Planning trips can seem like a chore, a chore that AI chatbots should speed up. The technology was bad just a few years ago. Is it on task yet?
As a personal tech columnist for The New York Times and a frequent traveler, I was eager to see if AI could streamline the planning process that usually takes me hours of reading travel guides and plugging information into notepads and spreadsheets.
Last month I was mapping out the details of a 14-day trip to Taiwan and Hong Kong with my wife and our 20-month-old daughter, and I also wanted to help plan an upcoming summer vacation in Hawaii.
I had a lot of options, including sub-apps that use AI to book flights, as well as popular chatbots like ChatGPT and Claude. Since I find it’s usually easier to stick with one app than switch between multiple apps, I decided to focus on one.
I chose Google’s Gemini chatbot app for two reasons. First, unlike other chatbots, Gemini was already plugged into Google’s extensive resources for finding flights and places to eat, and second, I wanted to test it Ask for Mapsa new artificial intelligence feature built into the Google Maps app.
The good news: Chatbot Gemini, which was recently improved to provide more tailored answers based on personal data, and Ask Maps were a powerful combination that saved me time, especially when researching restaurants and tourist attractions. I only spent about 30 minutes planning my activities in Taiwan and Hong Kong.
The bad news: The twins occasionally made mistakes—like forgetting to include underwear on my packing list—so I had to do manual labor. Despite the imperfections, I generally recommend using Gemini as a virtual travel agent to help you plan your next trip.
Here is what I learned.
Chatbot with connection
Gemini is better equipped for trip planning than other AI chatbots because it has direct access to them Google Flights and Google Hotels for finding flights and accommodation. I’m also a firm believer that the joy of light packing also applies to travel applications, and the Gemini is essentially a Swiss army knife.
Google also recently released two new AI features that are useful for trip planning: Personalized intelligencean option that users can enable in the Gemini app settings, and the Ask for Maps button that recently started appearing in the Google Maps app.
Using personalized intelligence, Gemini can pull data from various Google services, including Gmail, Calendar, and your search history, and come up with its answers. In other words, if you ask Gemini, “Recommend me some restaurants near the hotel when I arrive,” he knows where you’re staying and the approximate time you’ll get there based on the information found in your email. I liked how quickly and efficiently I could get help from a Gemini without having to remind him of the details of my trip.
If you, like me, are interested in giving Gemini access to so much personal data, create a Gmail account that you use exclusively for travel and enable personalized intelligence only on that account.
In Google Maps, the Ask Maps button lets you ask conversational questions like “Can you explain Tokyo’s train facilities?” or “Is there a stroller-friendly route to the space museum?” and get Gemini-based answers 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 packages 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 created a handy line that included diapers, medicine, noise-cancelling headphones, and a power adapter. However, the bot neglected to add socks and underwear to the list for me, a 41-year-old who has never experimented with nudism. I added these two items manually.
I also asked Gemini to generate a list of important tasks to complete before the trip, and it came up with a useful summary that included checking the validity of family passports and researching cell service options abroad, another task I gave the chatbot. He recommended a cheap data plan that worked in both Taiwan and Hong Kong – perfect.
When I was satisfied with the lists, I asked Gemini to copy them into a notebook for later use. Lists appeared inside Leta Google notes app, with boxes to tick when I’ve completed tasks.
A talent for planning
Gemini shined at sketching out rough itineraries without me having to do much. I asked him to generate a daily activity plan, and since the Geminis already had access to my email flight and hotel reservations, and because they knew I was traveling with a toddler, they came up with an outline of activities for the family for each day. I asked Gemini to save the itinerary as a note in Keep.
We had a great time following the Taiwan and Hong Kong itinerary with my family – it even featured jet lag and short breaks with the toddler. For example, Gemini recommended to relax on foot on the first day in Taiwan Daan Forest Park and Yong Kang Street, an area nearby known for its restaurants. We enjoyed the walk and shared a bowl of delicious mango ice cream before returning to the hotel.
Mixed success in real time
While Gemini excelled at exploring ideas beforehand, it started to stumble when I needed help in real time. For example, when I arrived in Hong Kong, I asked it to recommend restaurants near my hotel, but it showed me a restaurant near my previous hotel in Taiwan. Google has said that personalized intelligence is still not complete and that timeline mixing is a known issue that it is working to improve.
Fortunately, Ask Maps handles these types of requests with gusto. One rainy day in Hong Kong, I opened Google Maps, tapped the “Ask Maps” button, and typed, “It’s raining. Find things to do with a toddler nearby.” The app suggested a visit to a science museum and gave me directions to get there in 10 minutes. My daughter, who is not easy to entertain, squealed with delight at the robotic dinosaurs.
Similarly, when I was standing on a street in a busy shopping district, I wrote, “Narrow down the restaurants on this street with good reviews.” Ask Maps immediately showed me several top-rated restaurants, including a shop that specialized in fried pork buns.
I brought them back to our hotel and the buns got rave reviews, including from an impatient 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 tour booking sites the old fashioned way. That’s because Gemini went beyond just prioritizing prices and rounded up the best options based on my personal situation.
For example, for my upcoming trip to Hawaii, I asked Gemini to find the best flight deals in July. The twins pulled information from Google Flights to show that the cheapest nearby options were at San Francisco International Airport, which is a short drive across the Bay Bridge from my home in Oakland.
But when I asked her to factor in the cost of Uber or Lyft and take into account that traveling with a baby meant late arrival times weren’t ideal, the recommendation changed. The twins decided that the best option was the Oakland airport, which had earlier flights at a slightly higher price.
Similarly, when I was looking for a hotel, sharing details about my situation helped me get tailored results. Since I was traveling with a toddler, Gemini recommended hotels in Waikiki that were family friendly and easy to get around with a stroller.
Now I just need to make sure Gemini doesn’t forget to put the stroller on my packing list.
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