Un-Plan Your Trip: Embracing Unstructured Time

Think for a moment about your very favorite travel memories. The spontaneous soccer match with those university students in Beijing. The time a street vendor tipped us off to the sexiest secret tango club in Buenos Aires, and we actually went. The day we got really lost on back roads, but then suddenly found ourselves overlooking the canyon at sunset. You might have noticed that many of your favorite travel memories have something special in common: they were completely unplanned, they were those carefree moments you didn’t expect.

The secret to these memorable moments is two-pronged. The first is to loosen the reigns on your itinerary. The second is to take up a few simple habits and activities to invite sweet serendipity your way.

Here are six simple suggestions to try out during your next travel adventure.

Leave 20% of your time unplanned.

If it’s a 10-day trip, that means you should leave 2 days completely unplanned. If you’re going away for a month, make that a whole week of time sans structure. Don’t take free time in blocks, but rather sprinkle it evenly throughout your trip. There’s certainly nothing wrong with doing your research and having a to-do list of local sites and attractions (actually, not only is there nothing wrong with that, but it’s a really good idea). But remember to keep that, like all things, in balance. So pair that ambitious sightseeing tour with a good dose of rest and easy wandering. As you travel, it’s inevitable that you’ll spot intriguing-looking side streets and overhear murmurings about the weekend ramen festival. Give yourself the luxurious flexibility to jump at those chances as they come.

Cover less ground.

Sure, you could hit 5 cities in 11 days. It may sound impressive, and the pages of your passport will bear a dazzling array of new stamps, plus your Instagram feed will rouse distant envy from all who gaze upon it. But that impressive picture is just that—a picture— and not a reflection of what you really experienced: rushed meals, predawn wakeups to catch the next flight, and missed opportunities to connect with the people and culture. So cross a few cities off your list, and allow yourself to stay, revel, and soak in the places you visit. Good trips are about quality: quality of your mind, quality of your emotions, and the quality of the connections you craft with friends new and old.

Besides, it takes a full day or two at least to get your bearings, figure out how the metro works, get the hang of new customs and calculate a new currency. Giving yourself enough time to really acclimate (even if it means seeing a couple less places) means you’ll travel more relaxed. Being more relaxed means you’ll better enjoy yourself, and as an added bonus, you’ll get more chances for chance encounters—the stuff memories are made of. Do less, feel more.

Chat with locals.

Don’t be shy! Strike up a conversation with your café waiter, the sidewalk jewelry vendor, the lady behind you in the line for the bus. The fascinating thing about conversation is that you never know where it might lead. So go ahead and make the first move! You’ve got nothing to lose (and hey, in the worst case scenario, you’ll probably never see these people again). If there’s a language barrier, be brave, improvise, and just do the best you can with what you know.

Not sure how to get the conversation started? It seems cliché, but the weather is one thing we all have in common, and it’s pretty sure not to offend anyone as an icebreaker. From there, ask people about anything that you’re curious about (while respecting boundaries, of course). What does that traffic sign say? Why do the trash bins have those funny lids? Which restaurant has the best empanadas? Where’s the best place to go dancing? What’s your favorite museum?

Just hang out somewhere.

Go to the kinds of places where people are hanging out, and follow suit! Cafés, public parks, and college campuses will be full of people enjoying some unstructured time to themselves. Let go of “go-go-go” and enjoy a few hours picnicking, people-watching, or playing a casual game of chess. If there’s a portable game or activity you enjoy, like frisbee, watercolor or playing the piccolo, pack it up and bring it along. Doing an activity you enjoy in public can be a wonderful way to relax your mind, soak in a new place, and start spontaneous conversations with locals—which (return to step 3) could lead you anywhere!

Read flyers.

While you’re soaking in the culture and hanging out at a café, school or community center, look around. There’s sure to be a bulletin board or some flyer signposts. Don’t be shy— sidle up and read what’s happening! You may spot a great outdoor concert, evening poetry reading, or a special party that’s not in any guidebook. (And since you’ve already read step 1 and set aside 20% of your time for such spontaneous on-the-fly ideas, you’ll have the available time to jump in and check it out!)

Rent a bike.

Renting a bike with no destination in mind is one of the best ways to see a new place without much structure. You might choose a neighborhood or two that you want to poke around, or just set out and see what you find. You can even remember step 3 and choose your route by asking a local, “Where do you recommend I bike today?” If you’re not comfortable cycling, walking around can be just as rewarding. Wear some comfortable shoes and leave the heavy purse at home. On foot or bike, you can enjoy the pleasure of following your gut, sniffing out cool cafés, secret gardens, and other wonderful local surprises like a serendipity sleuth.

These 6 steps are only a starting point for your renewed relationship with uncertainty and un-structure on the road. Uncertainty, though a bit scary at first, is your friend. Embrace it and discover more magical moments, more unbelievable chance encounters, and more lifelong memories that your imagination could never have dreamed up on its own.

Before departing, it’s also important to practice the local language. Sign up for some language lessons before your next trip.

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