AI-Powered Itineraries Are Here—Should You Trust Them?

Planning a trip used to mean flipping through guidebooks or spending hours lost in travel blogs. Now? You can ask an AI to build your whole itinerary in under 60 seconds.

Just type: “3-day itinerary for Barcelona with food recommendations,” and boom—you’ve got a neat, hyper-efficient list of must-sees, where to eat, how to get there, and what to avoid. It feels like magic. But is it actually any good?

Let’s talk about it.

AI travel planning tools like ChatGPT, GuideGeek, or apps like Roam Around are exploding in popularity. They’re fast. Free. Available at 2am. And for the average traveler, they remove a lot of the mental load. No more 37 tabs open, no more second-guessing what’s “worth it.”

But while AI can give you the what, it still struggles with the why.

Sure, it’ll recommend the Louvre in Paris, La Sagrada Família in Barcelona, or the Colosseum in Rome. But those are the same things listed in every blog and TripAdvisor top 10. If you're looking for depth, personality, or hidden gems—AI isn’t quite there yet. It’s drawing from the internet, not from lived experience.

Then there’s the human touch. Ask a good travel agent where to eat in Kyoto and they might send you to a quiet family-run ramen shop down an alley with no sign—but unforgettable noodles. Ask AI? You’ll get the top-rated Google Maps option.

To be fair, AI is incredible for logistics. Want to organize train times between Italian cities or get a suggested packing list for rainy season in Costa Rica? It nails that. It’s fast, consistent, and doesn’t get tired of your endless “what if I land late?” questions.

But if your trip is more than just getting from A to B, if you want stories instead of lists, nuance instead of summaries—AI still can’t replace that. Not yet.

Here’s the sweet spot: use AI as your planning assistant, not your travel guru. Let it help organize your ideas, smooth your timeline, and answer all the “how” questions. But for the “what’s special?” and “what’s worth me seeing?”—talk to people. Locals. Travelers. Experts. Or just follow your gut.

Because at the end of the day, travel isn’t just about where you go—it’s about how you feel while you’re there. And no algorithm can feel that for you.

Yet.