You Can Now ‘Ask Maps’ For Hyper

I am not like other men. I like to ask for directions. Some might call me an unabashed neanderthal, but I adhere to a city’s rhythm, not the algorithm. I let my legs and eyes and nose lead me. In a new place, I have historically enjoyed any excuse to embrace my interrogative prerogative and engage with locals by asking for guidance—to a hip café, to an off-the-beaten-path bar, to the nearest restroom. As a try-lingual chap, a wannabe polyglot in it for the plot, I can attest to the fact that my interpersonal gregariousness has facilitated several memorable side-street side quests—during a college Russian program in St. Petersburg (flirtation and fluency), a day trip to Tangier (an unexpected guided tour), and a ride on Xi’an’s metro (a hand-crocheted rose for my daughter). Last year, a young couple ferried my family, suitcases and all, through Tokyo’s Cat Street to help us arrive on time for our reservation at a hard-to-locate pig café. When I offered a tip, they recoiled and waved their hands with such urgency that I looked down to see if I was wielding a knife. Human kindness—that was the exchange, I remembered. My standard approach to travel seems at odds with Google’s Ask Maps, its sexy new conversational AI feature, powered by Gemini, that can chart out clean travel itineraries based on crowd-sourced rankings and efficient routes with waypoints that adhere to your specified preferences—or even predict them. That travelers are increasingly turning to AI chatbots like Open.AI’s ChatGPT, Anthropic’s Claude, and Perplexity AI to build out itineraries and get them to the best local greasy spoon, ice-cream parlor, and coffee shop, is old news. Ask Maps, however is the first integration of its kind, allowing travelers to ask such specific queries as “My phone is dying—where can I charge it without having to wait in a long line for coffee?” or “Is there a public tennis court with lights on that I can play at tonight?” without ever leaving the Google Maps app. The convenience is undeniable, but what do we lose when we do away with those random travel moments of yore? Are we sacrificing the joys of spontaneity and discoverability by relying on AI? Vicente Abarca Del Rio, managing partner of Muletek, a global eSIM store, laments what’s missed with an over-reliance on technology. “Why do we travel?” he says. “Simply to follow the little line traced by our map, oblivious to the life unfolding around us?" Traveling with an element of anything-could-happen uncertainty puts us in a liminal state. With this unfamiliarity, we’re less sure of our footing. Of course, there’s something infantilizing, even embarrassing about being lost. We’re helpless, at the whims of strangers. But it’s also an invigorating contrast to the pre-charted course that’s become de rigueur. A chance to grow and learn and immerse ourselves to the experience. According to Andrey Meshcheryakov, head of practice at Recombinators, a management consulting firm that specializes in business innovation, Ask Maps “effectively de-risks the travel experience by eliminating the friction of human error and language barriers.” “While this utopian technological leap maximizes utility, it threatens the serendipity engine that traditional travel provided,” he adds. Tech, against the age-old adage, is prioritizing the destination over the journey. “Those small moments of asking for directions used to carry vulnerability,” says Seden Dogan, an assistant professor at the University of South Florida School of Hospitality and Tourism Management in Tampa whose research focuses on the emergence of AI technologies in travel. “The interactions give travel a certain texture that you don’t plan for, and things become smoother and more predictable with AI.” Dogan says discovery might still happen but feels increasingly curated. “I would not say we lose travel’s magic, but we are definitely shifting from organic, human-driven moments to more personalized, algorithm-driven ones,” she adds. As Jen Young, co-founder and CMO at Outdoorsy put it, “we are trading a bit of soul for a smoother interface.” Me, myself, and AI I wanted to explore these considerations by testing out Ask Maps against my Luddite sensibilities. A road trip from New York City, where I live, to my hometown, Princeton, New Jersey, would serve as an ideal proving ground. After all, I know the town and environs so well, and though I return periodically, I’ve been away for 18 years, almost half my life. Businesses have closed and opened—new gems lie in wait, as do unanticipated booby traps. Though this town, which predates the American Revolution, evolves at a glacial pace, evolve it does nonetheless. I was open to new discoveries. So with my wife, Tiffan, and daughter, Odella, in tow, we set off on an Urken family road trip. A cute little get-away to my old stomping grounds with the help of AI—what could go wrong? We left the Upper West Side and on the way to Princeton planned to stop, per Odella’s request, at Milburn’s South Mountain Fairy Trail, a half-mile hiking path dotted with intricately decorated mini fairy houses with acorn chairs and moss-covered roofs. Ask Maps initially misheard my request as “ferry trail” even after an overenunciated second attempt but still managed to land on the desired destination, along with parking recommendations, details on the experience, and the weather report. It also gave me an option to save fuel with route suggestions based on my engine type. I tend to use my car’s built-in navigation or the Apple Maps app, and though I disagreed with the turns Ask Maps guided me toward to get from my neighborhood to the Lincoln Tunnel—I know a new sneaky detour that gets me on the West Side Highway and avoids congestion—and got out of the city and on the right path just fine, my way. There’s something formulaic or unsurprising about travel with AI tools, according to Edita Sgovio, a vice president at luxury travel company Kensington. “Asking for directions often opens the door to much more: local recommendations, personal stories, even invitations to experiences you would never have found otherwise,” she says. Travel’s beauty can hinge on wrong or unexpected turns. In the car, those wrong turns are less romantic. I noticed the Ask Maps interface switched orientation and instead of allowing me to view my car on the bottom of the screen progressing on a straight path vertically, I found the orientation shifted to a side view that threw me off. I ended up erroneously taking a turn that sent me toward Staten Island. My wife was truly, positively thrilled. If you are looking for a slow, methodical way for you to remove your soul from your body, I recommend getting lost on the Jersey Turnpike. In the Garden State, we don’t have many legal U-turns. We have jug handles. Back on the highway as I recalibrated, I encountered our state bird—no, not the Eastern Goldfinch but one that’s more commonly spotted as a flipped middle finger extended from a lowered window. Once my family and I got back on track and arrived after a scenic detour of the Goethals Bridge, experienced hikers in all the gear pointed us, old-school style, to the head of the fairy trail. A dad from the area and I riffed on the likelihood of spotting fairies, performing for the kids listening. After we thoroughly enjoyed the fairytale magic, it was time for Ask Maps to direct us to a Chili’s on the way to our hotel in Princeton. Tiffan is from Oklahoma and sometimes has a hankering for chain-restaurant queso. I find this somewhat endearing, even if it doesn’t prevent me from judging her and participating begrudgingly. Happy wife, happy life. From the hotel the next morning, I consulted Ask Maps for an authentic local breakfast place. It hit the nail on the head, recommending P.J.’s Pancake House, where we typically like to go for a hearty breakfast in town. Though its rec was on point, Ask Maps also threw out a tempting new opening I had not yet heard about: Delizioso Bakery + Kitchen, “a cozy neighborhood gem where visitors praise the outstanding omelette and freshly baked artisan bread.” It also suggested the “Green Eggs and Ham” crepe at Jammin’ Crepes, a menu item that was not on my radar but which Odella may be interested in on a future trip. Similarly, when I asked for a coffee shop, Ask Maps recommended Small World Coffee, a Princeton institution since 1993 “known for its vibrant, artsy atmosphere,” the sort of place where I’d bring my laptop or a book. But it also recommended Sakrid Coffee Roasters, a tempting new “modern, light-filled space” that serves “single-origin espressos.” Ask Maps also told me that Princeton now has a Maman. Even for a native son of the village like myself, the app could surface some important information previously unbeknownst to me. At my fingertips, I had an embarrassment of information instead of my usual unalloyed embarrassment. In this information-gathering quest, I certainly saved time by not having to rely on asking locals about new openings or pounding the pavement myself to happen upon new discoveries. But I couldn’t shake the fear that I was leaving behind a fundamental element of travel in the process. “We’re not losing directions,” says Matas Cenys, the Vilnius-based head of product at Saily, a travel eSim app. “We’re losing permission to be lost.” That used to be a core part of travel. You’d miss a turn, ask someone for help, end up in a conversation, sometimes even in the wrong place and that’s where stories came from. “AI removes that layer entirely,” Cenys says. “You move through a city without ever needing it. The risk isn’t that travel becomes easier, it’s that it becomes too polished to leave an impression. When everything works perfectly, nothing really stands out.” The key question is whether travelers still leave space for spontaneity, even when everything can be optimized. The pantomimes, gestures, faces. The humiliation. The awkward laughs. The hands held to the heart. The humanness. “Those are the kinds of experiences that rarely happen when you’re just following a blue dot on a screen,” Cenys says. Bridging the gap between old-school and new age Annalisa Nash Fernandez, who runs business and strategy firm Because Culture in Stamford, Connecticut and is a self-described “absolute savage on Google Maps” who pins recs immediately, thinks AI hasn’t entirely obviated the need to interact with locals. It just changes the premise and improves the connection. She notes that the chatbot style function Ask Maps allows you to go beyond surface-level internet advice and viral fads by asking things like "Is there a jazz club within walking distance with live music tonight?" or “find me a traditional tea house nearby that doesn't require a reservation." You can point your camera at a building using Google Lens and ask, “What's the vibe inside?” and get an actual answer drawn from street-level data and reviews. The Gemini layer connects to your calendar and can brief you on a neighborhood before you step off the train. “Know Before You Go” pulls structured review content so you're not walking into a situation blind. (That said, such information could preempt a traveler from trying out a venue that would actually suit their tastes, leading them to write off an experience before they have the opportunity to dive deeper into the local culture and see how it fits.) Net-net, though, maybe there’s something to be gained from avoiding the awkward perfunctory inquiry with locals. According to Nash Fernandez, the technology doesn’t remove the need for an interaction with real people, she postulates; it just changes the form it takes. “I’ve had richer conversations with locals because I wasn't burning the entire interaction on, ‘Where is the pharmacy?’ Nash Fernandez says. “That's an interaction upgrade.” Rather than asking for one opinion—a sort of Schrodinger’s Cat of reliability—you can crowdsource a collective consensus. “Technology has actually made the deeper layers of culture more accessible,” she says, harnessing millions of places and opinions. “It’s discovery at a scale that was never possible before.” Jaroslaw Grabczak, head of commercial product at eSky Group online travel agency, cites AI’s shortening of travel’s discovery phase a “double-edged sword.” “You get exactly what you said you wanted, but you miss out on everything you didn't know you needed,” he says. “The best use of AI in travel is not replacing the human layer, but compressing the logistics so that the human layer has more room to breathe.” Perhaps if we can eliminate some of the headache of trouble-shooting, we can be more present and have deeper interactions with the cities we’re discovering and the locals we meet. Asking for directions and local recommendations has long served as a icebreaker, an excuse to talk to a stranger with the putative purpose of getting to your destination and the potential (secretly desired) bonus of a memorable interaction that also delivers authenticity and kindness. But with our optimized routes obviating that need, we will have to make a concerted effort to remember to look up from our phones and seek out more meaningful human connection. “If you don’t make a conscious choice to engage, those human moments simply fade away,” says Luciano Armanasco, the Lombardy-based founder and tour leader of Our Dolce Vita. “The real danger isn’t that AI means you won’t get lost. It’s that it reduces the need to connect.” As we neared the end of our weekend away, Odella wanted ice cream while Tiffan shopped. Her main criterion: the availability of a high-quality strawberry flavor. My prompt for Ask Maps: “Can you navigate me to an ice cream shop in Princeton?” There are three main ice cream shops in town, but it told me to go to The Bent Spoon, “a local favorite known for its inventive, organic flavors” before noting it was just a short trip from my current location. It had 1,590 reviews and a 4.7 rating—boosting it on the algorithm. But it would have taken 10 minutes to walk there. Halo Pub, with 1,219 reviews and a 4.5 rating, was another option with “a rustic atmosphere and rich ice cream made with milk from its own local dairy.” But that was also quite a distance from where we were. Ask Maps also proposed Thomas Sweet, but with only 737 reviews and a 4.5 rating, it was presented as a less desirable option. But as a person with a beating heart and the ability to fog a mirror, I could see Thomas Sweet was mere steps from us and knew it would actually best suit my daughter’s taste buds. The ice cream might have fallen short of five stars according to Ask Maps, but Odella ranked her strawberry ice cream with rainbow sprinkles 100/10. On the way out, I also ran into a dear friend from middle school who I wouldn’t have seen had I followed AI. James, a born-and-bred local, prefers Thomas Sweet. One reminder from this experience: even though the recommendations from our tech overlords feel authoritative, we can iterate on the prescribed itineraries of our own volition. We have the human critical thinking skills to go off-road from what the algorithm tell us to do and filter its suggestions based on our own proclivities. “I get why people worry that [AI] takes away some of the magic,” says Sean Finelli, co-founder and CEO of The Tour Guy in Sarasota, Florida. “But honestly, I think it just changes where that magic shows up.” “Ultimately, I think AI can help you get to the door and more easily, but it can’t replace what happens once you walk through it,” he says. “That part still comes down to the traveler—being curious, open, willing to engage. It's a mindset of the individual. And that’s not something technology is going to replicate, at least not anytime soon.”