Another strategy: For every five days of your trip, set aside one for planned spontaneity. In the city? Bury your phone in your backpack and explore a neighborhood blind or with a paper map, asking for advice along the way. In the country? Take a drive down a local road and stop whenever you see something interesting: a high school baseball game, a yak farm, a bait shop. (Don’t fish? Then ask for directions.)
Be on a mission
To give some structure to your adventuring, come up with a nonserious goal that will add an element of fun and nudge you off the tourist trail. Make it your mission to find the best bookstore in town, try every brand of local candy or search for the weirdest ice cream flavors. In England, declare that by the end of your trip everyone in the group must choose a Premiere League soccer team to root for when you get home. Locals will surely lobby for their club. In northeast Portugal I vowed to learn a few words of the local language, Mirandese. People were delighted to teach me — though, I imagine, not nearly so much as the English would be to talk about why their football team is superior.
Sometimes an opportunity for a detour or a change of plans will arise that you (or your travel companions) might think is silly or a little nerve-racking.
Should we turn down that side street just to see what’s there? Should we get off at a random subway stop and explore? Stop off at a supermarket to see what kinds of cereal they have? Attend that local community potluck we saw a flier for? The answers are yes, yes, yes and yes. What do you have to lose if it goes well? The second museum or third monument of the day? And what if it doesn’t? You’ll be set back 15 minutes? There’s really only one good reason to say no to an idea: if it would put you in physical danger.
Despite what you learned as a kid, “yes” is also the answer to: Should you talk to strangers? (At least when culturally appropriate.) I sometimes like to set a goal — to talk to five random people a day, for example. Then I ask any dumb question that comes to mind. At a restaurant in Naples, I asked the Italian family at the table next to mine how their fritti misti appetizer was. They gave me the rest of the plate. I asked a fellow customer in a South Dakota gas station if there was any difference between the pot of coffee she was pouring and the one she wasn’t. It was fresher, she said. I doubt it was, and didn’t care anyway, but she turned out to be a fun Estonian exchange student with great stories of her journeys across America.
Great things also happen when your family or friends or friends of friends live in your destination. So seek out your Hungarian third cousins and the Vietnamese college roommate of your high school prom date for a meal or tea or some advice. No connections? Search for clubs or groups or professional organizations in your areas of interest. Surgeons may seek to tour a local hospital; journalists a newsroom; police officers a precinct. There’s no harm in trying. It just takes a quick search for accountants heading to Barbados to find an email for the I.C.A.B. (Institute of Chartered Accountants of Barbados, a real organization). The worst thing that could happen is nothing. Maybe you’ll score some great tips on beaches or night life or even make a friend. You don’t have to actually want to learn anything from the B.S.C. (Barcelona Sweater Club, a made-up organization). You’re just looking for a way to make a connection.
Seth Kugel, a former Frugal Traveler columnist, is the author of “Rediscovering Travel: A Guide for the Globally Curious” (Norton), published on Nov. 13.
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