How I Planned My Itinerary Through Southeast Asia

Itinerary planning is a complex beast. There’s no single best way to do it. Everyone has different travel desires, goals, and needs. It’s why I’ve always shied away from discussing itinerary planning beyond the most simple advice: don’t double back.

I don’t know what you want or like, so suggesting complex, multicity routes is something I generally can’t do.

But one thing you readers brought up a lot in the latest survey was itinerary planning. How do I do it? How do I figure out where to go? What’s my logic?

While there is no magic formula to creating an itinerary, I want to share with you how I pick the routes I take and my strategies for deciding which destinations get voted off the island.

Moreover, moving forward, I’ll write more posts like this (and I might even go back and tell you how I designed some of my previous itineraries) but, for now, let’s start with my current two-month jaunt around Southeast Asia.

The first thing to know about itinerary planning is that it is always going to disappoint you. Why? Because you’ll stare at a map and say “I want to go here, here, here, and definitely here,” then suddenly realize you won’t have enough time to see it all. Something will to have to get cut, and that’s going to make you sad.

And so come to terms with the fact you will be disappointed and you will miss something. You can’t see it all, so don’t try. Just enjoy as much as you can in the time you have. Don’t go too fast. Don’t rush to visit a million places in three weeks. Go at your own pace and experience as much as you can. It’s not how much you see, but how you see it.

Originally, I was planning to travel from Bangkok into Isaan, Thailand’s rural northeast province, for a couple of weeks then go to Pakse and the 4,000 Islands in Laos before heading up to Vientiane (with stops along the way) the back through of Isaan and finally into Bangkok. After that, it was to the Philippines. This would give me about six weeks in Southeast Asia and two weeks in the Philippines.

Here’s a map of the route:

It flows in a nice circle, there’s no doubling back, and it hits lots of major on- and off–the-beaten-path spots I’ve always wanted to see. This route really allowed me to hit a lot of spots at a reasonable pace. Mostly, the weeks were about visiting friends in Bangkok and seeing Isaan.

I’ve never really explored the heart of Isaan and have always felt that was a big gap in my Thailand exploration. It’s a very rural part of the country, famous for its landscape, food, and national parks. Since I would be close by, I decided to add in the 4,000 Islands in Laos. This popular area is famous for the river dolphins in the Mekong, chilled-out vibes, bungalows, and swimming — you come here to relax. Looping up to Vientiane allowed me to see rural Laos before heading back into Isaan and Bangkok. I didn’t know exactly where I would go but I’d follow this general direction, filling in the gaps along the way.

I might not make it to all of these destinations, but this plan gave me a good starting point and general direction to follow. (Though, if history is a guide, I’m prone to change where I go.)

However, just before I flew to Hong Kong, my friend Jodi called and said she was staying in Thailand longer than she’d planned — but she was in Chiang Mai, so in order to fly there to see her and my friend James, I had to revise my entire route. Where to now?

While I see less of Isaan, this route lets me see a host of new places. I picked Pai because I’ve never bee,n and it’s a hit with travelers. There’s also a cave there I want to see called Tham Lot. I plan to spend a few days there before heading into Chiang Rai on my way into Laos. Chiang Rai is a good stopping point (it’s near the border) before heading into Luang Prabang, a city renowned for its Buddhist temples. Then it’s off to the Plain of Jars and Vang Vieng, a city that was once ruined by backpackers who turned it into a drunken booze fest of stupidity. Luckily, the government put an end to that, and I want to see how the city’s changed now that people don’t get drunk and jump off something called “the death slide.” After that, it’s off to Vientiane before traveling to Isaan and into Pakse.

The last time I was in Laos, Bush was president, so it’s time to go back and really travel around the country with fresh eyes. I haven’t seen much of it, and, given all my time in the region, I need to change that.

And, as for the Philippines, well, I haven’t thought that far ahead.

Because who knows, I may not end up there at all; maybe I’ll get stuck somewhere along the way. My grand plan may all go out the window, but at least for the next week or so, I have a general idea as to where I’m going. When I plan routes, I leave a lot open in case plans change — and I don’t pre-book anything either. You never know if you’ll want to stay longer or leave sooner, so just book along the way!

As for researching the actual destinations, these days I don’t particularly do much research beforehand on places, as I find the best advice is usually available on the ground once you arrive. However, I did use Travelfish a lot as it’s the best resource for travel in Southeast Asia. Shout out to Stuart for answering the million questions I had about the region! For Pai, I read what Alex in Wanderland had to say since she’s a super fan of the city. However, for everything else, I haven’t bothered to look yet. After years of travel, I’m happy just winging it!

So that’s my current route through Southeast Asia and why I’ve picked the places I plan to visit.

I realize many of you were hoping for more elaborate plans and tips, but really, it’s as simple as picking where you want to go and how long you want to be there. I typically pick a general route and then just wing it. If I make it all the way, I make it all the way. If I change, I change. After all, the most important part of travel is being flexible!

P.P.S. If you’re going traveling soon, check out the newly expanded resource page. I added some more of my favorite companies and websites.