Can ChatGPT Plan Your Next Vacation? – AFAR Media

What are the Washington, D.C. sites that ChatGPT would advise a newcomer to visit?
Photo by Jacob Creswick/Unsplash
Whether you’re ready to embrace the future of AI or find yourself rewatching The Terminator with a familiar sense of foreboding, the rapid rise of ChatGPT can’t be ignored. The popular platform—which is owned by San Francisco-based research lab OpenAI and allows users to converse with a text-based, AI-powered chatbot—garnered more than 100 million active users in its first three months following its launch in late 2022 and has since earned its fair share of controversy. (The number of users also fell for the first time in June 2023, indicating that the initial fervor has died down.)
ChatGPT’s explosion nevertheless has forced society to confront difficult questions about whether artificial intelligence can, or should, stand in the place of human intelligence. Still, companies across industries have been quick to adopt the burgeoning technology, including in the travel and hospitality space, where heavy hitters like Bing, Expedia, and Matador Network have already begun integrating AI into a series of travel planning tools.
As someone with a general interest in evolving tech, I feel both skeptical and open-minded about the future of artificial intelligence and what it can do for us. As a travel editor, I wondered whether ChatGPT was capable of simply creating a comprehensive travel itinerary, let alone staging an I, Robot–style world takeover.
So I decided to let ChatGPT plan a weekend trip to a destination I was relatively unfamiliar with—Washington, D.C.—to see if it was up to the task.
I planned to check into the Waldorf Astoria Washington D.C., which sits steps from major attractions like the National Mall, the U.S. Capitol, and the White House. (Despite being one of the most recognizable buildings in the United States, the White House was—spoiler alert—noticeably absent from my itinerary.) Otherwise, my trip and I were entirely at the mercy of the robot.
Here’s what I learned about using ChatGPT to plan a trip—and whether I’d use it as a travel tool again.
Personally, the discovery phase—that magical time spent searching for inspiration—is what gets me psyched for a trip. I adore researching a destination to death, browsing social media for recommendations, and scouring Google Maps for little treasures that might not appear in standard guides.
With ChatGPT involved, I felt that I missed out on the best part of the trip: preparing for it. Not only that, but I also felt disconnected from my itinerary. The sense of anticipation and ultimate payoff I usually get from visiting a new place was essentially absent with “someone” else at the helm, even if I didn’t follow the schedule to a T.
Thus, if you, like me, are the type who loves plotting out the trip as much as taking it, you may want to skip ChatGPT during the “discovery phase” of travel planning.
That’s not to say there’s no room whatsoever for the travel planning–obsessed among us. In fact, when used correctly, AI can make for a solid planning partner.
Imagine that you and ChatGPT are working together on a group project. One of you will be the “big picture” person, focusing on the high-level details: the major cities, attractions, and other points of interest to hit. The other will be the logistics person, managing nitty-gritty details like the day-to-day itinerary and routes. But each of you can hold only one job.
In D.C., ChatGPT was my big picture guy, providing ideas for major stops in a destination unfamiliar to me, while I was the details person, checking to see whether the itinerary flowed well and rearranging as needed.
But out of curiosity, I tried asking ChatGPT to create a logical route for an upcoming trip to Iceland’s Westfjords, for which I had a few points of interest in mind but was struggling to map out the perfect route. In this case, ChatGPT was able to create a logical itinerary using my desired stops and did a great job of helping me get organized. In this example, I was the big-picture planner, and ChatGPT helped nail down the details.
Like any tool, learning how to use ChatGPT will take practice, and crafting a query that covers all of your bases may take you a couple of tries.
Your opinion of the tool’s usefulness will probably depend on your level of patience. For some, like yours truly, it may not be a big deal, and the novelty of the experience may even feel like a fun puzzle to solve. For others, it may get tedious—especially since you’ll not only need to spend time learning the tool but also fact-checking it and adjusting your schedule accordingly, too. (More on that later.)
As a best practice, the more specific you get with your ask, the better ChatGPT will become at tailoring an itinerary to your needs. At the very least, you’ll want to provide details like your travel dates, your interests, where you’ll be staying (unless you’re having ChatGPT help you decide this as well), your budget, how many are in your group, and whether it’s your first time visiting the destination. Don’t be afraid to use bullet points to avoid getting too wordy.
For example, here was the final query for my D.C. trip:
Hey ChatGPT! My boyfriend and I are traveling to Washington, D.C. from July 6– July 8. With the below information, could you create a two-day travel itinerary for us, including restaurants, bars, and attractions we should see while we’re in town?

One area where ChatGPT really struggles is timing—providing the accurate and adequate time that it takes to realistically get from one attraction to the next.
Photo by Chris Grafton/Unsplash

Perhaps the biggest argument against using ChatGPT as a travel planning tool is that its information isn’t always accurate. The platform’s newest model, ChatGPT-4—priced at $20/month—was most recently updated in March 2023, while its unpaid model hasn’t been updated since September 2021. This means that while an itinerary might sound good on paper, it may include businesses or attractions that are closed, for instance, or hours and entrance fees that are out of date.
Also worth noting, ChatGPT isn’t great at taking travel times into consideration or at creating an ergonomic schedule unless you specifically ask. On this trip, I found myself bouncing between neighborhoods rather than hitting attractions in a logical order. While 20–30 minutes on the train here and there doesn’t seem like a lot, it can quickly add up, not only disrupting the timing of your itinerary but potentially burning you out.
Although ChatGPT can pull decent recommendations, it’s up to you to do your due diligence and double-check opening hours, ticket availability, reservations, and whether factors like local holidays or temporary closures will affect your travel plans. (I learned this the hard way when I arrived, in D.C.’s sweltering midsummer heat, at the African American Civil War Museum and found that the indoor exhibition had been closed for renovations since March.)
At the end of each generated itinerary, ChatGPT mentions that all itineraries should be fact-checked. But if you miss the warning or, frankly, decide to hope for the best and put your trust in the bots, you may find yourself with an itinerary that promises more than it can deliver.
One thing ChatGPT can almost guarantee is that you won’t miss out on the essentials. With the exception of the White House, my itinerary covered the major attractions any first-time visitor to the nation’s capital would want to see, including the Smithsonian Institute, the National Mall, the African American Civil War Memorial, the Library of Congress, and the Capitol Building. Major tourist attractions aside, D.C. institutions like Ben’s Chili Bowl and 9:30 Club, an iconic, decades-old music venue, also made the list.
Although none of these suggestions came as a surprise, I did feel as though I was making the most of my relatively limited time in the city. If your goal is to see the highlights reel, ChatGPT will prioritize getting you there.
Essential stops aside, the bars and restaurants that ChatGPT offered up were good, but not amazing. I certainly didn’t come away convinced that AI can beat (or even match) recommendations from another human being, whether by word of mouth, a travel site, or a “Best things to do in ____?” thread on Reddit.
Chatting with one friend who visits the capital several times a year, she expressed that ChatGPT’s list was pretty good “for people who are only going to go to D.C. once and aren’t looking for any niche experiences,” and provided a few suggestions I felt more excited about from the jump.
Another friend, who currently lives in D.C., mentioned that the itinerary seemed too packed to be enjoyable and that the order of the itinerary “was not ideal in terms of economical travel,” two of my own major takeaways.
Overall, the likelihood of coming across new openings, local favorites, or hidden gems seems far less when you ask a robot for suggestions rather than a person—especially a person you trust to provide you with solid recommendations.
At the risk of stating the obvious, ChatGPT is not a human, and so it cannot account for the “human element”—those little things that can lead travel plans astray. It can’t predict how exhausted you’ll be after schlepping from attraction to attraction, or the crowds, or the sudden onslaught of summer heat or rain that renders an itinerary full of outdoor activities effectively useless. Even if you’re initially satisfied with your itinerary, be prepared to have a backup plan in place in case ChatGPT’s plan goes awry.
As AI travel tools evolve, I’ll certainly follow along and test out future tech. But for now, would I use ChatGPT to plan a trip again? Probably not. Lukewarm recommendations and “human elements” aside, I found that I spent just as much time crafting a query, fact-checking, and rearranging my schedule as I would had I developed an itinerary entirely by myself from the get-go—all without any of the fun one generally gets from travel planning on their own.

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