Nothing against relaxing on beachfront daybeds or doing the cathedral-monument-museum circuit, but for travelers like me (and, I’m guessing, like some of you) the ideal vacation is one that combines relaxation and sightseeing with unexpected finds down narrow streets, lively conversations with surprising locals and wrong exits leading to hidden treasures.
Alas, such experiences are not sold online. It takes good fortune to stumble across the Montana farm stand with the juiciest peaches imaginable, a Swedish farmer who invites you to his Beatles-loving friend’s home for music and whiskey, or the Albanian seaside restaurant owner who dares you to come back at 6 a.m. to fish for the next day’s catch.
Those are my serendipity-aided stories and you can’t have them, but it’s easy enough to create your own. Serendipity is essentially a synonym for good luck, but it’s hardly random. “The harder you work, the luckier you get,” golfers like to say. Good news for globe-trotters: No need to put in hours at the tourism range to lower your travel handicap. A few largely effortless adjustments can up your serendipity game.
Visit ‘em where they ain’t
You can’t force a local to chat, as I’ve found out on many an uncomfortable bus ride. But you can stack the odds in your favor by visiting countries, regions or cities where you don’t have to. My top travel axiom: The fewer visitors a place gets, the more eager locals are to talk with them. To put it another way, you’re unlikely to befriend a Parisian who lives a block from the Eiffel Tower. (Unless he’s got skin in the tourism game: souvenir sellers worldwide are more than happy to be chummy.)
Where crowds are sparse, or at least not Venice-level oppressive, locals are often just as curious about visitors as visitors are of them. So wherever you’re itching to go, consider alternatives that may not be as flashy, but have just as much to offer, minus the crowds. Sardinia over Tuscany; Kuélap, Peru, over Machu Picchu; Algeria over Morocco.
You can apply the same principle within a popular destination. As a New Yorker, I instinctively flee from sidewalk-clogging clumps of tourists in Midtown Manhattan. But across the East River in my culinarily blessed neighborhood of Jackson Heights, Queens, it’s a different story. When I recently spotted a youth group from the Midwest gawking at the South Asian shops and food stands on 74th Street, I practically pounced on them. Where are you all from? Why are you here? Where are you going next? How may I help?
Practice deliberate spontaneity
“My vacation days are so precious. I can’t risk something going wrong, so I plan everything”: This is a common lament of the annual-vacation-starved American adult.
Planning is crucial, I agree. But a tightly scheduled day does not preclude spontaneity. Consider your itinerary a rough draft, ready for modification if something piques your interest. I once abandoned a day trip to the Turkish city of Sanliurfa when I realized I was driving through pistachio orchards to get there and decided to turn off the highway and spend the day in a village seeking a farm tour. It worked.
You hardly need to risk a day, though. Imagine you’re off to lunch at a fancy place that got raves in your guidebook when, on the way there, you pass a spot humming with locals. Time to ditch your plans. Even if the chef at the new place is not Michelin-starred (or perhaps not even a chef), sometimes a simple meal you don’t know is coming is better than a fancy meal for which you have sky-high expectations.
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.
Follow NY Times Travel on Twitter, Instagram and Facebook. Get weekly updates from our Travel Dispatch newsletter, with tips on traveling smarter, destination coverage and photos from all over the world.