March 7, 2017

How to Choose Where to Go on Your Next Trip

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“I may not have gone where I intended to go, but I think I have ended up where I intended to be."
—Douglas Adams

Where are you going on your next trip?

If you’re like us, the number of destinations on your travel wish list probably exceeds your vacation days. Of all the contenders on your travel wish list, which is the one you should set your heart on, and dream and plan for? This question might be further complicated by indecision over when you’ll go and what you will do. Most folks have professional and personal lives that place limitations on the amount of time available for leisure travel, not to mention financial constraints. Moreover, the travel you want to do (Paris in the springtime!) may compete with the travel you must do (that regrettable wedding in Topeka!).

Trying to generate a destination without any forethought or deliberation can be a non-starter. If you don’t travel frequently, you might be feeling even more pressure to choose and execute your trip perfectly; anxiety over planning can be a major stumbling block to actually getting out there. When you add up all the variables, it’s easy to get overwhelmed by all the possibilities, all the options.

While we can’t dictate your next destination (SEATTLE—oops, sorry), we’ve thought of some questions you can ask yourself to help you pinpoint what you’re really hoping to get out of your trip. From there, you can winnow the mental list of places you’d like to visit to just one: your next travel destination.

Do a travel brain dump

You may already know that your next trip will be either to Spain or Austria; if that’s the case, you may not need to generate a travel list to help you pick a contender. But if you are finding yourself inundated with options, it can be helpful to put everything on paper in order to tame the chaos.

To get a good list, the first step is to do a brain dump. You might be familiar with this rather inelegantly-named activity if you’ve read David Allen’s Getting Things Done. Allen argues that in order to accomplish things, the first step is to list everything that must be done—it’s only after seeing the totality of your thoughts and ideas when vague to-dos can begin to be translated into actionable steps.

To do a travel brain dump, consider the following: Where would I like to go? When do I want/have to go? What do I want to do? Then just list everything and anything that you can think of. This list can and should be quite long, and the sky’s the limit. Don’t worry about categorizing or thinking through logistics at this point.

The travel brain dump is great for seeing all of the places you might want to go and things you might want to do. It’s a list you can return to again and again, adding and removing items as your interests and commitments evolve. Once you have this big list, you can start thinking about what seems most doable, fun, and affordable for you right now.

Determine your top travel priority

Check out your master list. Right away, you’ll probably recognize some destinations or activities that, on second thought, aren’t actually that appealing or are simply not possible right now. You can save those for another time, but for now, think about your top travel priority—the number-one consideration in your deliberations. Is the most important thing a specific location, or is it a time of year or activity? Once you know what’s most important to you, you can refine your list by asking more pointed questions, the answers to which will be more specific and context-based.

Let’s pretend that next year, you can take a 10-day trip in September or October—this part of the equation is non-negotiable. From this central priority you might ask: how far afield can you realistically go in that amount of time—that is, would it be better to go somewhere that you can get to more quickly, or are you willing to power through the travel time and jet lag in order to get to a particular destination? Is somewhere better in terms of seasonal activities, sights, or cultural events? Note that there is no right answer to these questions. One person might be able to go to the other side of the world, whereas another won’t want to travel more than four or five hours. Just be honest about what you want and are able to do.

Say you’re flexible about where you go, but you want to do certain things either there or en route. For example: museums, theatre, and nightlife? Quiet walks through an idyllic countryside? Snowmobiling to an ice hut? Running across a black sand beach? Seeing a bunch of castles, or churches, or monuments? Beginning your search with your most-desired activities can lead you to discover some potential destinations you may not have considered: ecotourism in Bolivia, winery-hopping in Hungary, cooking classes in Morocco. Or perhaps a week of hiking, swimming, and visiting out-of-the way restaurants in an area closer to home that you didn’t even know existed.

These questions will lead you into a phase of research: local weather, average prices for accommodations and food, the exchange rate, stuff to do, and so on. While we can’t guarantee it, it’s likely that as you gather this information, someplace will latch on to your conscious or subconscious mind. You’ll find yourself daydreaming about the sights and sounds of a given place, mentally running through your travel wardrobe, wondering how to say phrases in a different language. It’s a very good sign that place is where you want to go next.

Note: don’t throw away the information you’ve amassed on other locations, though—having this knowledge ready to hand can help you plan a trip further down the road, or be ready to act if an unexpected opportunity drops into your lap.

The journey: or, how to get to where you’re going

Now that you know where you’re going, how will you get there? Sometimes, for the sake of simplicity, economy, or logistical necessity, you may find yourself booking a flight or reaching for your car keys. But be sure in the course of your research to investigate if there are transportation options that you may have not considered that could add enjoyment, convenience, or a different facet to your trip.

You could drive your own car down Route 66, but renting a convertible or driving a motorcycle might be more fun. Maybe instead of taking a train between Paris and Rome, there’s a discount flight that will have you smooching your honey on the Spanish Steps that much more quickly. If you plan to take a driving trip, renting a camper van or Airstream could let you take your lodging with you. Instead of driving to one of America’s national parks, you could take the train.

Also consider transportation at your destination: once you’re there, will you stay put or move about? For example, will you rent a car to drive over the Alps, take a plane or train, or traverse on foot, hut-hopping as you go?

Letting go of worry so you can go

Finally, you know where you want to go. You know the time of year, what you’ll do when you’re there, and how you’ll get there. Yet, something’s keeping you from buying that plane ticket or putting down the deposit on the dog sled expedition. What on earth is happening? You were supposed to be excited—after all, you wanted this.

There are many things you could worry about as the trip moves from the realm of fantasy to actuality. Especially if you aren’t able to travel often, the pressure to plan a flawless trip can have you second-guessing all of your decisions. As hard as it might be, try to put that worry on the shelf. Sure, it’s true that a cheaper ticket might become available, or that there’s an awesome activity or event you won’t know about in time. While it’s easy to get consumed by analysis paralysis, in the end your journey can’t start until you commit to packing your bag.

Take that leap of faith that you have chosen exactly where you must go and why you must go, and that the right time is right now.


John Warren - November 19, 2019

Check out the book—and/or website—"Atlas Obscura." An atlas of fascinating, unusual, and mysterious places. Such as the The mysterious Doxey Pool, on the path running across the top of the Roaches, a gritstone escarpment not far from the Staffordshire/Derbyshire border, home of a “malicious mermaid.” Now, I’m sure there is no such thing as a malicious mermaid, although I’m willing to believe in mermaids.

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