From Priceline’s new AI assistant, Penny, to fully planned itineraries from Google’s Gemini, artificial intelligence is tiptoeing into the world of travel.
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Tiptoeing might not be the right word now that tens of thousands of Americans are using (or are planning to use) AI to organize their trips in 2025.
Whether booking tours or digging deeper to research restaurants and museums, AI tools and assistants are taking a load off for tired travelers.
At least, in theory.
AI remains in its infancy, meaning many of its use cases still aren’t hammered out. On top of that, most suggestions are based on data-driven calculations—and data isn’t always as reliable as we like to think.
Plus, using an AI program to its full capacity takes a bit of practice. It’s not something a newcomer will land with a few quick questions.
To be clear, I’m not doubting the efficacy or usefulness of AI when it comes to trip planning, but I’d hate to paint an overly optimistic portrait. While you should be leaning on AI to offload some of the work, don’t fall into the mindset that you don’t need to do any double-checking.
Here’s what you need to avoid when using AI for trip-planning.
Common mistakes travelers make using AI to plan trips
Mistake #1: Not double-checking suggestions
For me, the best use for AI and trip planning is to point me in the right direction. In other words, I’ll collate a list of suggestions from leading AI assistants, from Priceline’s Penny to Google’s Gemini, and then rank them in order of my favorites.
From there, I go through the list to make sure that each suggestion (whether a destination, museum, or hotel) meets my needs. Remember that some models might be using outdated information. You always need to double-check.
Mistake #2: Staying too broad
In my experience, AI tends to paint with broad strokes when it comes to recommending activities, tours, hotels, restaurants, and more. Remember that some AI programs don’t ‘know’ you as a user, meaning they aren’t creating personalized suggestions for you.
You need to dig deeper to get more out of those suggestions. To do so, I recommend using adjectives that describe you and the type of travel experience you’re looking for. Avoid broad terms when possible.
*If you’ve been using a single AI model, then this might not be true. For example, if you regularly use Google Gemini, its suggestions might be more tailored based on your previous patterns.
Mistake #3: Using general AI tools—and only one
Using ChatGPT or Gemini isn’t the best way to utilize AI to plan trips—point blank.
The best AI tools for planning trips are those that were designed specifically to plan trips. I’m not just talking about Priceline’s Penny assistant, either (although she is cool).
Other tools have popped up in the last few years, from GuideGeek to MindTrip. I highly suggest using these types of travel-centric AI programs. Not only are they specific to travel, but they’re also prepared to help you do things like budget to the dollar, uncover hidden gems, and find a perfect lodging for your group.
On top of that, I suggest using a few different tools to see which generates the most satisfying trip. Given these programs aren’t going to actually book anything for you, this lets you put together a perfect trip based on advice from multiple AI tools.
Mistake #4: Accepting the first suggestions
If you’re new to planning trips using AI, then you might be tempted to see the first list of suggestions and start booking trips. In reality, you should continue tightening the itinerary by correcting elements you don’t like and asking for more suggestions.
Remember—AI is there to serve you while also learning from you (in most cases). The more you nudge and steer the results, the more tailored of an adventure you’ll have.
Mistake #5: Ignoring the plug-ins
AI comes in a few well-known forms, mostly chatbots (like ChatGPT) and predictive algorithms. Chatbots are the more dynamic option while algorithms work behind the scenes to curate options that travelers want to book, from tours to flights.
But there are also plug-ins. For example, you can install a ChatGPT plug-in that’s specific to travel in order to assist the AI model in finding the right results for you.
In the case of the Trip.com plug-in, you can even research trip details like flights, hotels, and more. Expedia also has one active, letting you more seamlessly plan a trip using the capabilities of OpenAI with the expertise of a travel platform.
