How I planned our trip to Southeast Asia – step by step, with compromises

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For as long as I can remember, seeing the sunrise at Angkor Wat has been a dream of mine. This story starts the same way many of mine do: as a teenager, watching the History Channel, I never imagined I would actually make it happen one day. When it started to take shape that 2025 would be the year Ádi and I set off on this adventure, there was one thing I was certain about. If we were going to do it, we should do it properly — by visiting multiple countries in one trip. That’s how we ended up choosing Vietnam, Cambodia, and Thailand. But let’s not jump ahead just yet. How did the planning begin? How did we decide on the order of the countries? And how did I put our itinerary together? This article is about how I planned our trip to Southeast Asia — what step-by-step planning looked like for us, and what kinds of decisions we had to make along the way, including the compromises that came with them. I hope this is helpful if you’re considering doing something similar. I also believe this approach isn’t only relevant to this specific journey, but can be applied more generally to planning a trip that spans multiple countries.

I don’t think there is such a thing as one universal “first step” when it comes to travel planning. It depends heavily on the type of trip. Factors like complexity, distance, and certain constraints all play a role — especially those elements that are only minimally flexible, or not negotiable at all.

Entry requirements

Even though this wasn’t my very first step, I would absolutely recommend making it yours — because this is the point where one wrong piece of information can derail the entire trip. Luckily, we didn’t have any major issues, as I already had a rough idea of what to expect, and we still had plenty of time before departure. At this stage, you want to know exactly what you’ll need to enter the country: passport requirements, visas, and any additional documents. When it comes to visas, it’s important to look into both the process and the timeframe. Sometimes it’s just a few clicks online, and you’ll have it within a day or two; other times it’s more complicated and takes significantly longer. In many cases, the length of your stay also affects how the process works. Once you’ve checked everything and sorted it out, it’s still worth revisiting these requirements occasionally while you’re waiting for your trip — just to make sure nothing has changed. In our case, Vietnam actually abolished its visa requirement in the meantime, which worked out in our favor. But the opposite can also happen, and regulations may become stricter.

Timing & weather

These two factors are key for any trip, as the weather can either make or break the experience. Since I knew we would be traveling in October — a month when conditions can be quite unpredictable — we were prepared for pretty much anything. It’s also important to keep in mind that the weather isn’t necessarily consistent across an entire country at the same time. In practical terms, this can mean needing warmer layers in one place, while being greeted by humid heat somewhere else. This was especially true for Vietnam and Thailand, given their size and geographical diversity, but it was also something we had to factor in for Cambodia.

Route, transportation & costs

Temple of Literature

This was by far the hardest part to plan and decide on. One thing is how much flights cost, but what matters even more is how you can actually move between countries. Before anything fully took shape, I opened my laptop and went down several late-night research rabbit holes. There was a bit of everything involved — AI tools, Google searches, and whatever else I could get my hands on. What helped the most was reading relatively recent travel blog posts (from the past six to twelve months) written by people who had done something similar. I saved links, took notes, and gradually outlined a rough framework — nothing detailed yet, just the big picture. This helped me estimate how much time we could realistically spend in one or two countries, and what the overall length of the trip might look like. I searched for flights mainly using Google Flights and Skyscanner, and also checked a few airline websites directly. By this point, I had a couple of solid options: booking outbound and return flights separately, as well as a multicity setup (booking everything with one airline — flying from point A to B, then returning from point C back to A). After that, I looked into transportation options between destinations, both within individual countries and across borders. Since we didn’t have a full month for this trip, we combined cost-effective but time-consuming bus journeys with slightly more expensive — but much faster — flights. At this stage, I already had an Excel sheet where I tracked all the details. I also spent some time reading trip reports and reviews, just to make sure we wouldn’t run into major issues and that I wouldn’t have to redesign the entire plan later on. Not obsessively — but enough to feel confident about the choices we were making.

Sightseeing & points of interest

This entire trip started with Ádi asking me to present my idea to him. He didn’t mean it literally — but I did. Coming from a corporate environment, that part came quite naturally to me. So alongside my Excel sheet, I also ended up putting together a PowerPoint presentation. I’m a very visual person, and this helped me a lot when it came to imagining how the trip would actually look. I mapped out our route on a small map and started sketching out our days in a calendar — what we might do, and where we might go on each day. Because I had already done a lot of reading before getting into the finer details, the main cities and must-see sights were already on my radar. I also started collecting images of these places, mainly because I had trouble remembering all the names. At this stage, I looked into how much time each attraction would realistically require, whether certain sights could be combined, and whether it made more sense to join organized tours or handle everything independently. I won’t pretend there weren’t moments when I had gathered so much information that I felt completely overwhelmed and close to giving up. When that happened, I simply stopped researching, stepped away from the whole topic, and picked it up again the next day with a clearer head.

Royal Palace of Cambodia

At this stage of the planning process, I already had a rough itinerary, and it was time for the big presentation. There was plenty of laughter as I cleared my throat and fired up the PowerPoint. We spent a lot of time talking things through together — deciding what we absolutely wanted to see, where we could afford to scale things back a bit, and finally starting to seriously juggle our vacation days.

When it comes to travel planning, I think there has to be a point somewhere between the very first idea and actually starting to book things where you stop and ask yourself a few honest questions: What do we really want? What kind of trip are we looking for? What’s the main motivation behind it? And do our plans so far actually reflect that? For us, the answer was fairly simple: we wanted to see these three countries. We knew that within our limited timeframe — and with a condensed list of sights — a slow, relaxed, beach-heavy trip would be a bit of a naive illusion. Instead, we calibrated our expectations accordingly: this would be a fast-paced journey, with lots of moving around, long days, and not much sleep — but also one where we could see everything we truly wanted to see. Of course, we still made room for one or two days by the sea, and a last-minute diving trip even slipped into the plan. But all things considered, we knew this was exactly what we wanted to do at this point. We could have gone back to the drawing board and chosen something completely different — but we didn’t. This was the decision we made.

Finalizing the plan & bookings

Once we agreed on the overall itinerary, I started digging much deeper into the details. Where should we go, and when? What kind of weather could we expect, and could that cause any disruptions? Would we have enough time to rest? Were there any activities that needed to be booked in advance? This was the point where Koh Rong in Cambodia dropped out of the plan. The risk of having our beach time washed away by rain felt too high, and getting there would have been quite time-consuming and complicated anyway. So, as painful as it was, we decided to let it go.

The first thing I booked was accommodation. I found plenty of great deals on Booking.com, so I went ahead and secured them — all with free cancellation and no upfront payment. Looking back, that turned out to be a very good decision, as the best rooms sold out within weeks. We waited a bit longer before buying our flights. About three months before the trip, we booked a multicity option that included a longer layover in Doha on the way back. This wasn’t part of the original plan, but once we realized we would arrive home at the same time as we would have with a shorter, overnight connection, we decided to take advantage of it. In return, we got a hotel stay and even managed to do a bit of sightseeing.

After that, we booked the remaining pieces — meaning domestic flights and bus journeys. By this point, we were about three to four weeks away from departure, which meant it was time to start the visa application process and finalize programs as well. That part required some research and effort, but having read so much beforehand — and using AI as a supporting tool — made the whole process significantly easier. My goal was simple: by the time we left, everything should be in place, so that once we were there, only minimal organizing would be needed.

Travel insurance

Ha Long Bay

This is one thing you should never skip — and definitely not something worth saving money on. I usually arrange my travel insurance through an online comparison platform, but this time, largely due to the geopolitical situation, I took a closer look at what exactly was covered and what might be excluded. The key point is this: you don’t want to find yourself in trouble only to realize that your insurance doesn’t actually apply to the situation you’re in. In my opinion, this is something you can sort out one to two weeks before departure.

By the end of the planning process, I had an Excel sheet with a day-by-day itinerary, saved Google Maps with pinned sightseeing spots, and a checklist tracking when we needed to check in for upcoming flights and complete the required entry forms. I also saved our travel insurance details and the emergency contact number, just to make sure everything was easily accessible if needed.

All things considered, it was a lot of work and took up a huge amount of my time — but it was absolutely worth it. What would I do differently? I’d get less lost in the details at the beginning and put together a solid core itinerary sooner, so that the only things left would be fine-tuning programs and making bookings. I’d also try to add at least one or two extra days to the trip, simply to allow for a bit more rest.

That said, I’m genuinely happy to say there wasn’t a single experience we had to skip. The packed schedule paid off, as did all the time invested in planning — once we were there, everything ran smoothly, and if anything unexpected came up, we were able to handle it quickly and easily.

Conclusion

If there’s one thing I’ve learned from all of this, it’s that a great trip isn’t defined by how much you manage to fit in — but by knowing why you choose to leave certain things out. No matter how much you plan and prepare, you also have to be ready for the unexpected. As someone who can be quite control-oriented, I’ve learned this the hard way (and yes, I now build it into the plan — half-jokingly). Jokes aside, it’s important to keep a certain level of mental flexibility and openness, so that when unexpected situations arise, we don’t experience them purely as problems, but rather as part of the adventure — and focus on what we can make of them. Whether that’s a long-standing regional tension escalating shortly before your trip, or a major event that suddenly affects places you were planning to visit.

While writing this article, I also realized just how much there is to say about individual aspects of planning — like booking flights, or organizing and reserving activities — each of which could easily deserve a dedicated deep dive of its own.

More detailed stories are coming about the countries and cities we visited on this Southeast Asia trip. If you don’t want to miss them, make sure to subscribe to the newsletter. Until then…

Adventure awaits! 🌍

Thank you for reading!

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