How to Decide Where to Go on a Long-Term Trip

Plan Your Round the World Trip in 30 Days

So you’re taking the plunge!  You have decided to stop making excuses and make your dreams become reality.  You are forgetting the naysayers and heading off on a long-term trip.

Now what?  The world is huge, and you want to see as much of it as you can.  Or do you?  So many things come into play when planning an extended trip, especially if you’ve never done it before.

First Realization:  You can’t go everywhere


When my wife and I made the decision to take off on our adventure, we were lost on where to begin.  Our initial plan was to travel for an entire year.  A year! “We’ll be able to go everywhere and see everything,” we thought.


One of the biggest mistakes people make when planning a big trip is planning to do too much.


This is the very first thing one must realize when planning to travel long term, whether it’s a career break, a RTW trip, a family adventure, or a retirement trip.  You simply won’t be able to go everywhere and see everything.  It’s not possible.  Unless you’re filthy rich and can afford to fly everywhere all the time, you are going to have to prioritize and save some destinations for that next trip (and the one after that).  One of the biggest mistakes people make when planning is planning to do too much.

Extended travel is different than a one or two week vacation.  It’s very difficult to sustain the pace that most travel at when going on vacation.  Downtime is a necessity, and you’ll probably travel at a much slower pace than you’re used to.  Seeing site after site and traveling to new cities every few days will get old after a couple months.  You will get burned out at some point, no matter how quickly or slowly you travel.  Trust me.  And if you travel at a frenetic pace, that burnout will come much quicker.

Obviously how much you do or don’t plan depends on a wide variety of factors, one of which is who you are traveling with. If you’re going solo, you only have yourself to worry about, so in a way, it’s a bit easier because you are the only ones making decisions, and you know your own personal level of comfort.

If you’re traveling as a couple or with a friend, it gets trickier. Make sure you and your traveling partner discuss how quickly you want to be going. And be sure to build in time to slow down and at least give yourself the opportunity to chill out for a bit, even if you think now that you won’t need to.

If you’re a family, this is more important. Slow travel fits families perfectly, as kids (especially the littler ones) tend to get exhausted when trekking from hostel to bus to new city to new hostel to bus over and over again. You need to give yourselves a chance to breathe, so keep this all in mind when coming up with your itinerary.

>>Plan your route and start pricing multi-stop, RTW plane tickets.

How to prioritize

The best thing to do when first planning that long-term trip is to start researching as much as you can and question what your top priorities are.

  • Are there any cities/sites/experiences you have always dreamed of visiting or doing?
  • Are you a city person, or do you love the outdoors and hiking and camping?
  • Would you be happy circling the globe checking out the world’s best beaches?
  • Are more you more of a museum and culture person?
  • Is food extremely important to you when traveling?
  • Do you want to volunteer, work, or take any classes while abroad?
  • Do you enjoy a combination of everything above?

Other questions to ask yourself revolve around the style of travel you enjoy and what method of travel you have in mind for your trip.

  • What types of accommodations do you plan on staying in?
  • How do you plan on getting around?
  • How much advance planning do you want to do, and how much of your trip do you want to leave open to spontaneity?
  • Will you want to take any guided tours on your trip?
  • Will any of your must-see destinations and activities require tours?
  • Have you educated yourself on multi-stop, RTW plane tickets vs. buying one-ways as you go?
  • Do you have a budget number in mind?

The answers to all these questions will help shape the route of your trip.  Your head may be spinning, and you may feel a bit overwhelmed, but don’t worry, it’s natural to feel this way at this point of the planning process.  Remember you’re at the very beginning of this whole thing.

It’s important to be honest with yourself when answering these questions.  Don’t feel like you have to take part in an activity you wouldn’t otherwise care about.  If you don’t like camping and hiking, that’s perfectly acceptable.  If you couldn’t care less about museums, that’s okay. This is your dream trip, not someone else’s – remember that.

If you’re taking the trip with other people, whether it’s a partner, spouse, friend, or family, come up with a plan for choosing where to go. If you’re going with your kids, make sure they have a say in things as well – this will get them excited and feeling part of the decision-making process (what kid doesn’t want to offer their input?). An idea might be to give each family member the opportunity to choose one must-see place or activity that no one else can veto or complain about.

 Fill out this form if you want personal help planning your trip from a BootsnAll team member.

Research tools to help

If you’ve never planned a trip longer than a few weeks, finding the tools to help in your decision making process can be overwhelming.  The resources out there are many, and we used a combination of all of them when trying to find the answers to all these questions.

We began by reading as many travel blogs as we came across.  There are literally hundreds of thousands of travel blogs out there, many revolving around RTW, long-term travel and with a wealth of information.  There are so many now that you should be able to find one that fits your niche perfectly – whether you’re a solo traveler, a couple, a family, a career breaker, gay, straight, whatever – you’ll find someone to connect with. We also took a trip to our local library and checked out travel guidebooks.  They are usually old and out of date, but at this point, we just wanted to read about different destinations and what they had to offer.

Travel forums are also an invaluable resource when planning a trip.  BootsnAll’s forums are broken down and organized very well, with different message boards for each region of the world.  We even have a forum dedicated to RTW and Vagabonding travel.  And if there’s one thing that travel lovers enjoy doing, it’s talking about their experiences.  I was floored by the amount of people who were willing to help and share their input when we were planning our trip.

Check out the following resources for more information on planning:


While the budget is a very important piece of the puzzle, it’s not essential to have an exact number, yet.  One thing you do want to do, especially if you don’t have a lot of travel experience, is try to figure out what it actually costs to travel in the different countries around the world that you are thinking about visiting.

At this point, we just want to estimate (we’ll dig into actual costs soon, don’t worry).  And keep in mind that any budget number you see is based on someone else’s experience.  There are some who can travel Thailand on $10 per day, and some who can’t do it for under $75 per day – EVERYONE IS DIFFERENT!

Here are a few tools to help you estimate costs:

The Pillars

Patagonia was a must-see for us

After much research, we started getting an idea of what it was we cared about most. Putting priorities on where you want to go, what you want to see, and the activities you care most about create a framework for the trip.

Hiking the Inca Trail to Machu Picchu, seeing Iguazu Falls, hiking around Patagonia, spending some time lounging on islands in SE Asia, visiting Angkor Wat, and catching a glimpse of the Taj Mahal ultimately topped our lists.  While there were certainly other places we were dying to go, these six places and experiences were most important to us.  They became what we called our pillars, our must see’s and do’s, and ultimately the framework for our RTW trip.

Pillars don’t always have to be a city or place either – they can be an experience. Volunteering can be a pillar. WWOOFing can be a pillar. Surfing, hiking, biking – whatever interests you most about the world – plan your trip around those. This is the time to dream. Pillars ultimately come down to all those places and things you’ve always talked about seeing and doing.

It was not easy to narrow this list down.  Certain experiences just had to be cut, no matter how badly we wanted to do them. But it all goes back to that number one realization.  You can’t do and see everything.  Some activities and places, while important to us, had to be sacrificed, mainly because of cost.  While going to the Galapagos was something we both wanted to do, spending $7000-10,000 on a 10 day trip there was simply not feasible (wish this article was published before we left).  Traveling for a longer period and experiencing more was more important to us than seeing the Galapagos.  The same went for visiting regions like Europe and going on safari in Africa.  We wanted to, but they were ultimately too expensive for this trip.

Planning around your Pillars

Once we felt good about our pillars, the planning process became much easier.  Because all of our pillars (except the Taj) were in either South America or Southeast Asia, those two regions were where we would spend most of our time.  Both were renowned for being cheap backpacker destinations where overland travel (our preferred method for the trip) was both inexpensive and easy, so they fit in within our travel and budget plans.

Considering guided tours

Keep in mind that some of your pillars may require a guided tour. For example, if you want to hike the Classic Inca Trail to Machu Picchu, you can’t do it independently – it has to be with a tour group. Or maybe you simply want to take a few tours here and there so you don’t have to plan every single part of your trip.

If you want or need to take a few tours over the course of your trip, start looking into them now, particularly for ones that book up well in advance (like the aforementioned Inca Trail hike – it can book up 6+ months in advance, particularly during high season).

We recommend Intrepid Travel for any guided tour you might take. They embody the spirit of indie travel by using small groups and locals to guide their tours. Check out some of their offerings during this stage of the game to have an idea of what’s on offer and how far in advance you need to book.

Read Maybe Organized Tours Aren’t So Bad After All? and Can Families Travel Indie Style on a Tour?

How to plan the route

Everyone is different in how they travel.  Some plan everything out.  Some plan nothing and leave everything up in the air.  Most want to be somewhere in the middle, though, and we were no different.  We knew that some activities and places were going to involve some advance planning, but we wanted to leave enough time open for spontaneous activities.

Many things must be taken into consideration when planning where to go first and getting a rough framework in place.  Taking thing like weather, high season vs. low season, festivals, and holidays into account are all part of the planning process.

If spending a lot of time on the beach is what you’re looking forward to most, you want to make sure you’re not there during monsoon season.  If Carnival in Rio tops your list of activities, you’re going to want to plan far in advance as accommodations book up quickly.  If hiking the Inca Trail is most important to you, you have to know that it is closed the entire month of February and you may have to book up to 6 months in advance.

Read about How to Use a Stopover to Maximize Your Flights

Second realization:  Don’t try to create the perfect itinerary

We took our chances with the weather in SE Asia

While missing monsoon season, always traveling during shoulder season, and being everywhere at the perfect time sounds amazing, it’s practically impossible to create that perfect itinerary.  You’ll drive yourself crazy trying to get everywhere at the perfect time.  So just stop now and realize that you will have to make some decisions and sacrifices when planning out your route.

Remember that everything has its pros and cons.  Travel during high season typically means best weather but also brings larger crowds and higher prices along with it.  Low season has lower prices and less crowds, but it could rain, snow, be bitterly cold or unbearably hot.  Shoulder season has a great combination of lower prices, less crowds, and the possibility of either good or poor weather.  You’re always taking a chance when traveling during shoulder season.  It all comes down to personal preference in the end.

Check out the following articles and video about planning the itinerary:

How we decided

Because of our budget and length of time we hoped to travel, we wanted to avoid high season as much as possible.  We were also flexible on our departure date, so that helped tremendously. Our plan to spend most of our time in South America and Southeast Asia (while hopefully adding India and another possible destination) created a dilemma though.  The ideal times to travel in both regions overlapped, so we had a decision to make.  Deal with the possibility of wet weather in South America or the monsoon season in SE Asia?

Again, doing the proper research helped in the decision making process.  Talking to people who had traveled in both areas was vital in assisting us.  We ultimately found out that even though May-September is considered monsoon season in much of Southeast Asia, it typically didn’t rain all day every day for months at a time.  While heavy, uninterrupted rain was certainly possible, the norm was for it to rain hard for a few hours each day while otherwise being pleasant.  It also meant that prices and crowds were down during this time, another plus for us.

Since we weren’t the most well traveled people out there (we had only been abroad to Europe for a few weeks at this point in our travel careers), starting in SE Asia seemed daunting to us.  We feared the culture shock and language barrier would be too intense for us (in hindsight, it wouldn’t have been).  Combining all that with the fact that we found a super cheap, one-way flight to Peru in October, and our decision was made.  We would begin our trip in South America.

>> Check out lessons to learn from Adam’s RTW trip

Multi-stop plane tickets vs. buy as you go

Another important aspect of travel to consider is whether or not you plan on buying a multi-stop, RTW plane ticket.  There are many different types of multi-stop tickets to choose from, so make sure you educate yourself about them.

>>Download our free Around the World Airfare Report to learn more about your options

BootsnAll offers Indie, a multi-country flight finder where you can get immediate pricing on your trip and book online if you find a trip you like.  It’s fun to play around with, and by plugging in destinations and dates, you can start to get an idea of what your trip will cost from a flight standpoint. Another option for multi-stop flights is AirTreks, who have been around for over 25 years and have experts to help you craft the perfect itinerary for you.

While choosing this option can take away some spontaneity, it’s all about how you use it.  You can book your entire trip up front with Indie (which would make it more difficult/expensive to change plans on the fly), or you can book it in legs.  If you just want to buy your first ticket and go like we did, you can do that, too.

>>Read Why Planning a Multi-Stop Trip Shouldn’t Be Difficult
>> Read our reviews after shopping for multi-stop, RTW plane tickets
>> Find out how to save time and money on your route

How much should you plan in advance?

Now that our first destination was decided, it was time to take it a few steps further.  How much you want to plan in advance all depends on who you’re traveling with, your travel style, and flight choices.  If you decide to go with a RTW plane ticket, you’re going to have to plan more in advance.  If you choose the buy as you go option, you can simply buy that first plane ticket and decide on the fly if that’s your style.

We bought that first plane ticket to Lima, Peru for departure in mid-October.  But I’m a planner, and I wanted to have a rough framework in place that also allowed for spontaneous decisions.  Hiking the classic Inca Trail was at the top of our priority list, and we knew that booking  in advance was necessary, so we had to plan.  After the Inca Trail was booked, we turned our thoughts towards Christmas and New Year’s.

By the time the holidays came around, we would have been on the road for over two months, and we thought we may want a bit of a break.  We considered hunkering down somewhere and maybe renting an apartment, so we decided to rent one in Buenos Aires for a month around the holidays. Renting your own place for a couple weeks or month is something I highly advise all travelers to do – especially families. It’s great to be able to unpack your bags and have a place to call home for a while.

Our flight into Lima, the Inca Trail hike, and an apartment in Buenos Aires were the only things we booked before leaving.  It left us with a rough itinerary for the first few months.  We knew that we had a few weeks after our arrival in Peru to make it down to Cusco for our hike, and then we had about month and a half to make our way over to Buenos Aires.  That left us with plenty of time for spontaneous travel.  The gaps in our itinerary created the advantage of being able to decide on many destinations while on the road and still giving a rough framework to work with.

Note:  Many people automatically think that booking a multi-stop, round the world plane ticket takes the spontaneity out of the trip, but if you book your flights weeks or months apart, there’s still plenty of time to make decisions on the fly and be spontaneous.

Do what you want to do

The most important decision you can make in all this is to trust your instincts.  There is no right or wrong way to plan a long-term trip.  Some may tell you have to do this or you have to go there, but put trust in yourself.  While others may be more well traveled than you, you know yourself best.  Do what’s best for you.

The best thing you can do is devour as much information as you can and then make an informed decision.  While we can give you the tools to make that informed decision, remember you’re taking this trip because you want something different out of your life.  You want something special that you will remember for the rest of your life, so make your decisions based on what it is that you want out of your trip.

Read more on long-term, round the world travel:

What are your trip planning suggestions for a long-term trip?  If you’ve taken an extended trip or are planning one now, what is most important for you when planning your route?  Comment below!


Photos by chrismar, The Hamster Factor, Evil Yoda, Dimi15, others by the author and may not be used without permission

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Older comments on How to Decide Where to Go on a Long-Term Trip

14 April 2011

Great post on a great topic Adam!

The BEST advice that we got from close friends who had taken a year off to do RTW trips is that a year is just not long enough. It sounds so long when planning, but goes by soooo fast. Even 5 years of non-stop world travel has gone by so fast. Slow travel and deep immersion adds so much to a RTW trip. If one doesn’t schedule in do nothing time and rest, you will burn out and get travel fatigue.

We haven’t had any travel fatigue because we do 6 or 7 months of travel and then do deep immersion in special places for about 5 months. That gives us certain “homes” around the world and allows us as monolinguals to raise our daughter as a fluent as a native trilingual/triliterate in Mandarin/Spanish/English.

We do this in the winter and gives us time to refresh and even do multigenerational travel sometimes with family visiting us to share the experience like my 83 year old Mom touring with us in Asia for 6 weeks this past winter or his Dad and sis who joined us in Spain.

Happy planning all! The prep and planning can be hard, but it is all sooo worth it!

14 April 2011

Also, I DO think that following the weather REALLY helps. It makes a HUGE difference in seeing a place in divine weather compared to day after day of cold/rain/ugly.

14 April 2011

We used a RTW ticket this year, but for next years RTW trip, we will NOT be using a RTW ticket.

There are advantages and disadvantages, LOOK closely.

Megan Hennessey
14 April 2011

Thank you SO much for posting this! After your last RTW post, I was itching to start planning, and used one of the websites you gave to draw up a basic sketch. Yet, there is something so daunting about traveling for an entire year (says the girl who loves holing up in her dorm room). These tips are essential to making sure my RTW trip is the best it can be!

18 April 2011

Love it! I also second Iguazu and El Chalten. Amazing stuff.