Trip planning can feel like a slog, full of chores that artificial intelligence chatbots should be able to speed up. The technology was still bad a couple of years ago. Is it up to the task yet?
As the personal tech columnist for The New York Times and a frequent traveler, I was eager to test whether A.I. could streamline the planning process, which typically takes me hours of reading travel guides and plugging information into notepads and spreadsheets.
I was mapping out the details for a 14-day trip last month to Taiwan and Hong Kong with my wife and our 20-month-old daughter, and I also wanted help planning an upcoming summer vacation to Hawaii.
I had plenty of options, including piecemeal apps that use A.I. to book flights as well as popular chatbots like ChatGPT and Claude. Because I’ve found that it’s usually easier to stick with a single app rather than toggle between a bunch, I decided to focus on one.
I chose Google’s Gemini chatbot app for two reasons. First, unlike the other chatbots, Gemini was already hooked into Google’s extensive resources for finding flights and places to eat, and second, I wanted to test it alongside Ask Maps, a new A.I. feature built into the Google Maps app.
The good news: The Gemini chatbot, which was recently improved to give more bespoke responses based on personal data, and Ask Maps were a potent combination that saved me time, especially with researching restaurants and tourist attractions. I spent only about 30 minutes planning my activities in Taiwan and Hong Kong.
The bad news: Gemini occasionally made mistakes — like forgetting to include underwear on my packing list — so there was manual work I had to do. Despite the imperfections, I generally recommend using Gemini as a virtual travel agent for help with planning your next trip.
Here’s what I learned.
A Chatbot With Connections
Gemini is better equipped for trip planning than other A.I. chatbots because it has direct access to Google Flights and Google Hotels for looking up airfare and lodging. I’m also a firm believer that the joys of packing light also apply to travel apps, and Gemini is essentially a Swiss Army knife.
Google also recently released two new A.I. features that are useful for trip planning: Personalized Intelligence, an option that users can activate inside the settings of the Gemini app, and Ask Maps, a button that recently began appearing inside the Google Maps app.
With Personalized Intelligence, Gemini can pull data from multiple Google services, including Gmail, Calendar and your search history, to come up with its responses. In other words, if you ask Gemini, “Recommend some restaurants near the hotel when I arrive,” it knows where you’re staying and approximately when you’ll get there based on information found in your email. I liked how I could quickly and efficiently get help from Gemini without having to remind it about the details of my trip.
If you, like me, are concerned about giving Gemini access to so much personal data, just create a Gmail account you use exclusively for travel, and activate Personalized Intelligence on only that account.
In Google Maps, the Ask Maps button lets you ask conversational questions like “Can you explain Tokyo’s train system?” or “Is there a stroller-friendly route to the space museum?” and get Gemini-powered responses based on where you are.
Lists With a Few Hiccups
For my trip to Taiwan and Hong Kong, I used Gemini mostly for preparation and research, including generating packing and to-do lists.
“Generate a packing list for me and a 20-month-old toddler,” I wrote. (My wife used her own packing list.) The chatbot produced a handy lineup that included diapers, medication, noise-canceling earphones and a power adapter. However, the bot neglected to add socks and underwear to the packing list for me, a 41-year-old who has never experimented with nudism. I added those two items manually.
I also asked Gemini to generate a list of important tasks to finish before the trip, and it came up with a useful summary, which included checking the validity of the family’s passports and researching options for cell service abroad, another task I assigned to the chatbot. It recommended a cheap data plan that worked in both Taiwan and Hong Kong — perfect.
When I was happy with the lists, I asked Gemini to copy them to a notepad for later use. The lists showed up inside Keep, Google’s notes app, with boxes to check off when I completed the tasks.
A Knack for Planning
Gemini shone in sketching out rough itineraries without me needing to do much. I asked it to generate a daily plan of activities, and because Gemini already had access to my emailed airfare and hotel reservations, and because it was aware that I was traveling with a toddler, it came up with an outline of family-friendly activities for each day. I asked Gemini to save the itinerary as a note in Keep.
When my family and I followed the itinerary in Taiwan and Hong Kong, we had a good time — it even accounted for jet lag and taking short breaks with a toddler. For instance, Gemini recommended taking it easy on the first day in Taiwan by walking to Daan Forest Park and Yong Kang Street, an area nearby known for its restaurants. We enjoyed our stroll and shared a bowl of delicious mango shaved ice before returning to the hotel.
Mixed Success in Real Time
While Gemini excelled at researching ideas in advance, it began to stumble when I needed help in real time. For instance, when I arrived in Hong Kong, I asked it to recommend restaurants near my hotel, but it showed restaurants near my previous hotel, in Taiwan. Google said Personalized Intelligence was still unfinished, and that mixing up timelines was a known issue that it was working to improve.
Fortunately, the Ask Maps feature handled these types of requests with gusto. On a rainy day in Hong Kong, I opened Google Maps, tapped the “Ask Maps” button and typed, “It’s rainy. Find activities to do with a toddler nearby.” The app suggested a visit to the science museum and gave me directions to walk there in 10 minutes. My daughter, who is not easily entertained, squealed with delight at the robotic dinosaurs.
Similarly, when I was standing on a street in a busy shopping district, I typed, “Narrow down the restaurants on this street with good reviews.” Ask Maps immediately showed me a handful of top-rated restaurants, including a shop that specialized in pan-fried pork buns.
I brought them back to our hotel, and the buns got rave reviews, including from a hangry toddler.
Smarter, Not Just Cheaper, Flights
In my tests, I found that asking Gemini to look up flight and hotel options worked better than manually browsing travel booking sites the old-school way. That’s because Gemini went beyond just prioritizing prices to summarize the best options based on my personal situation.
For example, for my upcoming trip to Hawaii, I asked Gemini to look up the best flight deals in July. Gemini pulled information from Google Flights to show that the cheapest options nearby were at San Francisco International Airport, which is a short drive across the Bay Bridge from my home in Oakland.
But when I asked it to factor in the cost of an Uber or Lyft and to consider that traveling with a child meant that late arrival times were not ideal, the recommendation changed. Gemini determined that the airport in Oakland, which had earlier flights for a slightly higher price, was the best option.
Similarly, when I was looking for a hotel, sharing the details of my situation helped me get custom-tailored results. Taking into account that I was traveling with a toddler, Gemini recommended hotels in Waikiki that were family-friendly and easy to navigate with a stroller.
Now, I just need to make sure Gemini remembers to put a stroller on my packing list.
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