12 Ways to Be More Spontaneous When You Travel

Considering how precious vacation days are and how expensive travel can be, the urge to plan things out so you get the most from your travel time and dollar is almost irresistible. And it’s never been easier, considering the thousands of websites, apps and guidebooks full of travel information on just about every possible destination.

But something is lost when you can anticipate — nay, almost script — nearly every component of the travel experience. Not so long ago, the vagaries of travel were considered a normal and even welcome part of the experience; with daily life being so predictable, a good antidote was a wildly unpredictable trip to a faraway place.

To recover some of that wildness, many travelers are pulling back from “overplanning” and trying to craft a slightly more spontaneous trip — easier said than done for folks who are planners by nature. If you’re not sure where to start, I’d suggest thinking of spontaneous travel not so much as letting things happen to you, but more like “planning on the fly.” Have a general idea of what you want to do and see, plan out those things that you feel you just can’t leave to chance, and then improvise from there.

Below are 12 tips for having a more spontaneous trip.

If 80 percent of life is just showing up, then the most important things you need to plan are how to get where you want to be and a place to stay once you get there. If you choose a central location that has ready access to attractions and public transit, you are 80 percent of the way to a successful trip, even if you plan almost nothing else. With at least a few of the things you know you want to do nearby, once you tick those off you can wing it almost completely without feeling like you missed something important.

As I talked to folks about their most memorable spontaneous travel stories, a fair number involved scrapping a careful plan almost entirely, usually in favor of something impromptu. Of course, you’re less likely to change your plans if you’ve already dropped a couple hundred nonrefundable bucks on a hotel room. If possible, don’t keep yourself tethered to one spot for your whole trip. Unless it is peak season, most hotels can extend your reservation while you are still there — so book a shorter stay, and then if you decide not to move on, extend it. Booking a nonrefundable hotel for your first and last nights is less risky, since your flights are unlikely to change, but leave yourself a little more flexibility in between.

Turning your travels into a forced march from one attraction to the next can be grueling. It’s a vacation, not a whistlestop political campaign. If there are some things you absolutely must see, assign a time to get that done (early in the morning often works best), and let serendipity rule the rest of the day.

It’s hard to resist assigning at least one activity to every day, and then to start ticking them off once you arrive. We visited Berlin last week, and I admit that my thinking went a little bit like this: “Berlin … the Wall, Brandenburg Gate, the Reichstag, the East Side Gallery, LEGOLAND for a kids’ outing, Potsdamer Platz … one or two per day, done.” As it went, we didn’t have the sightseeing stamina to go into the Reichstag, and instead ended up playing a game of tag on the giant lawn out front — which continued through the Tiergarten, past a very cool rock art exhibit.

Which part of the visit sticks with us the most now that a few days have passed? The Berlin Wall has few equals as a historical attraction with staying power — but the game of tag in the Tiergarten is up there.

Leave at least one entire day open, even if you have to crowd another day with a couple of activities. This way you can either fill the day or be content to wander around and find your own rock art adventure.

No matter how much planning you do, it is almost inevitable that the facts on the ground once you arrive will be different from what you expected. Distances are shorter or farther than you thought, you see stuff on the cab ride into town that seems interesting, or you overhear chatter about local attractions that aren’t in your guidebook. Leave yourself the option of figuring things out once you see how things really are.

For those things for which you do feel the need to have a solid plan, use all the tricks at your disposal to make them happen smoothly and as intended. Knowing the operating hours, taking the best route to and from, and having advance tickets to avoid lines will help you free up more time for spontaneous activities.

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Thanks to capacious and information-packed review sites, travelers can make far better choices about almost every part of the travel experience. But if the review sites lead to fewer unpleasant surprises, they also present the risk of fewer pleasant surprises, which are of course an important part of exploring the world as a traveler.

The days of walking into a restaurant with no idea of what might show up at your table are mostly history, but you can reintroduce the element of surprise by not making every meal choice based on a Yelp review. This isn’t the best approach for everything — review sites can help you avoid hokey attractions or awful meals — but if the menu looks appealing and the place is bustling, why not skip the star rating and try your luck?

A smartphone can be the ultimate way to plan on the fly. The simplest and often most useful function on your phone is the “near me” or “explore nearby” options on your mapping app; you can type almost anything into the search field — museum, restaurant, grocery store, coffee — and receive a decent suggestion.

Location-based apps like Foursquare can also offer superb results, with the added benefit of frequent use by locals. I checked results on Foursquare in a few cities that I know very well, and the suggestions were pretty good — all places I would recommend to a friend who was visiting the area, plus some others I didn’t know about and will have to check out myself.

While many daily newspapers are in trouble, locally owned (usually weekly) community newspapers are thriving. They’re packed with listings for activities, festivals, concerts, classes and more. Many big cities have alternative/entertainment weeklies, while smaller communities may have more news-based publications — but all of them are geared toward getting information out to the locals, and to travelers who are clever enough to have a look.

Few tactics rival learning about nearby attractions from a bona fide local. You can find them everywhere — the hotel front desk, restaurants, bars, grocery stores — anywhere you come into contact with folks who are working, shopping for mundane items and going about daily life.

Staying at a B&B may offer the ultimate in “ask a local” opportunities; the folks running the house usually live on the premises and understand that helping their lodgers get the most from their stay is part of the reason to choose a B&B over a hotel. To be sure, I have run into a few curmudgeonly B&B hosts over the years, but these places tend not to get the best reviews. You’ll definitely want to use the review sites when picking a B&B, paying particular attention to how helpful and available the proprietor tends to be.

Getting off the tourist circuit can offer up plenty of opportunities for unexpected encounters and experiences. Going to a swimming pool or library or taking a yoga class, for example, can put you into contact with people who might get you off the rutted tourist roads and into the places and even homes of the locals, and then you never know what might happen.

Pursuing your own passions can often be the best way to open yourself up to these kinds of experiences. For example, when wearing a rowing shirt while traveling in Hawaii, I was approached by a local who owned a two-person ocean rowing scull who could rarely find another rower to go out with him. He asked me to join him, and we rowed out into the ocean and around a small island, where swells wrapped around the back of the island to meet in an explosion in the middle. We caught one of the waves, blitzed along at full speed and maneuvered at the last second to avoid the exploding waves as they met. Talk about an unplanned adventure.

Have any tips to help inveterate planners loosen up a little? Add them in the comments!

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