“Matiny on a Friday night?” To quote Gershwins, that's not necessarily the case. But that's how modern artificial intelligence suggested I'd hit Broadway.
When asked to see what was right or wrong about visiting New York City, I felt deeply interested and suited to the challenges – I have been a Manhattan resident since 1989, a frequent city tour guide for friends and family, and a journalist who has written technology (including chatbots) since the 1990s.
I sampled several AI-Planner sites with the same vacation request: I will create an itinerary for two people's trips to New York from April 17th to 20th. I asked for directions for an accessible way to reach each location from the hotel, then made additional requests for suggestions if the kids came.
Most sites offered many of the same classic New York spots, like the Museum of Modern Art, but the user experience was varied. (Please note that all sampled sites use Openai's software in some way, and Times has filed an aggressive copyright infringement lawsuit against Openai.) If you're new to the world of AI travel planners, there are a few things that could appeal to certain types of human travel planners.
If you want a friendly interface
With an energetic homepage filled with photos and features, MindTrip (free) felt like the most welcome AI planner for newcomers. That first itinerary hit most of the top tourist stops like Statue of Liberty, Metropolitan Museum of Art and Central Park, with a highlight where links to the site were proposed. Mind Trip also proposed a Pod 51 hotel on East 51st Street (approx. $303 per night), a great place, but the pod chain rooms aim to be “chic minimalist”.
Good: Manhattan tourist spots tend to dominate the list, but Mind Trip suggested crossing the Brooklyn Bridge for photography and Grimaldi's pizza.
Bad: The third day schedule suggested visiting the Statue of Liberty and the Imperial State buildings in the morning, and then going to the matinee of “Hamilton”. It seemed unrealistic on timing tours and on trips around town. Matiny, especially on Saturday, started at 1pm and swiveled on the itinerary to walk around Rockefeller Center and Times Square from another day, making it more logistical significance.
Unexpected: When asked to visit “hidden gems,” it proposed a tenement museum that reveals the century of New York City's history through immigration experience.
If you need more details in advance
Vacay (free; $10 a month for a premium plan) Another web-based chatbot and planner proposed some of the same city landmarks with more textual but cleaner interfaces and associated links. For those who are unsure about how to request information, this site has a useful best practice guide to writing AI prompts for the best results. Designed for frequent travelers, Vacay's premium plans offer a more enhanced AI model for more specific recommendations, technical support, and thematically themed vacation planning advice.
Good: Although there was no map of its own in the chat window, Vacay itinerary planners received more accurate advice not only suggesting Central Park, but also recommending Bethesda Terrace and Strawberry Fields among them. We also got there to reach our destination without the need for another request, based on the recommended Pod 39 Hotel on East 39th Street (approximately $290 per night) with a specific bus and subway line. You can download chat transcripts even if it's a free plan.
Bad: Vacay Bot proposed the Broadway show's “Friday Night Matinee.”
Unexpected: This site advised to visit the rock summit for an urban view that could include Empire State buildings in the photo, so it's a point to consider a self-experience of the skyline.
If ChatGpt is used for everything
Popular and pioneering ChatGpt (free; paid plans start at $20 a month with advanced features such as the new Deep Research Tool) are also recommended to stay at the PoD 51 hotel. The people at the pod have clearly influenced the people at the bot.
Good: ChatGpt has made wise plans for multiple activities in the same part of the city, including grouping together statues of freedom and morning visits to Ellis Island at an afternoon stop at the 9/11 Memorial & Museum.
Bad: ChatGpt proposed Friday matinees for several Broadway shows despite the fact that Friday is not a matinee day for either of them. The predicted walking time is predicted to be unrealistic. It takes more than seven minutes to hooves on Joe's pizza on Carmine Street from the Theatre District. Perhaps it really meant Broadway and 40th Avenue near Joe.
Unexpected: A walk along the High Line and a visit to Chelsea Market appeared as a suggestion. Considering that, it would be a great spring day.
If a reliable travel site is essential
If you want to stick to a familiar brand, the 25-year-old TripAdvisor is one of the things that offers Ai-Planning Help. To build your trip, just answer a few questions about what you want to do, and TripAdvisor will present you with a screen full of menu choices. Click on the desired option and the site will create a travel schedule. Some of the hotel proposals include Pod Times Square on West 42nd Street ($259 per night), and if you have a “affordable hotel” on your NYC request, you'll be convinced Travelbots will offer a pod.
Good: TripAdvisor had the best ideas for kids, including stopping at Alice's teacup restaurant inspired by the Hayden Planetarium and Wonderland.
Bad: This site suggested Alice's location on the east side of Central Park, not something near the planetarium on the west.
Unexpected: With a huge repository of user-generated reviews, TripAdvisor has switched some of its pizza recommendations, including Don Antonio and Capizzi, along with the usual Johns and Joe stops.
TripAdvisor also had the most hilarious disclaimer. “AI is not perfect, but it helps you run to the ground.”
All the AI travel planners we tested here (along with others, like Layla, Wonderplan, Mobile-friendly Guidegeek, etc.) warn that the information we get from them may not be correct. Keep this in mind and double-check everything.
Another tip: If you've never used an AI travel planner before, keep in mind that requesting everything in one big query can lead to some confusing responses. Starting with a basic overview of your trip, such as finding a hotel in a specific area for a specific date, and asking for local attractions, transit instructions, restaurant recommendations and other information in subsequent requests to build your itinerary.
AI planners are still used for research and planning, but autonomous AI agents like Openai operators can also book your trip quickly. And you'll really want to make sure your itinerary is correct.
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