little else. We slept a lot, at strange hours, and woke up starving in the middle of the night with no sense of which way anything was. That’s the honest version of landing on the other side of the world.

Once we came out of it, the city was immediately, overwhelmingly itself: dense and golden and chaotic in a way that makes you feel very small and very alive at the same time.

Eight days felt like both too long and not nearly enough. We wandered temples in the early morning before the heat settled in, ate our way through street food markets, and started to understand the rhythm that would carry us through the next eight months: wake up early, move slowly, say yes to things you don’t entirely understand yet.

Street-cart pad krapow. Say yes.

Chiang Mai — 26 days

We didn’t intend to stay in Chiang Mai for nearly a month. We booked a week and then kept extending. It’s that kind of place.

Chiang Mai

We moved through four different neighborhoods during our stay (Phra Singh, Hai Ya, Chang Khlan, and in and around the old city) and each one had its own texture. The old town with its moat and crumbling temple walls felt almost like a village. Chang Khlan buzzed with the Night Bazaar. Hai Ya was quieter, residential, the kind of place where you find a coffee shop that becomes yours.

The reason we were there for 26 days was partly the city itself and partly timing. We were there for the Yi Peng lantern festival, Loi Krathong, and if you’ve ever seen a photograph of thousands of paper lanterns lifting into a dark sky above a city and wondered if it could possibly be as beautiful in person, the answer is that it is more beautiful. It is one of the most extraordinary things we have ever witnessed. We stood in a crowd of strangers and launched a lantern together and didn’t say anything for a long time.

We also spent a day in the Mae Wang District to see elephants, ethically, at a sanctuary where they roam freely and you walk among them rather than ride them. We’re still not over it.

Pai — 1 week

A van carried us up through 762 curves of mountain road to Pai, a small town in the hills with a pace that undoes you a little. Countryside coffee shops. Hammocks. Rice fields. Long stretches of the day spent lounging and calling it a plan. We rented motorbikes and explored for a week.

We want to say this clearly: if you have been curious about riding a motorbike but haven’t done it yet, Pai is the place to learn. The roads are manageable, the traffic is forgiving, and the scenery is the kind that rewards you for moving slowly. By the end of the week we felt like we’d always known how to do it. That confidence would carry us a long way, including onto the Ha Giang Loop months later in Vietnam.

Chiang Rai & Chiang Khong

From Pai we made our way to Chiang Rai, stopping to see the White Temple (Wat Rong Khun) and the Blue Temple (Wat Rong Suea Ten). Neither photograph quite prepares you. The White Temple is all reflective glass and intricate white plasterwork; the Blue Temple glows electric in the late afternoon. We spent more time than we planned and didn’t regret it.

Chiang Khong was the edge of Thailand, a small border town on the Mekong where you catch the boat into Laos. We arrived expecting to spend one night. But the town had a quiet quality we liked, and by then we were learning to trust that instinct.

Laos

The slow boat — Pakbeng & beyond

The slow boat from the Thai border into Laos is a two-day journey down the Mekong on a long wooden vessel with rows of seats and views that scroll past like a painting you can’t quite believe is real. It is one of the most recommended experiences in Southeast Asia, and the recommendations are earned.

Sunset on the Mekong

We were supposed to stop one night in Pakbeng, the small river town at the halfway point, and continue to Luang Prabang the next morning.

We stayed two.

The reason was a man named Vieng. He managed our guesthouse and owned the bar down the road, and we met him the first evening with the ease that comes from being strangers in a place where everyone is a stranger. He was from the area. He knew everyone. He took us to dinner and to his bar and then, the next day, an hour up into the hills to the village he grew up in.

We canceled our onward ticket and let the boat leave without us. We saw the town, and then a good deal more than the town, through someone else’s eyes, which is the only way to really see a place. What should have been a transit stop is still the part of Laos we talk about most.

That day did not end the way it started, and it changed how we think about the whole trip. We wrote about it properly here: The River That Gave and Took.

Vieng, if you ever read this: thank you.

Luang Prabang — 12 days

Honest answer: Luang Prabang didn’t land for us the way it seems to land for everyone else.

It is objectively beautiful. It sits on a peninsula between two rivers, its streets lined with French colonial architecture and saffron-robed monks and temples that glow in the evening light. Every morning the monks walk in procession through the town at dawn for the alms-giving ceremony, tak bat, and if you witness it with the quiet it deserves, it will stay with you.

We stayed 12 days, and that was a few too many. We weren’t there because we couldn’t pull ourselves away. We were getting over a cold and waiting on our next visa, and those two things together turned a stop into a stay.

We made it a good one anyway. We rented a scooter and rode out to the waterfalls. We climbed Phu Si hill at sunset. We ate laap and sticky rice and drank Beer Lao on slow evenings by the water.

Worth saying plainly in a guide like this: not every famous place is going to be your place, and that isn’t a failure on anyone’s part.

The Laos order: laap, sticky rice, repeat.

Then we got on a 27-hour bus to Vietnam.

That bus was an entire experience of its own, and we’ve written it up properly in our Southeast Asia budget guide. Short version: a mountain range, a border at dawn, and a fraction of the cost of flying. We’d do it again.

Vietnam

Hanoi — first stay, 5 days

Hanoi arrives loudly. The air is heavy and the whole town is whizzing. After the gentleness of Laos, the capital of Vietnam is a city that insists on itself: motorbikes moving in every direction at once, sidewalks that function as parking lots and restaurants simultaneously, a street food culture so good and so cheap it becomes difficult to eat anywhere indoors.

We spent five days getting our bearings, eating bun cha and pho and egg coffee, wandering Hoan Kiem Lake in the early morning, and preparing for what came next.

We also found a bánh mì shop under a big yellow tree and went back three times. On the last visit they waved us behind the counter, unstacked two extra stools, and handed us cold beers while we waited. That one got its own essay: A Plastic Stool in Hanoi.

The Old Quarter at night: lanterns, stools, and the best sandwich in the city.

The Ha Giang Loop — the highlight of the trip

We took a bus from Hanoi to Vi Xuyen (Thuan Hoa), near the Chinese border in far northern Vietnam, and rented motorbikes for four days on the Ha Giang Loop.

We want to be careful here not to over-describe it, because some things lose something in description. But we’ll try.

The Ha Giang Loop is a circuit through some of the most dramatic mountain scenery in Southeast Asia: limestone karsts rising straight from the valley floors, rice terraces cut into steep hillsides, passes that put you above the clouds and below them alternately as you ride. The roads are narrow and winding and occasionally terrifying. The villages are small and the people are Hmong and Tay and Lo Lo. You ride through places that still feel remote in a world that has very few remote places left.

We rode for four days. We got lost twice and didn’t mind. We pushed our bikes up a hill we weren’t ready for. We stopped at a viewpoint and sat there longer than we meant to because neither of us wanted to be the one to say we should keep moving.

And we met Daniel and Serena.

It was just the four of us on the tour, which is a good part of why it worked. We rode together, ate together, and stayed up later than any of us had planned. By the end we knew we’d made friends we hadn’t gone looking for.

They’re from Switzerland. They’re still some of our closest friends. We’ve stayed with them there, and they’ve come to visit us twice since this trip. None of that was visible yet from a mountain road in northern Vietnam, but we’d end these eight months on their couch.

Ha Long Bay — and the best doctor’s visit we’ve ever had

We didn’t go back to Hanoi after the loop. We went to Ha Long Bay.

Which is where Jesse got sick, and where we had our first experience with medical care abroad.

We had braced for the version everyone warns you about. We got the opposite. It was the fastest, cheapest, most efficient doctor’s visit either of us has ever had, in any country, our own included.

A translator was assigned to us the moment we walked in. We were taken straight to the right doctor and seen right away: two doctors and our translator, results reviewed on the spot. No waiting room. No paperwork gauntlet. No billing department. We paid, walked across the street with the prescriptions, and had them filled.

Start to finish, under 45 minutes and about $50.

We’re not claiming that’s what you’ll get everywhere in the region. But if part of what’s keeping you home is the fear of getting sick somewhere foreign, it’s worth knowing that the system we were most nervous about is the one that has treated us best.

Ninh Binh — 5 days (and Jesse’s birthday)

We went to the Ninh Binh region next, a landscape sometimes called “Ha Long Bay on land,” with limestone karsts rising from rice paddies and river valleys. We took a rowboat through the caves at Trang An and watched herons land in the fields outside our guesthouse window.

Jesse’s birthday fell here, and we spent it climbing. We hiked to the top of a mountain at Hoa Lư, in Ninh Nhất, for a view that made every step of it make sense: karst towers, paddies, river, the whole valley laid out underneath. Not a bad way to turn a year older.

Hoi An — TET

We timed it right and arrived in Hoi An for TET, the Vietnamese Lunar New Year, the most important celebration in the Vietnamese calendar. Hoi An during TET is something specific: the old town draped in red and gold lanterns, the streets transformed, families reuniting, the whole city lit differently.

We spent a week there, eating cao lau and white rose dumplings, making our own lanterns, taking a coffee class, and sitting along the Thu Bon River in the evenings watching lanterns float downstream.

Nha Trang — 4 days

A beach city on a wide, beautiful bay. This is where you rent a scooter and drive the coastal road for an afternoon just because you can.

We went to the Po Nagar towers, which have been standing there since long before the city grew up around them, and then to the Thap Ba mud baths, which is exactly as good an idea as it sounds after a few months of buses.

Da Lat — 5 days

Cooler, up in the hills, with French colonial architecture, strawberry farms, and a persistent drizzle we eventually made peace with.

Da Lat is where we had our first hot pot, and we have thought about it regularly ever since. We also spent a day out in the mountains with the waterfalls, which was the most fun either of us had on a day we hadn’t planned.

Ho Chi Minh City — 1 week

The energy is different from Hanoi. Faster, more modern, less ancient-feeling and just as overwhelming.

Daniel and Serena were passing through, so we met back up with them. Night markets, hookah bars, and the glass skywalk, which is a strange thing to stand on and worth doing anyway. We got tattoos, which we had not planned and do not regret.

We also visited the War Remnants Museum, which is not an easy afternoon but is a necessary one.

The Mekong Delta — 3 days

The four of us carried on together into the Mekong Delta, a maze of river channels and floating markets and villages where life still runs along the water.

We booked nothing in advance. What we did instead was take a last-minute local river tour with a guy named Thomas, and that turned into the entire day. He took us to a rice paper farm. Then we talked him into running us out to the river market, which was on no itinerary anywhere. We drove around for hours. It ended with all of us sitting on the roof of his wife’s pineapple boat, eating fresh pineapple.

You can’t book a day like that. You can only leave room for it.

We said goodbye to Daniel and Serena assuming it would be a while. We were wrong about that in the best way.

Phu Quoc — 3 days

A ferry to Phu Quoc, an island in the Gulf of Thailand near the Cambodian border. We’d planned on three slow days and ended up busier than that.

One day went to Starfish Beach. Another started early, riding through morning traffic all the way to the far side of the island to Sunset Town, then taking the gondola out across the water to the amusement park. That ride is long enough that it stops being transport and becomes the thing itself.

Cambodia

Sihanoukville & Koh Rong

We took a van from Phu Quoc into Cambodia, arriving in Sihanoukville for one night before catching a ferry the next day to Koh Rong.

Koh Rong gives you two options, essentially: a backpacker side and a luxury side. We picked the cheaper one, and we suspect that’s most of why we only lasted a night. It skewed younger and louder than what we wanted right then, which is a perfectly reasonable thing for a beach island to be. It just wasn’t ours.

So we went back to Sihanoukville, to the hotel we’d stopped at on the way through: Onederz. That ended up being the best part of Cambodia for us. You never had to leave for anything, which suited us fine, because we weren’t especially trying to. The food and drinks were good, the staff were great, the place itself was nice, and the pool was perfect.

We extended two more nights purely because of it. Sometimes that’s the whole story. You find somewhere that gets the details right and you don’t need another reason.

Back through Bangkok

A bus back into Bangkok for a week. We had suits made, something we’d been planning since Chiang Mai and finally had the timeline to do properly. Bangkok’s tailors are excellent and the process, if you have the time, is worth it entirely. We walked out with clothes that fit in a way off-the-rack never quite manages.

Southern Thailand

Phuket & Krabi

A flight into Kathu, Phuket, for five days on an island we’d heard polarizing things about. Phuket is big enough to be several places at once: yes, there is the strip of Patong and the roar of tourist infrastructure, but there are also quieter beaches and better food than its reputation suggests if you know where to look.

A ferry from Phuket to Ao Nang, Krabi, for four days. Krabi is spectacular in a way that photographs still somehow undersell. The limestone cliffs dropping straight into green water, the longtail boats at sunrise, the beach at Railay that you can only reach by sea. We kayaked, we hiked, we ate too much seafood. We were sad to leave.

Malaysia & Singapore

Kuala Lumpur, Penang & Singapore

A flight into Kuala Lumpur for four days. KL is a great city: cosmopolitan, food-obsessed, the kind of place where you can eat your way through a dozen different culinary traditions without trying very hard.

A ferry to Penang (George Town) for three days. George Town might be our favorite city in Malaysia. UNESCO-listed for its historic architecture, covered in street art that somehow manages not to feel forced, home to one of the best food cultures in a country already renowned for its food. We ate char kway teow and asam laksa and cendol and wished we had more time.

Two more days back in KL before flying to Singapore for two days, which is not enough time for Singapore, frankly, but enough to eat at hawker centres, walk the colonial district, and feel the order and ambition of a city-state that decided to take everything seriously.

The Philippines

Manila, Bohol, Cebu & Palawan

The Philippines felt like a reset. After weeks of mainland and peninsula travel, we were suddenly on islands again: a different light, a different pace, a warmth in the people that we noticed immediately.

Four days in Manila. Three days in Bohol, where the Chocolate Hills rise in hundreds of identical mounds from the flat land and tarsiers cling to branches in the dark with their enormous eyes. Four days in Cebu, where we did the canyoneering in Kawasan Falls, which involves jumping off cliffs into turquoise water and swimming through canyons and is one of the most purely fun things we did in eight months.

Then Palawan. Puerto Princesa for a few days, the Underground River, then the long road north to Port Barton: four days in a village so small it barely registers on most maps, with a beach that justifies the journey entirely.

El Nido & the four-day boat

El Nido is the kind of place that travel writing reaches for superlatives and runs out. The lagoons, the limestone karsts, the water that really is that color. We spent three days there and then boarded a boat.

The four-day journey north through the Palawan archipelago is slow and occasionally uncomfortable and completely worth it. You sleep on the boat. You wake up to different islands. You eat simple meals on deck and swim at stops and watch the stars in a way you can’t on land.

By the time we reached Manila we felt like different people than the ones who boarded, which is a thing a good journey does to you.

Indonesia

Bali & Nusa Lembongan

We flew from Manila to Denpasar, Bali, arriving in the late afternoon and catching the ferry to Nusa Lembongan the next morning. Lembongan is a small island southeast of Bali, car-free and quieter, with mangroves and surf breaks and a pace that Bali itself has largely outgrown.

We stayed six days. We rented scooters and circled the island in an afternoon. We watched surfers from a cliff. We ate at Sapir Kecia so many times that the woman running it knew our order, and we would eat there right now if we could.

We also got invited to a birthday party by the guys at the dive shop next door, which turned into one of the best nights of the entire eight months. That one has its own essay: Human Connection Across Cultures.

On our last night on Lembongan we met the Canadian family who would keep turning up for the rest of the trip.

The coastline that made us cancel the ferry twice.

Warung lunch, Nusa Lembongan. The bill came to almost nothing.

Lombok & Senggigi

A boat to Senggigi on the island of Lombok for 11 days, our longest stop in Indonesia. Lombok sits in Bali’s shadow in the tourist imagination but has its own complete identity: the rice paddies of the central highlands, the volcanic peak of Rinjani, the Sasak culture distinct from Bali’s Hindu traditions. Senggigi is relaxed in a way that suited us after months of moving.

We settled. We cooked some meals. We made tentative friends with a cat that lived near our guesthouse. We needed that.

Lombok is also where we found our favorite hotel of the whole trip. Eight months in, it was exactly the thing we needed and hadn’t known to look for: the holiday inside the trip.

Komodo & the islands

Two nights in Flores before the Komodo boat trip, which runs three days through the islands: Komodo Island and the dragons that move through the scrub in a way that makes you very aware that they are large predators; Pink Beach, which is genuinely pink from the coral; Padar Island at sunrise from a hilltop with the three bays below.

Nobody warns you how beautiful the sailing itself is. The islands sliding past between the stops, the water changing color through the day, everything happening at boat speed. That was half of what made it good.

Our Canadian family were on this boat too, which was becoming a pattern by then.

Gili Air — 4 days

The smallest of the three Gili Islands. No motorized vehicles, quiet enough that you can hear the ocean from anywhere on it.

After eight months of buses and boats and border crossings, Gili Air was the right way to finish. Calm and slow and unremarkable, in the best sense of that word.

Back to Bali — and the end

Two nights in Bali, at the same hotel we’d stayed in on our first night, eight months earlier. We hadn’t planned that. It landed harder than we expected it to.

Our Canadian family met us there, and we had one more breakfast together.

Then we sat on the beach and tried to account for the whole thing, which is impossible to do and also a good way to spend an afternoon.

The last evenings.

Then we flew to Switzerland.

Switzerland — the full circle

Daniel and Serena had been tracking us loosely through the months since the Ha Giang Loop. When we mentioned we were finishing, they said: come stay with us.

We spent 23 days in Switzerland. We hiked in the Alps and ate cheese and drank wine and slept in a real bed that didn’t move and cooked dinner in an actual kitchen. We talked for hours about what it had been. All of it, the slow boat and the hospital in Ha Long Bay and the four-day boat through the Philippines and the things we hadn’t expected to feel.

It was the right way to close something. With people who understood the kind of trip it had been, in a place completely unlike anywhere we’d been, letting the eight months settle into us before we had to figure out what came next.

What eight months in Southeast Asia taught us

We’ve had a lot of time to think about what the trip actually gave us, beyond the places themselves. Here’s what feels true:

The itinerary will be wrong, and that’s the whole point. We rerouted constantly: canceled tickets, extended stays, added countries. The best things that happened were not planned. Vieng in Pakbeng. Daniel and Serena on a mountainside in Vietnam. The hotel in Sihanoukville we’d never have found if we hadn’t turned around. Build in space for the thing you can’t schedule.

Slow down more than you think you need to. Twelve days in Luang Prabang. Eleven in Senggigi. A week in Pai. The places that became ours were the ones we stayed in long enough to stop being tourists in them. The temptation to cover more ground is always there and almost always wrong.

Something will go wrong, and it’s still not a reason to stay home. Jesse got sick in Ha Long Bay and we ended up in a hospital in a country we’d been in for a matter of weeks. It turned out to be the best medical care either of us has ever received, and it cost fifty dollars. That is not the story we expected to be telling. Get good travel insurance anyway, have a rough plan, and trust that you’ll figure it out, because you will.

The people are the trip. The landscapes in northern Vietnam are extraordinary. The temples in Luang Prabang are extraordinary. But what surfaces when someone asks us about the trip is almost always a person. Vieng, who let us cancel a boat ticket and drove us up to the village he grew up in. Daniel and Serena, who we met because four people happened to book the same tour, and who we now get on planes to go see. Thomas, who drove us around the Mekong Delta for hours and ended the day feeding us pineapple on the roof of his wife’s boat. The woman at Sapir Kecia who knew our order by the third visit. The Canadian family we met on our last night on one island and had breakfast with on our last morning in the country. Pay attention to people.

Eight months is both a long time and not enough. We came home with a list of places we want to go back to longer than the list we started with. That feels right.

How to Plan a Trip Without Overplanning It

Mon, 21 Apr 2025 00:00:00 +0000

There’s a version of trip planning that feels productive but quietly ruins the trip before it starts.

You know the one. The color-coded spreadsheet. The hourly itinerary. The ranked list of restaurants with backup options for each. Every museum pre-booked, every transfer timed to the minute, every day accounted for so thoroughly that the only thing left to do is execute the plan you made three months ago from your living room.

It feels responsible. It feels like you’re maximizing the trip. What it actually does is turn travel into logistics management, and close the door on everything that wasn’t already on the list.

The best things that have ever happened to us on the road were not on the list.

THE DAY WE MISSED THE BOAT

Somewhere on a slow river in northern Laos, we had a plan. A boat to catch. A schedule moving us forward through the region. Two people who had learned, over years of van life and slow travel, that the itinerary is a suggestion, but who still, occasionally, had to be reminded of that.

At the dock in Pakbeng, we met Vieng. He ran our guesthouse, spoke warmly and directly, and by the end of the evening had offered us something we hadn’t planned for: a day in his home village, an hour up into the hills. He wanted to show us where he grew up.

We looked at our schedule. We looked at each other.

We missed the boat.

What followed was one of the most genuine days of our entire eight months in Asia. His mother made lunch for the four of us, a careful, simple meal we still talk about. The village children went wild over the candy Vieng had suggested we bring. After lunch, the townspeople gathered. Rice wine appeared. More laughter than the language barrier should have allowed. Hours passed without anyone checking the time.

It did not stay that way. The last hours of that day took a turn we were not prepared for, and it’s the piece of the trip we’ve thought about most since. Karlee wrote the whole of it here: The River That Gave and Took.

None of that was in the plan. All of it is what we remember.

THE DIFFERENCE BETWEEN A FRAMEWORK AND AN ITINERARY

This is the distinction that changed how we travel, and it’s worth sitting with.

An itinerary tells you where you’ll be and what you’ll do at every point in the trip. It’s a schedule. It has the efficiency of a project plan and the flexibility of one too, which is to say, not much.

A framework is different. A framework says: here are the places I want to move through, here’s roughly how long I have, here are the two or three things I genuinely don’t want to miss. Everything else is open.

The framework gives you direction without giving you a script. You know you’re heading north. You know you want to spend time near water. Beyond that, you’re available.

Available to stay an extra two days because the place surprised you. Available to say yes when a stranger at a guesthouse invites you somewhere unexpected.

Eight years of van life taught us this before Southeast Asia confirmed it. We drove 48 states without a fixed route. The days that stand out from those years are almost never the ones we planned.

WHAT OVERPLANNING ACTUALLY COSTS YOU

We live in an age of immediate gratification. Everything is optimized, reviewed, ranked, and pre-decided before we even arrive somewhere. The phone is always in our hand. The next photo is already being composed before we’ve finished experiencing the moment we’re in.

Travel can fall into the same trap. When every hour is accounted for, your mind is always slightly ahead of where your body is. You’re at the temple thinking about the restaurant. You’re at the restaurant scrolling for the next day’s activities. You’re never quite where you are.

And when your week is locked, you can’t say yes to the things that don’t fit the schedule.

The best invitations arrive without warning. Vieng didn’t appear in any itinerary. The woman in Paris who took Karlee by the hand and walked her to someone who could help wasn’t on any list. The extra two days in Glacier because it was just that good weren’t planned.

The overplanned trip doesn’t just cost you presence. It costs you the trip itself. Travel isn’t a checklist of experiences to acquire. It’s a state of being available to the place, to the people, to whatever the day actually brings.

The hardest part isn’t planning less. It’s trusting that what shows up will be worth it.

It always has been for us.

HOW WE ACTUALLY PLAN

Book the first night only. Arriving somewhere new without accommodation sorted creates anxiety, not adventure. Book one night in advance so you can land without stress. After that, decide in person.

Identify your anchors. Every trip has two or three things we genuinely don’t want to miss. We book those in advance if they require it. Everything else stays open.

Build in nothing days. Deliberately. Not as overflow time or catch-up days, but as actual planned space. A day with no agenda is not a wasted day. It’s often where the trip happens.

Stay longer, go fewer places. Two weeks in three places beats two weeks in ten. You stop being a tourist and start being a temporary local. Vieng wouldn’t have found us if we’d been rushing through.

Give yourself permission to change the plan. Not just intellectually. Actually. The itinerary is not a commitment. The boat is not the only boat.

THE QUESTION WORTH ASKING BEFORE YOU PLAN

Before you open the spreadsheet or start building the day-by-day, ask yourself one question: what do I actually want to feel on this trip?

If the answer is present, unhurried, and open, then plan accordingly. Give yourself room. Build the framework and leave the rest to the road.

“I’m a big believer in winging it. I’m a big believer that you’re never going to find the perfect travel experience or the perfect meal without a constant willingness to experience a bad one. Letting the happy accident happen is what a lot of vacation itineraries miss.” — Anthony Bourdain

That’s not a travel style reserved for television hosts. It’s a decision available to anyone willing to hold the plan loosely enough that the trip can actually happen.

The road is better at this than you are. It has been doing it longer, and it knows things your spreadsheet doesn’t.

Vieng knew things your spreadsheet doesn’t.

Miss the boat occasionally. It’s usually worth it.

Why Shoulder Season Is the Smartest Way to See Europe

Mon, 07 Apr 2025 00:00:00 +0000

My first time in Paris, I was lost.

Not metaphorically. Actually lost, backpack digging into my shoulders, my friend equally exhausted beside me, both of us trying to find our hostel after a day of travel that had taken everything we had. Tired past the point where anything charms you. You just want to put something down.

We had been walking a while. We were clearly not where we were supposed to be.

A woman approached us. She was older, unhurried, put-together in the way certain French women are put-together: long fur coat, strands of pearls. She looked at us the way someone looks at people who are obviously lost and have stopped pretending otherwise.

I tried to ask for directions. We didn’t share a language. That became apparent quickly.

She took me by the hand anyway.

No negotiation, no hesitation. She walked us an entire block to a friend of hers, and the two of them worked together to figure out where we needed to go and get us pointed in the right direction.

I’ve thought about that woman many times since, and less about the kindness itself than about what made it possible. She wasn’t rushing between a tourist landmark and a restaurant with a queue out the door. She had time and attention. She noticed us, and she had the space to do something about it.

That’s what a city feels like when it isn’t overwhelmed.

Europe is expensive. We flew into Geneva last year with eight months of Southeast Asia behind us, and the contrast hit immediately: $2 bowls of noodles on plastic stools one week, a $22 sandwich in an airport café the next.

But when you go matters almost as much as where. Travel Europe in July or August and you’re paying peak prices for a diminished experience: crowds at every landmark, heat you didn’t plan for, restaurants running tired menus because turnover is guaranteed and effort is optional. The Trevi Fountain so packed you can’t see it from the street. Venice so full of day-trippers that locals have largely stopped coming to the center.

Travel in May or September and you get the same continent for a lot less money, with room to breathe, locals who are present, and the city showing you something closer to its real self.

For most of Europe, the shoulder months are just the better trip.

WHAT SHOULDER SEASON ACTUALLY MEANS

Shoulder season in Europe runs twice a year: late April through early June, and again from September through October. These windows sit between the summer crush and the winter slowdown: warm enough to enjoy, quiet enough to matter.

July and August are peak. That’s when school is out across Europe and North America simultaneously, when the queues stretch into the street, when accommodation can run 50–100% higher than shoulder rates. Flights follow the same curve.

November through March is off-season: cheaper still, but with shorter days, closed seasonal businesses, and weather that limits what you can do.

Shoulder season is the sweet spot.

THE SAVINGS ARE REAL

Airfare to Europe during shoulder season runs about 37% lower than peak summer months on average. Spain in particular delivers some of the steepest drops: flights nearly 47% cheaper compared to peak summer.

On accommodation, average nightly rates in cities like Paris and Reykjavik drop 30% or more. In Rome, savings on nightly rates can reach 40%.

Car rental prices can drop 30–50% during shoulder season. In places like the Algarve or Tuscany, that’s potentially hundreds saved on a week-long rental alone.

Add it together and travelers typically save 20–40% across flights, hotels, and attractions compared to peak season. On a two-week trip for two people, that’s often enough to cover an extra few nights, a nicer dinner, or the day trip you’d have skipped otherwise.

THE EXPERIENCE IS BETTER TOO

This is what surprises people.

The financial case for shoulder season is easy to make. The experiential case is the one that actually converts people, because what you get matters more than what you save.

Jesse traveled through Ireland, Greece, Belgium, Germany, Poland, Austria, and Switzerland, much of it outside peak season. He still talks about an afternoon in an Irish pub in early autumn, an afternoon that couldn’t have happened in July, when every stool is taken and the energy is performative. In Kraków, the Old Town square at dusk in September: unhurried, locals actually present, room to look up at the architecture without someone else in your eyeline.

And that Paris woman in the fur coat and pearls? That moment doesn’t happen in August. In August, she’s inside, windows closed against the tourist noise, waiting for September.

Shoulder season gives you the locals, and it gives you the city while it’s living its own life instead of performing for cameras.

WHERE TO GO AND WHEN

Not all of Europe behaves the same way seasonally. By region:

Mediterranean Europe — Italy, Spain, France, Greece, Croatia The most crowd-sensitive destinations on the continent. Spring or autumn brings reduced costs and calmer experiences. Best windows: May and late September through October.

Central Europe — Switzerland, Austria, Germany, Czech Republic By May and June, Central Europe is at its best: comfortable temperatures, tourist pressure not yet peaked. Best windows: May through early June, and September.

Western Europe — France, Netherlands, Belgium Paris is Paris year-round, but the experience shifts noticeably outside July and August. Spring and early autumn suit these cities far better than midsummer. Best windows: April through May, and September through October.

Eastern Europe — Poland, Balkans Already more affordable than the west. Shoulder season compounds those savings. Best windows: May and September through October.

One honest note: the UK and Ireland are wetter in October. Northern Scandinavia in April still has cold, short days. Check what’s actually running in your specific destination before locking in dates.

THE PRACTICAL MOVES

Book flights midweek. Wednesdays tend to be the best days for cheaper international flights; a midweek departure to Europe can save around 10% compared to flying on a Friday.

Set price alerts early. Use Skyscanner or Going to track fares across a flexible date window. Shoulder season deals move fast, and the earlier you’re watching, the better positioned you are.

Don’t anchor to one date. A one or two day shift in departure can mean hundreds of dollars in savings. Build the flexibility into your planning before you commit.

Book accommodation weekly when staying put. Boutique guesthouses and apartments in Europe often offer substantial weekly discounts. Just ask.

Shoulder season doesn’t mean cold. Southern Europe in September is warm and golden. Paris in May is one of the finest versions of Paris. Pack a layer and don’t let calendar assumptions talk you out of good weather.

THE HONEST BOTTOM LINE

Most people book Europe in July or August because that’s when everyone else does: school schedules, habit, the assumption that summer is when you travel.

That assumption is costing them money and experience at the same time.

Shoulder season doesn’t ask you to sacrifice anything, just to shift five or six weeks in either direction. The Colosseum is still there in September, the Seine in May. The Alps don’t pack up when August ends.

Everything is just quieter, cheaper, and in most ways better.

And somewhere in Paris, a woman in a fur coat and pearls might take you by the hand.

Our Exact 10-Day Travel Budget Breakdown (With Real Numbers)

Mon, 31 Mar 2025 00:00:00 +0000

Here’s something most travel blogs won’t tell you upfront: Southeast Asia is cheaper than your monthly car payment.

We know because we lived it. Eight months across Thailand, Vietnam, Cambodia, Malaysia, Singapore, Indonesia, the Philippines, and Laos, and by the time we did the honest math, the trip cost less than staying home would have. That’s not a sales pitch. It’s just geography, and a willingness to look at the actual numbers before assuming you can’t afford it.

So here they are. Real numbers. Current figures. A genuine 10-day breakdown for two people traveling Southeast Asia in 2025, the way we travel. Not luxury, not rock-bottom suffer-mode. Comfortable, immersive, real.

FIRST, THE CONTEXT

We’re not backpackers in the 22-years-old-sleeping-in-dorms sense. We want private rooms. We want to eat well. We want the occasional cold beer without counting every baht. We travel slowly, fewer places and more time, which almost always costs less than rushing between destinations.

This breakdown reflects that style. If you’re happy with dorm beds and street food only, subtract 20–30%. If you want boutique hotels and nightly restaurant dinners, add 40–50%. The framework stays the same either way.

For this breakdown, we’re anchoring in Thailand and Vietnam, two countries we know well, with some Laos context for comparison. Prices are in USD and reflect current 2025–2026 conditions.

THE DAILY BREAKDOWN: TWO PEOPLE, 10 DAYS

Accommodation — $25–$45/night total

Private rooms in family-run guesthouses run $15–$30 a night across most of Thailand and Vietnam. In Laos, you can find clean, comfortable rooms for even less. In Chiang Mai, we regularly stayed in lovely spots for under $20 a night. In Hanoi and Hoi An, $25–$35 gets you something charming, sometimes with breakfast included.

Vietnam tends to run 20–30% cheaper than Thailand across most categories. Private rooms outside capital cities generally fall between $12–$25 a night.

Budget: $30/night average for two → $300 for 10 nights

Food — $25–$40/day for two

This is where Southeast Asia genuinely defies logic if you’re used to Western prices.

Street meals (pad thai, pho, bánh mì) run $1–$2 each. Sit-down restaurant mains land at $4–$8. We eat street food for most breakfasts and lunches, then allow ourselves a proper sit-down dinner most nights. Cold local beers (Singha in Thailand, Bia Hà Nội in Vietnam, BeerLao in Laos) run $1–$2 a bottle.

A real day of eating for two people (coffee, two street breakfasts, a proper lunch, dinner at a local restaurant, two beers each) comes in around $20–$30 without trying hard.

A $1.50 institution.

Budget: $30/day for two → $300 for 10 days

Local transport — $5–$15/day for two

Grab makes city transport inexpensive and scam-proof. Scooter rentals run $5–$8 per day if you’re comfortable riding, and they’re worth it. Between cities, sleeper buses and night trains run $10–$30 for long hauls, and an overnight bus means you’re saving a night of accommodation at the same time.

Budget: $10/day average for two → $100 for 10 days

Activities — $5–$20/day for two

Many of the best experiences in Southeast Asia are free or nearly free. Temples. Markets. Wandering. The things that stick with you rarely cost much. We budget deliberately for a few paid experiences (a cooking class, a boat tour, a guided trek) and spread them across the trip. Jungle trekking with a guide generally runs $30–$50 per day total. Temple entry, where it’s not free, is typically $1–$5.

Budget: $10/day average for two → $100 for 10 days

Buffer — visas, SIM cards, the unexpected

Visa fees, entrance fees, SIM cards, and small surprises add roughly $3–$6 per person per day when averaged across a trip. Vietnam’s e-visa runs around $25 per person. A local SIM costs $5–$10 for the trip. Factor in a small emergency cushion and you’re covered.

Budget: $100 flat for the trip for two

THE 10-DAY TOTAL

Category	Budget
Accommodation	$300
Food & Drink	$300
Local Transport	$100
Activities	$100
Buffer / Visas / SIM	$100
Total on the ground	$900

That’s $45 per person per day, all in.

Add international flights (budget $700–$1,100 per person return from the US depending on flexibility and timing) and a 10-day trip for two comes in somewhere between $2,500 and $3,200 total, flights included.

On flights: the difference between the low and high end of that range usually comes down to two things, timing and tools. We book 6–8 weeks out for the best combination of availability and price, and we use Skyscanner and Going to track fares and catch deals before they disappear. We put everything on our Capital One Venture X card and earn travel points on every dollar spent. Over a trip like this, the points add up to meaningful money toward the next one.

On travel insurance: it’s not in the table above because the cost varies, but don’t skip it. A basic policy for two people covering a 10-day international trip typically runs $50–$100. Given what a single medical evacuation or cancelled flight can cost, it’s the most rational line item in the entire budget.

WHAT MOVES THE NUMBER UP OR DOWN

Slower travel costs less. The biggest budget leak in Southeast Asia isn’t food or accommodation. It’s transportation between places. Every time you move cities, you spend. Stay longer in fewer spots and the daily average drops noticeably. This is the single most effective thing you can do for your budget, and it makes the trip better at the same time.

Islands cost more than the mainland. Popular Thai islands like Phuket, Koh Phi Phi, and Koh Samui can run 25–50% more than mainland prices. Factor this in if beach time is part of the plan.

Peak season adds cost. Costs can run up to 30% higher during peak season (December through February in Thailand). Shoulder season (March through May, September through October) offers the best combination of lower prices and manageable crowds.

Couples have a structural advantage. A double room typically costs only 10–20% more than a single, effectively cutting per-person accommodation costs nearly in half compared to solo travel.

THE HONEST COMPARISON

What we kept coming back to during those eight months was that the math wasn’t just favorable. It was almost embarrassing.

The cost of two people living and traveling through Southeast Asia for a month was comparable to, and sometimes less than, what two people spend on rent, groceries, and routine expenses in many American cities. Not a vacation splurge. A lifestyle that happened to cost less than the one we’d left behind.

We’re not saying it’s for everyone. We’re saying: run the actual numbers before you decide it’s out of reach.

The world is cheaper than most people assume. They just never check.

All prices reflect current 2025–2026 data and will vary based on travel style, season, and destination. We’ll be revisiting these numbers periodically to keep them current.

How We Save for Travel Without Putting Our Life on Hold

Mon, 17 Mar 2025 00:00:00 +0000

People tend to assume we have some financial advantage that made the van possible. A windfall. A remote tech salary. Rich parents. Something that explains it.

None of those are true.

What we had was a decision, and a slow, unglamorous system that made it stick.

We’re not going to tell you to cancel your Netflix or stop buying coffee. That advice is patronizing and it misses the point. What actually moved the needle for us was something less satisfying and more durable: we stopped treating travel as a reward we’d get to someday, and started treating it like a line item we paid every month.

Here’s how we actually did it.

WE GOT HONEST ABOUT WHAT WE WERE ALREADY SPENDING

Before we changed anything, we tracked every dollar for thirty days. Not to punish ourselves, just to see clearly.

What we found wasn’t dramatic. No single villain. Just a pattern of small, unconsidered spending that added up to a number we hadn’t consciously chosen. Subscriptions we’d forgotten about. Meals out that weren’t particularly enjoyable, just convenient. Purchases that felt like nothing in the moment.

We weren’t living extravagantly. We were living on autopilot.

Once we saw it written down, we didn’t need a budget guru to tell us what to cut. It was obvious. We made a few deliberate choices, redirected that money, and opened a separate account we literally named “Van Fund.”

Naming it mattered more than we expected. It stopped being abstract.

WE LOWERED OUR BASELINE, NOT JUST OUR SPENDING

This is the part most saving advice skips.

Cutting lattes doesn’t change your financial life. Restructuring your cost of living does.

When we moved into the van, our monthly overhead dropped sharply. Van payment, insurance, and gas (vehicle and home combined) ran us under $1,100 a month. Split two ways. That covered where we slept, how we got everywhere, and every mile we drove.

Prices have gone up since then, but the math still holds: it was less than most people pay for a one-bedroom apartment, and it came with the entire country as a backyard.

No rent. No utility bills. No lease anchoring us in place. The van wasn’t free (build costs, maintenance, the occasional repair) but the total was significantly less than what apartment living had cost us, and we were moving the whole time.

That gap between old overhead and new overhead became our savings rate. We didn’t have to be disciplined about it. It happened structurally.

We’re not saying everyone needs to live in a van. But if you want to travel seriously, look at your fixed costs before your discretionary ones. That’s where the real money is.

Dinner: a few dollars, a fire ring, nowhere else to be.

WE TREATED THE SE ASIA TRIP LIKE A FINANCIAL DECISION, NOT A FANTASY

By the time we were planning eight months across Southeast Asia, we’d already built the habit of running numbers before romanticizing.

Here’s what we knew going in: the cost of living in Southeast Asia (accommodation, food, transportation, daily life) was a fraction of what it cost us to live in the United States. In many places we stayed, we were spending less per day than a single dinner out back home would have cost.

That’s not a travel hack. It’s just how far a dollar goes there.

We calculated a realistic daily budget for the region, multiplied it across our timeline, added a buffer for flights and unexpected costs, and compared it to what staying home would have cost us over the same period. The gap was significant enough that the trip, in some ways, made more financial sense than not going.

That reframe, travel as financially rational rather than financially reckless, changed how we talked about it. And it changed how easy the saving felt, because we weren’t sacrificing toward something irresponsible. We were building toward something we’d actually costed out.

THE SYSTEM, SIMPLY

See clearly first. Track your spending for one month before changing anything. Don’t guess. Know.

Name the account. Open a dedicated savings account for the trip and give it a real name. “Travel Fund” beats “Savings Account #3” every time. Your brain responds to specificity.

Automate the contribution. Set a recurring transfer on payday, even if it’s small. Consistency beats size. A hundred dollars a month for a year is twelve hundred dollars you didn’t have before. That’s flights.

Look at your baseline. Cutting coffee is symbolic. Cutting a subscription you forgot you had, downsizing a car payment, finding a cheaper living situation, even temporarily. These move real numbers.

Run the actual numbers on the trip. Don’t estimate vaguely and hope. Look up real accommodation costs in the places you want to go. Real food prices. Real transportation. Southeast Asia is not expensive. Neither is much of Central America, Eastern Europe, or Mexico. Look it up before you rule it out.

THE SMALL THINGS THAT ACTUALLY ADD UP

We always keep certain staples on hand in the van — basics we know we’ll use no matter where we are. But beyond that, we shop the sales. I’ll go in with a plan and a list, and if I spot something good the minute I walk through the door, I’ll scrap the whole plan and build a meal around whatever the deal is. That flexibility, the same instinct that has us turning toward Montana when we’re already on the road, saves real money over time and usually leads to better meals anyway.

None of the habits below are revolutionary. But we do all of them consistently, and the cumulative effect is real.

Join every store membership wherever you are. Grocery store loyalty cards, wholesale clubs, local co-ops: wherever we’re shopping, we sign up. The discounts compound quickly when you’re on the road and shopping every few days. Same goes for gas: we look up loyalty apps in every region we travel through. A few cents per gallon sounds trivial until you’ve driven 40,000 miles.

Check the map before you fill up. Fuel prices vary more than most people realize, even within a few miles. The station one exit over is often noticeably cheaper. Thirty seconds on the map, every time.

Waste nothing. Living in a van with a small fridge changed how we grocery shop. We go every three to four days, buy what we’ll actually use, and cook most of our own meals on the road. We don’t stockpile. We don’t let things go bad. It’s not a sacrifice, just paying attention.

Book accommodation by the week or month, not the night. Nightly rates are the most expensive way to sleep somewhere. When we’re staying more than a few days, we always ask about weekly pricing. Most hosts offer it. The ask takes one sentence.

Use flexible flight dates. A one or two day shift in departure can save hundreds on international flights. Check prices across a full month calendar before you pick your date, not the other way around.

Travel shoulder season. The experience is often better and the price is always lower. Shifting just outside peak season is one of the most effective ways to stretch a travel budget without compromising anything.

ONE MORE THING

There’s a version of this conversation that never gets said out loud: sometimes the financial hesitation isn’t really about money. It’s about permission.

Permission to want this. Permission to prioritize it. Permission to believe it’s actually possible for someone like you.

We get it. We sat with that hesitation for a full year before we booked our first flight to Asia. We watched the account. We ran the numbers. We talked ourselves in and out of it dozens of times.

The numbers eventually became clear. But the decision to take them seriously came first.

Start there.

Travel in Your 30s, 40s & Beyond

Mon, 03 Mar 2025 00:00:00 +0000

Somewhere along the way, a story gets told about who travel is for.

It’s for the gap year, the post-graduation backpack, the semester abroad, the summer before real life begins.

It’s for before.

Before the mortgage and the relationship and the career and the kids, before everything that apparently makes movement irresponsible.

And then, eventually, it’s for after. After the career is built and the kids are raised and the money is finally saved. After you’ve earned it.

Which leaves the middle. Decades of it.

We get groomed for that deal early. Your most capable, most vibrant, most physically willing years belong to work, and if you spend them correctly you might come out the far end with enough money and enough health left over to go do the things you wanted to do at thirty. Nobody says it to you out loud. Everybody signs it anyway.

Those in-between years are not a waiting room. They are the most alive stretch most of us get, and they hold a lot more than earning potential.

We’ve been living inside the contradiction of that story for years. And we want to say clearly: it isn’t true.

What we were told, and what we found instead

We bought our van before van life had a hashtag. Before the Pinterest boards and the YouTube channels and the algorithmic feeds full of perfectly converted Sprinters with string lights and pour-over coffee. There was no roadmap for what we were doing: no community of thousands doing it alongside us, no influencers making it look achievable. We were figuring it out largely on our own, which meant the decision felt bigger and the uncertainty felt louder.

What we got instead was the quiet version of the question everyone was thinking: when are you going to settle down?

We chose to keep asking a different question: settle into what, exactly?

Eight years later, forty-eight states covered, eight months in Southeast Asia behind us, we can say with some authority that travel in your thirties and forties is not a consolation prize for people who didn’t do it when they were young. It is its own thing entirely. Different in texture and depth, different in what it offers and what it asks of you.

And in many ways, better.

What changes, honestly

We’re not going to pretend nothing changes. Things do.

Recovery takes longer. You care more about sleep than you used to. The idea of a twenty-seven-hour bus ride on mountain roads in northern Laos lands differently at thirty-five than it did at twenty-two. We did it anyway, and it remains one of the more formative experiences of our traveling lives.

Somewhere around hour nine of twenty-seven, northern Laos.

You have more responsibilities to account for. More people who depend on you, or who at least have opinions about your choices. The financial stakes feel higher because they often are.

Planning matters more. Spontaneity is still possible, but it requires a more intentional container. You can’t just vanish for three months without building the systems that allow it.

None of this is an argument against going. It’s an argument for going differently.

What gets better

Still going out. Just home earlier.

You know yourself better. That alone changes everything.

At twenty-two, travel is partly about finding out who you are. At thirty-five, you have a clearer sense of that, which means you can be more deliberate about what you’re looking for. You’re less likely to fill every hour because you’re afraid of missing something, and more likely to stay somewhere an extra week because the rhythm feels right.

You’re a better traveler in the practical sense too. You’ve made enough mistakes to have genuine judgment. You know what comfort you actually need versus what you thought you needed. You know how to move through friction without it ruining the day.

And perhaps most importantly: you have more to bring to the experience. The grandmother passing soup to her grandson in Hanoi lands differently when you’ve watched your own family age. The kindness of a stranger who stops on a back road in Utah because your van looks like it’s having a bad day means something different when you’ve been the stranger enough times to know what it costs to offer it.

Experience doesn’t diminish travel. It deepens it.

Travel in your thirties and forties isn’t the same as travel at twenty-two. It’s not supposed to be. It’s supposed to be its own thing, and it is.

The permission question

The most common thing we hear from people in their thirties and forties isn’t “I can’t afford it” or “I don’t have time.”

It’s “I feel like I should have figured this out by now.”

Like the window closed. Like movement was something you were supposed to get out of your system before life got serious, and if you didn’t, you missed it.

Karlee’s grandparents taught her the cost of that belief. They had the plan. The camper. The list of places they were going to see when the time was finally right. The time was never right. The trip never happened.

That story lives in a lot of families. It lives in a lot of people who are reading this right now.

You are not too old. You have not missed the window. The window is not a window. It’s a door, and it opens from the inside.

What this looks like practically

Travel in seasons rather than waiting for a permanent version of freedom
Build the financial structure first; freedom expands when the numbers are honest
Design for your actual energy, not the energy you had at twenty-two
Accept that some things cost more now, and that some of those costs are worth it
Stop measuring this version of adventure against a previous one
The skills you’ve built (patience, resourcefulness, discernment) make you a better traveler than you were before

Eight years in. Still going.

We’re not writing this from the other side of some finish line. We’re writing it from inside the doing of it, from a life that is still in motion, still being designed, still asking us to choose it again and again.

And we’re writing it because we spent too long wondering if we were allowed.

You are allowed.

The miles don’t check your age at the door. They just ask whether you’re willing to show up.

There is no age limit on curiosity.