Ask Colin: Deciding Where to Travel

I know you’ve traveled a lot, and I truly want to travel, maybe full-time someday, too.

The problem is I can’t decide where to go! Every place looks amazing to me.

I think you’ve had other people choose for you before; any advice on how to do that, or how to decide where to travel, in general?



Hey Heidi-

It’s wonderful that you want to see more of the world!

Travel can open our eyes to a wider range of possibilities, and can help us to three-dimensionalize our perspective of the world.

It’s a stellar investment to make in oneself, whatever age one happens to be.

The specifics of the trip are often less important than the experience of stepping beyond one’s familiar routine, geography, and culture—so there are countless ways to approach it.

If funds are low, visiting the next town over, roadtripping to the nearest large city, or even taking the time to more thoroughly explore your hometown as if you were a tourist can net you some of the same benefits as traveling overseas.

Traveling longer-term is a big commitment, and definitely not for everyone. I tend to prefer it, personally, because it allows me to slowly acclimate to a place, not feeling like I need to rush and not feeling like I can’t put down some roots, develop some relationships, and generally take my time: renting a home base, going to the grocery store, and walking around with no real destination—as opposed to the time-constrained reality of wanting to cram as much as possible into just a few days.

There’s a lot to be gained from any shape or style of travel, though, and there’s certainly value in visiting a wider variety of destinations: including the ability to compare and contrast places, rather than staying a long while in just one or two locales, and thus, lacking the means to make more diverse comparisons.

Having a bit of both experiences—depth and breadth—is optimal, but most of us end up leaning one way or another, much of the time. And that’s okay, too.

In terms of deciding where to go, your style of travel can help you make that decision, as can your budget, what you hope to accomplish while in the area, and other personal ambition-related specifics.

If your budget is relatively constrained, you might consider visiting a place where your money will stretch a bit further, rather than going someplace where you’ll be relatively less capable of doing what you want to do.

It’s tempting to visit famous places like New York City and London and Shanghai and Moscow, for example, but you will almost certainly be able to afford a better place in a more central part of town if you visit Chicago instead of NYC or Edinburgh instead of London.

There are absolutely benefits to visiting larger, better-known, and often more densely populated parts of the world, but your finances will stretch further if you choose something on the medium to medium-high end of the density spectrum. Having more of your budget left after paying for essentials means you’ll be able afford better food, better drinks, more museum passes or theatre tickets; whatever your ambitions, you’ll be more likely to achieve them, without breaking the bank, if you opt for the less-spendy place.

This won’t always be an option, of course, as many of these big, expensive cities are big and expensive because they have things that don’t exist and cannot be easily replicated elsewhere.

All else being equal, though, I almost always prefer to visit medium-sized and smaller cities, because they often provide a better sense of the local culture (cities above a certain population tend to lose a bit of their rough edges, due to globalization and the necessities of scale) and allow me the freedom to adventure more casually while still staying within my budget.

It’s also worth figuring out which sorts of destinations you latently prefer, and then deciding if maybe you should visit the opposite.

I bring this up because I’ve found that, yes, it can be wonderful to visit places you’ve always been curious about, and maybe even dreamed about visiting. But it’s often even more rewarding to visit someplace about which you know less than nothing, providing you with the opportunity to experience the place without expectations or presuppositions—which is a lot trickier to accomplish when you’re visiting a bucket list travel destination that you’ve been dreaming about for years.

If you choose to go this route, there are many ways to choose an unfamiliar place to visit; randomization, crowdsourcing, and shopping for sales are my favorites.

Randomization can take many shapes, but I enjoy coming up with strange superlatives to use as my selection mechanism: my girlfriend and I decided to visit the Northernmost location on the UK train map for Christmas, once, and our time spend in Thurso, Scotland was lovely. I also sometimes look through a list of names of places in a particular region and choose the one that I think sounds the most interesting, based only on the name.

You can also have other people choose your destination for you.

For my first seven years on the road, I had my blog readers vote on which country I would move to every four months, choosing a city within that country to call home, after all the votes were in.

I riffed on this model over the years, in one case deciding I wanted to see more of the US, so I had my readers vote on a state and I chose a city within that state (I ended up in Memphis, Tennessee).

Please feel free to steal this concept and make it your own, even if that means doing a more concise version of it: having your Facebook friends vote, or having your Twitter followers vote on which country you should visit from a list of countries you’ve decided on ahead of time.

Finally, you can let the travel industry choose for you, shopping around for sales and selecting the place that’s cheapest to get to from your starting point.

I often do this when I’m staying in one place for a long period of time, but still want to travel semi-regularly without breaking the bank.

I love a good, short, cheap trip, and you might be surprised how inexpensive travel can be if you allow yourself to explore options that may not be immediately obvious; and that’s especially true if your travel thus far has mostly consisted of pre-packaged trips, or other high-end travel experiences (as is the case for many people).

There’s a wonderful site called Rome2Rio that cobbles overland (car, train, and bus) trips and flights together into multi-piece mega-journeys. You say where you want to go, and it gives you a rough price breakdown of what it would cost to cover different portions of the trip using different modes of transportation. It then makes it easy to purchase tickets, if you so desire.

Google Flights is also a helpful tool for figuring out when to buy plane tickets, showing you the difference between traveling on different days—so you can see how much money you would save if you shifted your departure or return dates, by a little or a lot—and your options in terms of using different airlines or airports.

My usual method for this style of travel is to give myself a budget, what I’m willing to spend for a weekend away, and to then look for creative methods of making that trip happen.

Sometimes this means I’m taking a train or a Greyhound bus, sometimes it means I’m driving the whole way, sometimes it involves a cheap flight or two.

For a variety of reasons I tend to prefer traveling overland whenever feasible: this allows me to see more of the “spaces between places” that I would otherwise miss, but it also tends to be better for the environment and my bank account. Such trips also tend to seem a lot more interesting and less stressful/frantic to me, compared to those based entirely on flying, but your personal preferences may vary from mine in that regard.

Results will vary and preferences will vary, but you may find that you’re able to travel more frequently than you think if you adjust your expectations, decide that you will appreciate wherever you end up for what it is (rather than judging based on what you want it to be), and lean in to the multitude of valuable frictions and novel experiences you’ll likely encounter along the way.

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