How To Decide Where to Travel & Build an Epic Itinerary

So you’ve been dreaming of getting away for a short escape or a year of traveling the world. But first you have to decide where to travel to first!

Anyone who has reorganized their life for travel knows how hard-won and precious that travel time really is – so the pressure mounts to make the most of it.

Even after whittling down the destination options based on logistics like cost, ease of access, language or weather, you’ve still got some seriously sizable territory to choose from.

So how do you choose where to travel to first? Here are some tips on how to decide, and how to build an epic itinerary.

1) Use travel books & movies as inspiration

Do you have a handful of favorite books or films that you’ve always loved for their ability to completely transport you? Turn those journeys of imagination into a real trip!

I was so enamored with the images of England, Italy and India that my favorite author evokes, that I planned a year of travel through those very places: a traveler’s homage to the arts.

When I finally visited the landscapes that I’d envisioned a million times with my nose in a book, my imagination kicked into high gear.

Every stunning view or hidden corner reminded me of the stories I’m still swept away by, making countless ordinary moments deeply meaningful.

2) Travel to your family’s birthplace

Lately we’ve seen an epic trend in travel: following your birthright. When deciding where to travel, think about where your family has come from.

This one seems particularly popular for Americans.

Seeking out a part of your own heritage can forge a surprising connection.

I planned to meet my mother in Italy and take a day-trip to the tiny village where her grandparents lived before emigrating to the United States.

Conducting the research for this trip made planning the trip a blast. We talked to relatives at home, pored over old photos and even did some digging on ancestry.com.

When we got there, we loved to chat with locals who weren’t used to seeing tourists like us. They were as excited as we were about our arrival and the brief exchanges we shared were surprisingly emotional and appreciative on both sides.

With that said, I wish I’d given this trip more time!

When our day was through, I left feeling like I could have learned so much more about the history of that place and my family that were deeply entwined.

If you feel a strong connection to your family heritage or don’t have a clue but want to start to find out, a trip to ancestral lands can leave a unique and lasting impression.

3) Follow your passions

When you go abroad, the location doesn’t have to be the primary impetus. If you have an issue you feel passionate about or a cause you believe in, chase it down and get involved no matter where it leads you!

In this case, it’s more about finding the best fit between you and the work location, exchange organization or volunteer host – making the location almost incidental.

But remember: the unstructured experience of exploring a city, town or entire country usually means you’ll find something you love; the particular vibe of an organization or volunteer situation can make or break a trip.

It’s wonderful to be purpose-driven, just be sure that you research and find the right fit so that dedicating yourself to your work also leaves you upbeat and able to enjoy your surroundings.

4) Leave room for spontaneity

In my experience, the best thing to do when it comes to building an epic itinerary is striking a balance of planning and spontaneity.

Sometimes it’s just about tapping into the motivating force behind your trip that lets it fall into place. What kind of itinerary inspiration will strike you?

Here are a few of the route-planning rationales I’ve attempted, altered and enjoyed – and a debrief of how they worked out in the long run.

5) Roll the Dice

Yes, I have become so utterly overwhelmed by options and so incapable of making a decision, that I have turned to pure chance to make my travel plans.

At the end of my first year of backpacking, there were still dozens of destinations I wanted to explore, and only a month to spend exploring.

What should I do? Where should I go? I wavered every day for weeks before I had to make firm travel arrangements.

Finally, I grabbed two dice out of an old board game where I was staying, wrote down a list of numbered options, and let ‘em fly.

I won’t tell you exactly where I ended up, but I’ll say, I never regretted that decision for a minute. Thanks, dice.

When you’re getting ready to make some decisions on where to travel, give yourself a little time to contemplate what this trip is really all about for you. Nothing is too silly (or too simple) to make for a meaningful mapping of your way through the world.

How did you decide where to travel to? Give us your best stories & trips in the comments!