Author: Adam Seper

Deciding Where to Go

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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.

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 whole year!

“We’ll be able to go everywhere and see everything,” we naively thought, as our longest trip to date was 3 weeks.


This is the very first thing one must realize when planning to travel long term, whether it’s a sabbatical, a gap year, a round the world (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 have an unlimited budget 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 quickly. 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 one 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 fast you think you want to move. 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, open up a doc or spreadsheet on your computer (or go old school with a pen and paper), and start making lists.

Ask yourself 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 (and how much do you actually know about various accommodation options)?
  • 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?
  • Do any of the tours you want to take book up months in advance (you’d be surprised)?
  • Have you educated yourself on multi-stop plane tickets vs. airline alliance RTW (round the world) 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 your route. 

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.

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.


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 $100 per day – EVERYONE IS DIFFERENT!

Here are a few tools to help you estimate costs:

The Pillars

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 – what we like to refer to as The Pillars.

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 our pillars, our must see’s and do’s, and ultimately the framework, or skeleton, 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 thousands 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 within our travel and budget plans.

Suddenly, the puzzle was coming together

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).

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, as all will impact costs and the vibe of the destination you are visiting.

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 and airfare rises around that time. 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

Don’t try to create the perfect itinerary

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 what you deem to be 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:

A real example

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 Southeast 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 departing 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

Airfare options

An important aspect of long-term travel to consider is airfare as it’s most likely going to be your biggest expense. Contrary to popular belief, there are many different options out there, so make sure you educate yourself about them.

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


Indie is more of a do-it-yourself kind of tool, where you can build your itinerary online and get an immediate, bookable price on your flights.  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 (even if you don’t book on Indie, it’s great for planning and estimating your costs, as many people have no idea what flights for big trips like this cost).

AirTreks has been around for over 25 years and has experts who have all been at this for a long time. You can also build your itinerary on the AirTreks Trip Planner and get an estimate of costs, then you will be assigned a personal travel consultant who will talk to you about your goals for the trip, your budget, and craft the itinerary that fits your needs.

Other specialists

There are also other companies all over the world who specialize in multi-stop airfare. Check out the following reviews of 9 companies and airline alliances shopped in research for the Around the World Airfare Report.

Airline alliances

Each airline alliance also offer RTW (round the world) tickets that have strict rules and regulations to follow. But if you have been collecting miles with a particular airline, now could be your chance to cash in. Or if your specific itinerary fits into their rules and regulations, you may be able to find a good deal.

Do it yourself

DIY is the final option available, which means figuring it all out on your own. This could mean buying a series of one-way flights as you go, deciding on the fly where and when you want to go. This often sounds like the best option for those of you who crave spontaneity, but keep in mind that last-minute flights are typically the most expensive, and consider the time you’ll spend in front of a computer searching, shopping, and booking flights while you’re supposed to be traveling.

>>Read Why Planning a Multi-Stop Trip Shouldn’t Be Difficult

>> Find out how to save time and money on your route

How much to plan in advance

Once 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 multi-stop or 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 and you’re comfortable with the possible budget ramifications of doing so.

We bought that first plane ticket to Lima, Peru for departure in mid-October. I hoped to have that perfect mix of having a rough framework in place that also allowed for spontaneous decisions.  Hiking the classic Inca Trail was one of our pillars, 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.

Remember to do what you want to do

If it’s one thing you take out of this nearly four-thousand word article, it’s this: 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:


Photo by Hurst Photo

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