Dinner with a Tuscan nonna? A pin with an English artist? A cottage industry has sprung up to offer authentic experiences with local residences.

One day, when you’re lost in Manhattan, staring quizzically into the origami-like folds of a concierge’s city map, you might keep an eye out for a certain kind of New Yorker quietly watching you.

If you’re in my neighborhood, this person might be me. I live to give directions. Walking the city, I am constantly alert to any visual clues of Lost Tourist Syndrome. I am like a superhero with one tiny, extremely limited superpower: I can situate you on the grid, point out the nearest subway, and direct you from Dean & Deluca to the Uniqlo store. A lot of us want to help. Not because we’re exceptionally kindhearted, though thanks for thinking that. Nor are we members of that self-righteous breed of city folk who feel the need to impose our taste on the visitor. We like to help because it makes us feel like that most firmly dependable and indispensable urban dweller: the in-the-know insider. Perhaps it’s because I’m so often traveling and in need of the guidance and goodwill of local experts that I long to be one when I’m home.

We used to travel to see the sights: Indian palaces; Italian cathedrals; big game in Africa. For some places, it’s still sufficiently moving to simply stand near them, feel the power of their proximity (the Taj Mahal, say, or the stone men of Easter Island). But for much of the world, just looking isn’t enough. It’s not enough to sever ties with our own daily lives; we need to connect with others. We seek the real—to feel that we’ve been truly transported to a definite somewhere rather than the vague, dizzying nowhere of shuffling through airports. We’ve become collectors of people; we’re all locaphiles now.

The social side of travel is big business now, life imitating the Internet. Luxury travel can be isolating because of the natural distance between the way you see a place and the lives of the people there. So travel agents have enlisted the expertise of residents to show you around. Unfiltered access, connections, insight—these are the new value-added.

What is a local? Just living somewhere doesn’t qualify you for the job. Being a local requires more than knowing how to read a map (there’s an app for that). The kind of local we want to meet is someone with a take on a place, a story to tell, a passion or particular expertise—all linked to where we are. They’re the London cabbies of culture, the Baedekers of burger joints and best bartenders, the translators of foreign topography; they’re trivia nuts and social anthropologists, insightful old-timers and knowledgeable newcomers. They’re the kind of people you’d be happy to fall into casual conversation with anywhere you go. And, increasingly, more than all the museums and points of historical interest in all the guidebooks in the world—they’re why you traveled there in the first place.

Think about the boxes or hard drives full of all the travel pictures you’ve ever taken. How often do you look at that snapshot of the corner of the Colosseum? Or the one that captured the full splendor of the breakfast spread at Rio’s Copacabana Palace Hotel? We can get the postcard images anywhere, it’s the human sentiment of the handwriting on the other side we miss. The pictures I care about most, the ones I linger over, have as their subjects not places but people. Friends, family, strangers who’ve wandered into my line of sight long enough to merit remembering. As nice as it is to share travel memories with the people we set out with, there’s a special feeling reserved for the ones we met along the way—a combination of the excitement of something new, curiosity undimmed by extended contact, and relief at not being lost in an unfamiliar place, or not being stranded alone with a dull book at the restaurant bar.

I’ll sometimes see visitors in New York peering into guidebooks describing my neighborhood in Japanese or Spanish and I envy their dislocation, their broken circadian rhythms that allow them to fall into this new tempo. I wonder who they’ll meet here and how their perception of the city will be shaped and altered by those encounters. And again invariably I’ll think of my own wanderings and the locals I met who gave me my bearings. The chefs I befriended in Cape Town who took me for a beach braai on the coast. A.T. in Mumbai, who one night drove me to an after-hours kebab stand where we ate grilled lamb and roomali roti delivered to the hood of his car; on another night he took me for a straight-razor shave at his barbershop in Malabar Hill. Throw the dart at the map and similar interactions come into focus: the mother-and-daughter cheese makers in Tasmania who invited me to dinner at their house; the inspired photographer turned hotelier who led me on a surreal bike ride around the tiny Swedish island of Furillen; Uncle Felix, an aging gentleman of undisclosed occupation who took me on a long tour of Hong Kong bars where everyone knew his name and nobody would let him pay for a drink. What makes these connections so magical is the extent to which they are unforeseen, unrehearsed, unrepeatable. The platonic one-night stands of the committed traveler. The best travel planning is to leave yourself open to a kind of unplannable serendipity, to be always, as E. B. White once counseled anyone thinking of living in New York, “willing to be lucky.”

Authenticity is to the locaphile what pasture-raised beef is to the locavore. But what happens when we all want these authentic experiences—and we need them to happen in the three days we’ve got for the trip? What happens is that a certain segment of the travel industry adapts to our evolving tastes and desires and plays matchmaker between discerning client and well-chosen local. Is it engineered serendipity? Maybe, but it works. Those of us who tend to go our own way and hope for the best might be surprised at how sophisticated and frankly envy-inducing the kinds of matchups offered by specialty tour operators and high-end personal concierge services can be. Pure Entertainment Group, based in Montreal, will organize such disparate diversions as chess tourneys against a grand master player in Glasgow (followed by dinner to discuss the game), or a personal shoemaking class with a member of the Singaporean Peranakan Nyonya, or a night of clubbing in L.A. with connected partygoers who know their velvet ropes. “We have friends who live like rock stars in L.A. 24/7, and with us, you’ll live that life, too,” says Teneisha Collins, PR and advertising manager of Pure.

In Italy you can arrange to have a meal with an actual Italian grandmother. And there are matchmaking services in Amsterdam and Paris to put you in touch with the natives. Anne Morgan Scully, the president of McCabe World Travel, calls the kind of in-depth itineraries she pulls together “pillow-to-pillow experiences,” meaning she’ll curate your day from when you wake to when you fall asleep. In between, she’ll send you off to meet with a sculptor in Florence or a professor of Asian studies in Hanoi. “You can’t Google these people,” Scully says of the kinds of intimate, personalized interactions she brokers. “This professor isn’t going to be on the Internet. It’s based on relationships.”

When money (as opposed to just anecdotes or rounds of beer) is changing hands there’s always the chance that these relationships can become more rehearsed, more generic. “We introduce our clients to so many fun-loving people that after a while everyone forgets they’re not old friends,” says Jón Kári Hilmarsson, who runs Nightlife Friend, a service he founded to help visitors navigate Reykjavík’s bustling club and bar scene. Cemantha Crain of AuthentEscapes points out that “the individuals we’re connecting travelers with don’t have to open their doors and welcome us. It has to be more than money that motivates, and it is. So it’s not just a matter of a wire transfer, but really creating meaningful experiences that reward parties on both sides of the ‘transaction.’ ” Certainly the level of access Crain can supply is rewarding for those who can afford it and delight at the attendant bragging rights: “We chartered the Christina O with Celia Sandys, who’d sailed on board with her grandfather Winston Churchill in her youth,” she says. “Our guests stay at the Ferragamo family’s private villa at Il Borro. Salvatore will personally show them around the estate and the wine production while his wife, Tini, will take them on whatever kind of shopping tour they may be interested in. And Jehan Sadat welcomes travelers into her home on the Nile to see pictures and hear about her life and her late husband, Anwar.”

Next time you’re turned around in New York, ask me for directions. I don’t have a yacht or an in with the Ferragamos but I could probably lead you to a good banh mi or bring you to my favorite hole-in-the-wall. So don’t be a stranger.

Adam Sachs is a T+L contributing editor.

AuthentEscapes Cook in Beijing with the grandson of Chairman Mao’s personal chef or taste champagne with Olivier Krug in Reims, France. authentescapes.com

Dine with the Dutch Eat with locals in Holland. dinewiththedutch.com.

Home Food Dine in the homes of real Italian nonnas. homefood.it.

McCabe World Travel Customized itineraries from arts tours of Paris to visiting monks in Thailand. mccabeworld.com.

Meeting the French Programs like “Meet the Parisians at Work” and “Dinner with French Hosts.” meetingthefrench.com.

Nightlife Friend Meet up with nightclubbing insiders in Reykjavík, Oslo, Copenhagen, or Barcelona. nightlifefriend.is.

Posh Travel Customized itineraries including private homestays in Kyoto and visits to Masai villages in Kenya. poshtravel.com.

Pure Entertainment Group Bespoke concierge experiences from L.A. to Scotland. purentonline.com.

7tm A neighborhood coalition that offers shopping tours by stylists who live or work in this burgeoning design district in Vienna. 7tm.at.