I Let AI Plan My Two-Week Vacation — The Results Were Equal Parts Genius and Disaster
I'll be upfront: I went into this experiment as a skeptic. I've been planning my own trips for years — cross-referencing travel blogs, reading Reddit threads at midnight, building color-coded spreadsheets that my friends find both impressive and deeply concerning. So when everyone started raving about using ChatGPT to plan vacations, I figured I'd put it to a real test.
The trip: two weeks across Portugal and Spain, starting in Lisbon and ending in Barcelona. Budget: moderate. Travel style: a mix of culture, food, and some hiking. I used ChatGPT (GPT-4), Google's Gemini, and a dedicated AI travel tool called Layla for different parts of the planning process. I took detailed notes the whole time and then compared everything against what I actually encountered on the ground.
Spoiler: it was a genuinely mixed bag.
What AI Got Impressively Right
Building the initial framework was shockingly fast. I typed in my parameters — two weeks, Lisbon to Barcelona, moderate budget, interested in food and hiking — and within about 30 seconds, ChatGPT had produced a day-by-day itinerary that was, honestly, pretty solid. It suggested a logical geographic flow (Lisbon → Sintra → Porto → Douro Valley → San Sebastián → Bilbao → Madrid → Barcelona), correctly identified that I should spend more days in cities I'd listed as priorities, and flagged that I'd need to book the Alhambra tickets in Granada well in advance. That last piece of advice alone probably saved my trip.
The food recommendations were surprisingly specific and good. When I asked for restaurant suggestions in Porto, ChatGPT didn't just say "try the local seafood." It gave me neighborhood-level guidance, explained the difference between a tasca and a cervejaria, and suggested I eat a francesinha at a specific type of local spot rather than a tourist-facing restaurant. A lot of that held up when I got there.
It was great at answering logistical questions quickly. Things like: "What's the best way to get from Porto to San Sebastián?" or "Do I need a visa as a US citizen?" or "How far in advance should I book the Camino de Santiago accommodations?" — these kinds of questions got fast, accurate, well-organized answers that would have taken me 20 minutes of Googling to piece together.
Packing lists and practical prep were genuinely useful. I asked for a packing list optimized for a late-September trip across both countries, and it nailed it — right down to reminding me that Bilbao's weather can be dramatically cooler and wetter than Barcelona's, and that I'd want layers for the Douro Valley evenings.
Where Things Got Embarrassingly Off-Track
The AI had no idea what was actually open. This is the big one. ChatGPT confidently recommended a well-known wine bar in Lisbon's Bairro Alto neighborhood that, when I arrived, had closed permanently about eight months earlier. It also suggested a specific hiking trail near Sintra that turned out to be closed for restoration work. The AI presented both of these as current, reliable options with zero caveats. If I hadn't done a quick Google search before showing up, I would have been standing on a locked gate wondering what went wrong.
This is the fundamental problem: AI tools trained on data have a knowledge cutoff, and they don't always know what they don't know. Worse, they rarely say "you should double-check this" with enough urgency. They state things with the calm confidence of someone who has definitely been there, when in reality they've never been anywhere.
Crowd and timing estimates were way off. The AI told me that visiting the Jerónimos Monastery in Lisbon "early in the morning" would help me avoid crowds. I showed up at 9:15 a.m. on a Tuesday and walked into a full-on tour group traffic jam. The line for the Sagrada Família in Barcelona was described as "typically manageable" — it was a 90-minute wait despite having timed tickets. To be fair, I visited during a shoulder-season weekend, but the AI had no way of knowing that its baseline assumptions about crowd levels were built on pre-pandemic data mixed with post-pandemic travel surges.
Photo: Sagrada Família, via images.pexels.com
It completely underestimated travel times between cities. The AI's suggested itinerary had me doing a day trip from Madrid to Toledo AND visiting the Prado Museum in the same day. In theory, Toledo is only about 30 minutes by high-speed train. In practice, by the time you factor in getting to the station, waiting, exploring Toledo properly, getting back, and then spending any meaningful time at one of the world's greatest art museums — that's a 14-hour day minimum. I had to restructure that entire section of the trip on the fly.
Hotel and accommodation suggestions were hit or miss. One boutique guesthouse it recommended in Porto had reviews citing bedbugs as recently as three months prior. Another "highly recommended" option in the Douro Valley didn't take solo travelers. The AI pulled names from its training data without any real-time review aggregation, which meant I was getting suggestions that ranged from genuinely great to "please do more research before booking this."
The Lesson: AI is a Co-Pilot, Not a Captain
After two weeks of comparing AI recommendations to reality, here's where I've landed: these tools are genuinely transformative for the early stages of trip planning. The brainstorming, the framework-building, the logistical Q&A — AI compresses what used to take days of research into an hour of conversation. That's real value, and I won't pretend otherwise.
But the AI doesn't know what closed last spring. It doesn't know that a particular neighborhood has gotten rougher or that a beloved restaurant changed ownership and went downhill. It doesn't feel the difference between a 20-minute walk on a map and a 20-minute walk uphill in 90-degree heat with a backpack.
The smartest way to use these tools right now is to treat the output as a very well-read first draft. Let AI give you the skeleton — the route, the rough timing, the categories of things to do — and then verify every specific recommendation through current sources: recent TripAdvisor reviews, travel subreddits, the actual venue's website, and ideally a human who's been there in the last year.
The travelers who are going to get burned are the ones who screenshot the itinerary and book everything without a second look. The travelers who are going to thrive are the ones who use AI to cut their research time in half and then spend that saved time making smarter, more current decisions.
I'm already planning my next trip. And yes, I'm absolutely using ChatGPT to start. I'm just not letting it drive.
