Planning a trip with ChatGPT? Pros and cons to the AI tool

When I started planning a summer trip to Greece, I decided to enlist an unusual assistant: ChatGPT.

The artificial intelligence tool promised a custom itinerary in seconds. On the surface, it was sleek, efficient and free. But could it really deliver?

Here’s what worked, what didn’t, and how travel agents say AI stacks up.

The promise: Instant itineraries

I gave ChatGPT my basic trip details and a prompt: "I will be taking a nine-day trip from New York to Greece in August with seven friends. I first want to fly to Mykonos for three days, then spend three days in Paros and two days in Santorini. Please build a custom itinerary including suggestions for flights and ferries, places to eat and get coffee, beach clubs and nightlife."

Within seconds, it spit back a polished schedule, complete with a map of the Greek islands and even a YouTube link to Mykonos beach clubs. It recommended specific restaurants, nightlife spots and ferry transfers.

Honestly, it was impressive. If you’re overwhelmed by the sheer amount of travel content online, having a clear day-by-day framework in under a minute feels like magic.

The pitfalls: Details matter

However, once I dug into the recommendations, reality did not always match.

The connecting flights ChatGPT suggested cost $430, which seemed staggeringly low. The link it provided revealed a 15-hour layover, turning it into a 24-hour trip. With a quick Google search, I found a more realistic option: a round-trip American Airlines overnight flight from Kennedy  to Athens for $1,100 and a $160 Aegean Airlines connection to Mykonos. More expensive, but faster, practical and realistic.

Some restaurant picks had closed permanently, lingering only on old blogs and Reddit threads. One Santorini suggestion, Metaxi Mas, did not accept reservations and was difficult to reach without a car. My friends and I instead stumbled upon Mama Thira Tavern, a spot with ample seating and Caldera views. The food was so good we went back the next day.

That is the risk. ChatGPT can get you 70% there, but the final 30%, the practical details, can make or break a trip.

What travel agents say

"It is a rough draft, but not the final copy," said Gaylynn Innes, a Massapequa-based adviser with Magical Moments Vacations. "AI can give you a rough outline, like Google, but it does not replace the experience of someone who has actually been there."

Innes said she spends much of her time in training and site visits: checking whether Cancun beaches have seaweed, testing restaurants, or learning which Universal Orlando rides to prioritize to avoid wasting precious park hours. Beyond logistics, she said agents have the connections to step in if something goes wrong.

"It is like the difference between fast food and a Michelin-star restaurant," she said. "You can get something quick, but the experience is not the same."

Christine Earls, owner of You and Me By The Sea Travel in Islip, recalled a client who handed her a ChatGPT-generated Amalfi Coast itinerary.

"It included airfare for $400," she said. "On paper it looked great, but the flights were not realistic, with multiple stops and seasonal pricing ignored. AI does not give accurate quotes."

Earls said she sees AI as a research tool, not a booking tool. "It is like doing a science project without guidance," she said. "With a human, you are not just a number. We know your seat preference, dietary needs, accessibility requirements. Sometimes we can even get perks like onboard credit. AI does not do that."

The takeaway

While I find planning fun, I was open to having a strong foundation laid out for me, something I could customize to my preferences. For my Greece trip, I blended both approaches: ChatGPT for a starting framework, my own research for updated flights and ferries, and word-of-mouth recommendations to fill in the gaps. Some of the best restaurants and beaches I visited were either stumbled upon or suggested by locals. The result was a trip that felt personalized, something AI alone is not ready to deliver.