A strange feeling came over me as I perused an exhibition about artificial intelligence at the MIT Museum in Cambridge, Mass., recently. The unsettled sensation derived not from the video of Richard Nixon giving a speech he never gave or even from the simulation of an AI-guided jet fighter in combat. Instead, my mind whirled as I realized that, in this show all about the history, promise and peril of artificial intelligence, I was as much exhibit as observer.

Inspired by recent headlines about Google’s new AI tool, Gemini, and its ability to “build an entire vacation itinerary” in seconds, I used a Memorial Day weekend trip to Boston to test the possibility. I was surely not the only visitor being guided by AI—especially at this particular exhibit. According to a 2024 study by MMGY Global, a travel marketing agency, 31% of “active leisure travelers” have used AI for travel planning.

To better understand the capabilities of AI, I used two of the most popular services, OpenAI’s ChatGPT and Google’s Gemini . I chose ChatGPT because of its ubiquity and because the online travel agency Kayak built a plug-in for it; and Gemini for similar booking capabilities, plus its ability to generate maps and even extract useful information from my emails. I signed up for the paid tiers for both (Gemini Advanced and GPT-4o) to access the latest models.

I started with a simple prompt: “Help me plan a weekend trip to Boston from New York City,” adding that “I want to stay in a cool, inexpensive hotel.” For getting to Boston, Gemini only suggested flights, while ChatGPT outlined the pros, cons and general pricing of traveling by plane, train, bus and car (I ended up opting for the bus). Both made similar hotel suggestions, overlapping when it came to the Revolution Hotel in Boston’s South End. Sleek and, at $194 a night, inexpensive given the holiday weekend, it proved a wise recommendation.

As I planned my weekend, two truths emerged: first, that even if AI can generate the bones of a trip in a matter of seconds, you’ll still probably make the actual booking the traditional way. Second, that the kind of inquiry I had made—based more on logistics than creativity—was just about the least effective way of getting the most out of AI when it comes to planning travel.

Generative AI’s abilities shine, I learned, when you make either much simpler or much more complex requests. You could just fire off a desire like “I want to see penguins,” said Matthias Keller, Kayak’s chief scientist and senior vice president for technology, and ChatGPT will round up destinations, while Kayak gathers real-time flight and hotel information.

As with Gemini, all of the information then spills out in an orderly, if inconsistently formatted stream of text, sometimes accompanied by images and links. Later this summer, I was told, Google plans to launch a dedicated travel interface for Gemini Advanced which will let you more easily modify and share trip plans, so your penguin-spotting trip doesn’t disappear into the endless scroll of your “conversations” with AI.

But don’t hesitate to be detailed—and pushy—in asking for what you want, says Amar Subramanya, Google’s vice president of engineering on Gemini. Last year, he and his wife asked Gemini—then called Bard—to help them plan a California beach trip with their sons. After they fed it a long account of everyone’s likes and dislikes, it returned an itinerary for Santa Barbara that was heavy on “standard, touristy destinations,” Subramanya said.

Unimpressed with the results, Subramanya’s wife followed up with “If we were actually living in Santa Barbara, which beach would we go to?” This prompted Gemini to suggest a lesser-known stretch of sand, and opened the door to conversations with the AI which ultimately yielded a far more interesting, off-the-beaten-path trip.

I, too, got better at asking questions as the trip went on. When seeking guidance for a walking tour, I wanted to venture beyond the established trails that appear in every guidebook’s first pages and so asked Gemini to design a custom route that included elements of the city’s Innovation Trail , including the MIT Museum, but also stops for ice cream and record shopping. It gave me a route on Google Maps to follow.

Searching for dinner, I asked both bots to recommend restaurants based on a list of my New York favorites. Both AIs recommended Pammy’s , which ChatGPT described to me as “bridging the gap between your love for inventive Italian and stylish New American cuisine.” Its lumache pasta with gochujang-spiked Bolognese sauce hit the spot.

Had I asked instead for buzzy, new restaurants, the AI might have struggled. For up-to-the-minute, on-the-ground intelligence, a travel agent or knowledgeable friend still has the upper hand. Humans also have something else AI lacks: conviction. Repeat a question to Gemini or ChatGPT, and you might get a different answer the second time, like you’re shaking the world’s smartest Magic 8 Ball. That said, do I think the technology, though young and occasionally wonky, will change the way we plan travel? Signs point to yes.