How I Let AI Plan My Entire Trip—And What Actually Happened

I didn’t plan a single thing. Not the flights, not the restaurants, not even the outfit for day three. I handed the whole thing over to artificial intelligence—and hit “confirm.”

At first, it was a joke. I was exhausted, scrolling TikTok at midnight, and saw someone using AI to plan a solo trip to Portugal. The comments were half awe, half disaster stories. Something in me lit up. Could I really outsource travel planning and still have an amazing trip?

Spoiler: yes. But not in the way I expected

Step One: Giving Up Control (Kind Of)

I used a mix of tools: ChatGPT for the itinerary, Expedia’s AI assistant for bookings, and a new app called Roamie that builds real-time suggestions based on your travel style. I told it I liked street food, bookstores, ocean views, and getting slightly lost. I said I didn’t care about luxury, but I did want magic.

The result? A five-day plan for Lisbon and nearby coastal towns, sprinkled with sunset spots, pastel de nata shops, and an afternoon tile-painting class.

Was it perfect? No. Did I follow every step? Also no. But it gave me a frame—and the freedom to improvise without stress.

Why It Worked Better Than I Thought

There’s something weirdly calming about letting a machine handle the logistics. I didn’t waste hours comparing Airbnbs or second-guessing train schedules. I wasn’t overwhelmed by endless options. I just... showed up.

One day, Roamie suggested a detour to a lesser-known beach near Cascais. It wasn’t even on the tourist blogs. I arrived to find a sleepy cove, no crowds, and a tiny café with grilled sardines that tasted like summer. That was the moment I realized: AI can’t manufacture magic, but it can make space for it.

Where It Fell Short (Because Of Course It Did)

AI still doesn’t know how to read vibe. It told me a jazz club in Bairro Alto was “intimate and authentic,” but when I got there, it felt more like a stag party with saxophones. I left early and found a quiet wine bar around the corner with live Fado music and one older man playing guitar alone. That moment wasn’t on any itinerary. It felt stolen—and earned.

Another hiccup? Restaurant suggestions. AI loves places with lots of reviews, which doesn’t always mean they’re good. One dinner was painfully bland. But I learned to take the suggestions as starting points—not gospel.

The Unexpected Perks

You know how planning can sometimes feel like you’re working before the fun begins? This trip didn’t have that. I let the tools do their thing, then I edited in real time. It felt less like a rigid schedule and more like jazz. AI laid down the rhythm, and I riffed.

Also: no decision fatigue. That’s the sneaky killer of good trips. Where to eat? What to do? Should we Uber or walk? AI gave me default answers I could accept or reject. I had more mental space to actually enjoy being there.

Conversations Got More Interesting

Because I didn’t spend hours poring over travel blogs, I asked more people for recommendations. Locals, baristas, fellow travelers. And those conversations led me to spots I never would’ve found. AI gave me a path, but people made it come alive.

One guy I met at a lookout point in Alfama invited me to an open-air poetry reading in a courtyard lit with string lights. It wasn’t on the internet. It wasn’t optimized. It was unforgettable.

Would I Do It Again?

Absolutely. Not for every trip. But for the kind where you want adventure without overwhelm? It’s a game-changer. I think of AI as the assistant who’s great at logistics but doesn’t mind if you change your mind.

I still kept a small notebook, wrote every night, and wandered aimlessly when it felt right. The difference is that I never felt behind. I never felt like I was missing something—because the plan was already there. And I was free to rewrite it.

What I Learned About Travel (And Myself)

Letting go of total control didn’t mean having a worse experience. It meant having a different one. One with fewer tabs open and more eyes-up moments.

AI didn’t take away my adventure. It gave me more room to have one.

So if you’re planning a trip and feel stuck in research overload, maybe do the scary thing. Let the machine write the plan. Then go live the story yourself.

Because the best parts of travel still can’t be predicted. But they can be made possible—with a little help from your robot friend.