A “Friday evening matinee?” To quote the Gershwins, it ain’t necessarily so. But that’s how modern artificial intelligence suggested I hit Broadway.

When I was asked to see what A.I. gets right and wrong about visiting New York City, I was deeply curious and felt well qualified for the assignment — I’ve been a resident of Manhattan since 1989, a frequent city tour guide for friends and family, and a journalist who has written about technology (including chatbots) since the 1990s.

I sampled several A.I.-planner sites with the same vacation request: Create an itinerary for a trip for two people to New York City from April 17 to 20 that suggests an affordable hotel (less than $250 a night) in the middle of the city, several iconic landmarks or museums, a matinee performance of an award-winning Broadway show and a great pizza stop. I asked for directions for accessible ways to get to each place from the hotel, and then made additional requests for suggestions if children were coming along.

While most of the sites offered many of the same classic New York spots, like the Museum of Modern Art, the user experience varied. (Note that all the sampled sites use OpenAI’s software in some way and The Times has an active copyright-infringement lawsuit against OpenAI.) If you are new to the world of A.I. travel planners, here are a few that may appeal to certain types of human travel planners.

If you want a friendly interface

With its energetic home page full of photos and features, Mindtrip (free) felt like the most welcoming A.I. planner for a newcomer. Its initial itinerary hit most of the top tourist stops, like the Statue of Liberty, the Metropolitan Museum of Art and Central Park, with links to the sites’ suggested highlights. Mindtrip also suggested the Pod 51 hotel on East 51st Street (about $303 a night), which is a great location, but rooms in the Pod chain aim for “chic minimalist,” which may not be for everyone, particularly families.

The Good: Manhattan sights tends to dominate the list, but Mindtrip suggested going over the Brooklyn Bridge for photo ops and Grimaldi’s Pizza — so points for getting to a second borough.

The Bad: The schedule for the third day suggested visiting the Statue of Liberty and the Empire State Building in the morning — and then going to the matinee of “Hamilton.” That seemed unrealistic with timed tours and travel across the city, especially since the Saturday matinee starts at 1 p.m. Swapping the suggested stroll around Rockefeller Center and Times Square from another day in the itinerary made more logistical sense.

The Unexpected: When asked for a “hidden gem” to visit, it proposed the Tenement Museum, which reveals a century of New York City history through the experiences of its immigrants.

If you require details up front

Vacay, (free; $10 a month, for premium plan) another web-based chatbot and planner, had a more text-heavy but clean interface and suggested several of the same city landmarks with relevant links. For those unsure about how to ask for information, the site has a helpful best practices guide for writing A.I. prompts to get the best results. Vacay’s premium plan, designed for frequent travelers, offers more enhanced A.I. models for more specific recommendations, tech support and advice on planning themed vacations.

The Good: While it lacked its own maps in the chat window, Vacay’s itinerary planner had more precise advice, not just suggesting Central Park, but recommending Bethesda Terrace and Strawberry Fields within it. And it also named specific bus and subway lines to get to the destinations without requiring a separate request, based on the location of its suggested Pod 39 hotel on East 39th Street (about $290 a night). You can download your chat transcripts, even in the free plan.

The Bad: The Vacay bot suggested a “Friday evening matinee” of a Broadway show.

The Unexpected: The site advised visiting Top of the Rock for city views, which allows you to include the Empire State Building in your photos, so points for considering the skyline-selfie experience.

If ChatGPT is used for everything

The popular and pioneering ChatGPT (free; paid plans start at $20 a month for advanced features, like the new Deep Research tool) also recommended staying at the Pod 51 hotel; the Pod people have clearly had an influence on the Bot people.

The Good: ChatGPT made sensible plans for multiple activities in the same part of the city, like grouping a morning visit to the Statue of Liberty and Ellis Island with an afternoon stop at the 9/11 Memorial & Museum.

The Bad: ChatGPT also suggested a Friday matinee for several Broadway shows, despite the fact that Friday is not a matinee day for any of them. Some predicted walking times were impractical — hoofing it from the theater district to Joe’s Pizza on Carmine Street takes much longer than seven minutes; perhaps it really meant the Joe’s near Broadway and 40th Street.

The Unexpected: A stroll on the High Line and a visit to Chelsea Market popped up as a suggestion. Which come to think of it, would be very nice on a spring day.

If a trusted travel site is vital

If you’d prefer to stick with a familiar brand, 25-year-old Tripadvisor is among those offering A.I.-planning help. To build a trip, you just answer a few questions about what you want to do and Tripadvisor presents a screen full of menu choices. Click the desirable options and the site builds a trip schedule. Among the hotel suggestions: the Pod Times Square on West 42nd Street (around $259 a night), leading me to believe if you have “affordable hotel” in your N.Y.C. request, travelbots will suggest a Pod.

The Good: Tripadvisor had the best ideas for children, including a stop at the Hayden Planetarium and the Wonderland-inspired Alice’s Tea Cup restaurant.

The Bad: The site suggested the Alice’s location on the east side of Central Park instead of the one near the planetarium on the west side.

The Unexpected: Tripadvisor, which has a huge repository of user-generated reviews, switched up some of the pizza recommendations to include Don Antonio and Capizzi along with the usual John’s and Joe’s stops.

Tripadvisor also had the most cheerful disclaimer: “A.I. isn’t perfect, but it’ll help you hit the ground running.”

Every A.I. travel-planner tested here (along with others out there, including Layla, Wonderplan and the mobile-friendly GuideGeek) warn you that the information you get from them may not be correct. Take this to heart and double-check all of it.

Another tip: If you’ve never used an A.I. travel planner before, keep in mind that asking for everything in one big query can lead to some muddled responses. Start with the basic outline of the trip, like finding a hotel in a certain area for specific dates, and then ask about local attractions, transit directions, restaurant recommendations and other information in subsequent requests to build out your itinerary.

While A.I. planners are still mostly used for research and planning, autonomous A.I. agents like OpenAI’s Operator could soon be booking your trips as well, and you’ll really want to make sure that itinerary is correct.

Follow New York Times Travel on Instagram and sign up for our Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2025.