Last Updated: 7/10/20 | July 10th, 2020
Itinerary planning is a complex beast. There’s no single best route out there. Everyone has different travel desires, goals, and needs (let alone budget). It’s why I’ve always shied away from discussing itinerary planning for long-term travel beyond the most simple advice: don’t double back.
Showing someone how to plan a trip is one thing, but planning a trip for someone else is tricky because I don’t know what they want or like.
Because, at the end of the day, there is no magic formula for creating an itinerary. You have to see and go where you want to go and, while suggested routes can help inspire you, at the end of the day, only you can plan the best route for you.
Just don’t double back (it raises your costs a lot).
BUT, to help you get familiar with how to plan an itinerary, I want to share how I decide my routes. Or at least the general routes (because, often when you land in a place, you throw out your plans and let the wind take you).
To illustrate my points, I’ll use a semi-recent two-month jaunt around Southeast Asia.
Tip #1: Dreams vs Reality
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 (or money) to see it all. Something will have to get cut, and that’s going to make you sad.
So, the first thing you need to do is accept that you likely won’t be able to see and do everything — unless you’ve got unlimited time and a solid travel budget. You’ll still be able to see and do a ton of amazing things, so don’t get discouraged. Merely set some realistic expectations at the start.
Tip #2: Always Slow Down
I can’t stress this enough. All too often I see travelers plotting their dream trip and bouncing from one destination to another every 1-2 days.
That’s a terrible idea.
If you try to move between destinations every few days you’re just going to end up spending all your days in transit. Your trip will be a blur and, while you might have some nice photos for Instagram, you won’t remember a thing.
I traveled way to fast on my first trip to Europe. Most people do. The importance of slow travel is something we travelers usually learn the hard way.
Slow down. Take your time to soak in each destination. Travel is about quality, not quantity! Trust me. Less is more.
Tip #3: Be Flexible
As you can see, plans change. You meet people or learn about something new and all of a sudden your planning goes out the window. That’s why I always encourage travelers to have a suggested itinerary but build in enough room for flexibility. That way, if you need to make a last-minute change you can do so without stressing out.
When I plan my travel routes now, I leave much more room in case plans change — because they always do. And I don’t pre-book anything either (unless it’s a super busy time of the year). You never know if you’ll want to stay longer or leave sooner, so just book along the way. Sometimes I love a city and decide to say longer. Sometimes I dislike a place and leave sooner than expected.
Give yourself that wiggle room. That way, no matter what comes your way you’ll be able to adapt.
Real World Example: My Southeast Asia Itinerary
My Original Plan
Originally, I was planning to travel from Bangkok into Isaan, Thailand’s rural northeast province, for a couple of weeks.
Then, I’d go to Pakse and the 4,000 Islands in Laos before heading up to Vientiane (with stops along the way). Then, I’d go the back through Isaan to Bangkok.
After that, it was off to the Philippines. This would give me about six weeks in Southeast Asia and two weeks in the Philippines.
That itinerary packs in a ton of amazing things to see and do. But it also leaves no downtime, no time to sit back and enjoy serendipitous experiences. It’s an exhausting itinerary and one that requires a go-go-go mentality for weeks on end.
Yes, this travel route 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. But it’s not a reasonable pace.
Now, since I’ve been to many of these places before I don’t need as much time, which is why an itinerary like this can work. However, when visiting places for the first time, an itinerary this packed is going o be more exhausting than it is fun.
And it doesn’t leave room for flexibility — which is something that every traveler needs to embrace.
Why?
Well, 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. In order to see her, I had to revise my entire route on a whim.
My Plan: Version 2.0
In this revised version of my trip, I see less of Isaan. However, the route lets me visit a host of new places. I picked Pai because I’ve never been and it’s a hit with backpackers. I planned 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.
What I ACTUALLY Did
Even after creating multiple itineraries, what I did was still pretty different from my revised itinerary:
Bangkok – Chiang Mai – Pai – Chiang Mai – Luang Prabang – Vang Vieng – Vientiane – Bangkok – Korat – Nong Kong – Surin – Ubon Ratchathani – Pakse – Nong Khai – Khon Kaen – Bangkok
This final itinerary was super different from my original plan. I still explored Isaan but, because I went to Chiang Mai, ended up seeing a lot of Laos too. This itinerary ended up being a lot better than my original.
The point of all this is that your plans will change. Sometimes by a lot. Don’t be married to your plans and don’t say no to opportunities just because your “route” says no. Travel is best when you go with the flow.
Build extra space into your itineraries. Be flexible. Go slow.
That’s how you plan an amazing itinerary – not only to Southeast Asia but to anywhere in the world.
Book Your Trip to Southeast Asia: Logistical Tips and Tricks
Book Your Flight
Use Skyscanner or Momondo to find a cheap flight. They are my two favorite search engines because they search websites and airlines around the globe so you always know no stone is left unturned. Start with Skyscanner first though because they have the biggest reach!
Book Your Accommodation
You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:
- World Nomads (for everyone below 70)
- Insure My Trip (for those over 70)
- Medjet (for additional repatriation coverage)
Looking for the Best Companies to Save Money With?
Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.
Want More Information on Southeast Asia?
Be sure to visit our robust destination guide on Southeast Asia for even more planning tips!
Lindsay
If you go to Pakse – there is an island nearby on the Mekong called Don Daeng that is really lovely! I did a homestay there last year, the people are fantastic and the local kids play soccer on the beach every day at sunset. HIGHLY recommend!
NomadicMatt
That’s definitely on my list!
Lauren Meshkin
I really enjoyed this! Itinerary planning is one of my favorite things to do, other than traveling of course 😉 Also… “The first thing to know about itinerary planning is that it is always going to disappoint you.” SO TRUE! Haha, thanks Matt.
Happy travels 🙂
Allan
Please do visit the Philippines! Celebrating Christmas and New Year in the Philippines is highly recommended!
NomadicMatt
That’s the plan!
Martin
Where in the Philippines are you thinking of going? I spent about six months in Palawan, but would love to see more of the country!
Monelle Mondello
Hi there,
I’m planning to spend this Christmas and New Year solo in the Philippines and I’m mainly planning the trip around diving.. do you have any recommendations on how/where best to celebrate?
Thanks,
Monelle.
Nisha
Oh I change itinerary quite a lot. I am thinking of East Europe for 3 months, want to see places but not in a hurried way. I know I am not doing justice to places but I\’ll still go slow.
Sometimes to have a flexible route makes a difference. 🙂
Karen
One thing to keep in mind for new travelers is leaving enough time at 1 location. I personally think it’s good to schedule 2-4 days in each city. 2 days for a smaller one with few tourist sites, 4 days for a place that has a lot to see. That just gives you a general guideline on how to plan your route. If you try to do shorter visits than that, then you end up spending most of your time travelling.
Brooke
Yes, much agreed — and if you do decide to travel at a quicker pace, put some “down time” in your schedule! My husband and I often reach the second/third week of a trip and are totally wiped out, especially if we’re somewhere where we constanyl have to stay on top of logistics.
NomadicMatt
I too agree. Don’t speed when you travel!
Scott
Great advice! When I plan an itinerary I decide where I want to start my trip and where I want to end my trip. Usually every thing in the middle will just come together.
Jared
Looks like a fantastic trip Matt. Great to see you’re hitting some spots in Thailand that aren’t on the ‘traditional’ backpackers route.
If you end up getting to the Philippines (on my list as well – waiting for my Filipino wife to take me!), there are some amazing caves I’ve read about – I think largely concentrated north of Manila. Have also heard great things about Palawan.
Also, great advice on taking it slow. The biggest mistake I hear about when friends tell me of their travel plans is trying to hit every city, attraction etc in a short amount of time. Especially difficult for us Americans with limited number of vacation days, but you’ll come back with such a richer experience if you take it easy on the road.
Cheers,
Jared
Marjan
There are many ways to go about travel planning. I hear most do it like Matt. But, in order to further maximize the value (experience per $), I have a different approach. I am extremely opportunic. I plan to go where I find a deal that is just too good to pass. This often leads me to destinations that make people go \”you travelled where??\” But, I tell you, nearly any unfamiliar far away destination can be exciting. 😀
Here are some tips some might be able to benefit from.
1. Sometimes flying can be near free if buying tickets during \”super sales\”. Jump on them when an opportunity presents itself. Currently, I have over 10 AirAsia flights booked, at a cost of ~$100 total, for 2!
2. I plan many routes around unbelievable hotel deals. It can take a lot of research, knowledge, flexibility and advance commitment though. But, just as an example, last 2 months I (+gf) lived in 5* hotels around China nearly all-inclusively for $20 per night. I kid you not. And in the process I got to explore the country for peanats.
The best value is usually achieved when combining travel hacking mastery with (1) and (2).
How far you go with micro planning at various destination is then up to you. I tend to plan in-depth, often before even booking anything. This way I make sure I book a long enough stay and minimize the likelyhood of costly bad surprizes. Also, at times, researching what to do and where to go once at a destination, especially if a non-touristy one, can be extremely difficult. Internet issues, language barriers, locals (even 5* hotel concierges!) can be surprisingly clueless. And poor research/knowledge can easily lead to expensive experiences.
In any case, do what it suits your goals, skill level, personality, etc. Everybody is different. I know I am the weird one.
Travelling full time for 3 years now…
Bridgette
I definitely learned not to book everything in advance the hard way haha when I had 3 weeks in the US, I booked everything down to the very last detail, and I regretted it as soon as I got to New York and realised I wanted longer than my originally planned 4 days. I was rushing around trying to do everything I wanted to do and it was a mess. unfortunately I couldn’t change any of my plans, because it would have been way to expensive. well, at least I know for my next trip to do a lot less planning.
NomadicMatt
Some of the best lessons are sadly learned the hard way.
Jennifer
I’m a slow traveller – for example I’ve allowed 3 weeks to do Chiang Mai – Mae Hong Song – Chiang Rai. I like to have a general idea of where I’m going but not plan too many details, because awesome opportunities always pop up! Plus I enjoy having down time when I’m travelling – but maybe that is just me getting old! 😉
Sarah
I really enjoy the trip planning process although at times I go overboard and can research with no end in sight. I don’t like to create a day to day itinerary just have a general plan for things I would like to see and places to go. Enjoy Laos -one of my favorite countries I’ve visited!
Devon
I’m currently on country #39. For trips ten days and under, I like to start by looking at pictures. Once I’ve compiled a list with my eyes, then I take out a map and see where everything is in relation to each other. Of course some things will be cut and yes, you’ll be sad. I always leave one or two flex days to allow for surprises.
I’m on a round the world trip now and I don’t plan more than two weeks in advance. I keep key places and people in mind and let the rest of the trip plan itself. Already I’ve regretted squeezing too many countries into a short amount of time. Sure you gain bragging rights, but it all becomes a blur.
What’s more important the brag or the business of really knowing a place?
NomadicMatt
Never the brag!
Mailoha
Hi. I have traveled alone a lot in the past but I would like to travel with people now. Any tips on how to find people to travel with? Any good sites that do good group travel? I went on tourbar.com but all I get is creeps 🙁
NomadicMatt
You can meet plenty of people on the road but try Couchsurfing or the forums here!
Manu and Kasia
We’re currently exploring Laos and eventually heading to the 4000 Islands as well! 🙂
As for Vang Vieng – it’s a great place now! Even though the party didn’t die completely – you can still go tubing, but not that many people do that – it has a very chilled out vibe and makes for a great base to go jungle trekking.
If you have a couple of days there and want some off-the-path experience, you should definitely drop by LaLaLand bar – the guy that owns it was pretty much raised in the jungle and offers amazing guided tours to some hidden locations. They are a bit rough, but very memorable.
If you decide to take a secret waterfall trip, you’re up for for some hiking in pitch-dark caves (with bamboo torches), fighting with leeches and getting to amazing places seen by almost no other people 🙂 We’re already planning to come back there 🙂
NomadicMatt
Thanks for the tips!
Luke Mitchell
I love seeing how much this blog has changed from the beginning and how many places you have been and where you’ve gone in more ways than just physical locations. Travelling allows a person to grow so much, to gain insight and wisdom that cannot be gotten any other way. It’s great that you can change your plans on the fly and just decide to be somewhere else at a moment’s notice, it actually makes the entire experience that much more enjoyable.
NomadicMatt
Thanks for such an awesome compliment!
Victoria
A really honest article! We did a tour of Europe in 2014 and made an extensive pre travel itinerary, which as our first experience of travelling helped us be more organised. But whilst we were actually there, we found that quite a lot of our route and times changed depending on how we felt. It’s so useful to have a general idea of the route you want to take but to leave yourself time to explore and have some room for changes, you never know what you’re going to discover when you’re actually there!
One thing I wanted to ask you about SEA though is how did you get around the visa issue? We’re planning our next RTW trip to include SEA and have noticed the visas suggest it is likely you will need proof of onward travel (as in many places). Obviously if we book an onward flight in advance we are then limited and less free to explore or change times. How did you get around this? Any help appreciated!
NomadicMatt
You can get visas on arrival or, say in the case of Myanmar, any of its embassies in a nearby country. As for onward tickets, Vietnam is the only country I know that asks for it!
ARN
Nice Article! I have a question though, how do you travel within the country? I mean what is your most preferred & economic choice?
Amy
I’m about to plan a 5-6 month trek through South America (I’m living in Colombia right now) and this was super helpful. I’m been pretty overwhelmed with the idea of it but it was good to remind myself to just get the general structure of my trip and trust that the travel gods will be with me through the rest.
Also I hope you enjoy your time in Issan! I lived there for a year and half teaching English and I absolutely loved it!
Nicole
What amount of time do you think is right to spend in each place? Or what is the perfect blend of travel days vs non-travel days for you?
Tammy
Great Read. I’m not a planner at all, kind of just my own thing and go with the flow, but I enjoyed this post
Izzy
I haven’t done South East Asia yet, but it is definitely high on my list of places to go. It’s a long list! This article is a great guide for planing my own travels, thanks!
Carol
I like the “leave it loose” methodology in theory. But when traveling somewhere with large distances (such as I recently did in Argentina), you really need to cover the distances with air travel, which can be more expensive if planned last minute. How do you deal with that? And what one piece of advice would you give me to help me break my iron fisted grip on planning?
NomadicMatt
If you want to fly, you book as close to d-day as you can and just deal with the price! But even planning a certain date gives you flexibility to go with the flow on the inbetween time.
Rachel
One thing I do after deciding which country /countries I’m heading to is to go on google image and type in the country name… I’ll look for any photos that amaze me and track down where the photo was taken. I’ve also done this with travel guide books that have a lot of photos. It’s led me to treehouses in Laos and to a stone church half-buried in lava in Mexico.
Bruce
So Matt what do you do about exiting flight that is required to enter Thailand? Can you get around it when you are planning on entering and exiting the country by train or bus as you visit the surrounding countries?
NomadicMatt
You can get a train or bus if you want but they never ask for proof of onward travel. Don’t know anyone who has ever been asked and I’ve never been.
jay
Great Read. I’m not a planner at all, kind of just my own thing and go with the flow, but I enjoyed this post
Jeff
Hey Matt,
What application did you use to plot your maps? I want to do the same thing for my current trip. It looks like it’s just google maps, but how did you connect the different destinations to each other?
Thanks,
A Fellow Traveler
Rob Rachowiecki
Matt, You say that Vietnam asks for onward tix. Two of us plan 6 months in SEA arriving with a OW ticket LAX – Bangkok and then flying home whenever we are done. Who knows where we’ll end up:) We don’t want to be tied to have to return to Bangkok from Manila or wherever. What do we tell the land border guards when we enter Viet Nam?
Aaren
If you’re spending a year abroad do you still recommend an itinerary? I feel like there basically zero time crunches when you have a full year. Should you still plan cities?
kath
A question about this iprocess in regard to Europe – I was reading that booking train travel in advance is good or even important. Do you need to be less spontaneous in some destinations and get some stuff booked?
Claire Moran
Hi Matt
Thanks a lot for your post! Really helpful 🙂
Do any towns/spots in South East Asia spring to mind as places to spend a few weeks? I’m looking to balance work and travel, it’d be great to find a couple of bases (especially in Vietnam, eg Hoi An) where I can do a bit of both.
Any thoughts at all would be so appreciated!
Thanks again for a great post and site.
Claire
Matthew Andruitti
Lord, a two solid months to travel through Southeast Asia!! I would die happy if I had an opportunity to spend so much time there, because I love that culture so bad!) I always planning my travel routine in the fashion that I starting my route from India, then getting closer to Pacific Ocean. The one very pace I always have stayed for more than two or three dais is always the north of Thailand, because of its outstanding marvelous mountain scapes. How is it goes as usual: I’m arriving at the city by plane from Bangkok, meeting some locals to rent a room for a week and something, renting a motorcycle or basic scooter by Cat Motors company, then sparing all my time by riding through the mountains and taking pics) If you have seen the Motorcycle Diaries movies, you may figure out for sure what it looks like))