How to Use AI to Plan a Trip

I used to spend weeks building trip itineraries in spreadsheets. Tabs for every city, color-coded by day, nested rows for different options. I thought I was good at this. And then I planned my Portugal trip using AI and realized I had just been making it very hard on myself for years.

This is going to be a real walkthrough of how I actually did it, not a vague "just ask AI for recommendations" kind of post. Because vague doesn't help you.

Start with the conversation, not the itinerary

The biggest mistake people make is opening an AI chat and immediately asking for a day-by-day itinerary. Don't do that yet. You need to give the AI enough about you before it can give you anything useful back.

I spent maybe 20 minutes just having a conversation about the trip before I asked for any actual planning. I explained: two weeks, solo trip, I'd been to Lisbon before so didn't want to spend too much time there, I hate beach resorts and tourist traps but I love food and architecture, I'm pretty active but not a hardcore hiker, moderate budget, I wanted some slower days built in because I always over-schedule and exhaust myself.

That context completely changes what you get back. A generic "two weeks in Portugal" itinerary is going to send you to all the same places everyone goes. An itinerary built around my specific context was genuinely different, it suggested the Alentejo region which I'd never heard of, steered me away from the Algarve beaches I didn't want anyway, and built in actual rest days without me having to fight for them.

How to ask for recommendations you'll actually trust

Okay so here's the thing about AI and travel recommendations. They can be hit or miss on very specific stuff. If you ask "what's the best restaurant in Porto" you'll get suggestions that might be slightly outdated or just famous rather than actually great. AI doesn't have real-time information and it doesn't have taste.

What I do is use AI to build the framework and use it to give me the questions I should be asking, then verify specific things elsewhere. So I'd ask Claude things like: "For someone who wants to eat really well in Porto on a moderate budget, what neighborhoods should I be looking in and what type of places should I be looking for?" That gives me useful intel, like that the touristy spots near the Dom Luís bridge are overpriced and I should be looking toward Bonfim or Cedofeita for more local spots. Then I'd search for actual restaurants in those neighborhoods myself.

That combination works really well. AI for the strategic layer, your own research for the specific choices.

Building the actual day-by-day plan

Once I'd had enough back-and-forth to feel like the AI understood what I was going for, I asked for a draft itinerary. Not a final one, a draft. I made that explicit: "Give me a draft itinerary I can react to and edit."

What came back was something I could actually work with. Roughly organized by region so I wasn't backtracking constantly. Rest afternoons baked in after heavy travel days. A day in Évora that I wouldn't have thought to include and ended up being one of my favorites of the whole trip.

I'd go through it and push back on things. "I don't want to spend three days in Lisbon, can we cut it to one and a half and add more time in the Douro Valley?" "Is there anywhere between Porto and Lisbon worth stopping, or is that drive boring?" Those kinds of follow-up questions get really useful answers and you end up feeling like you've actually stress-tested the plan.

The logistics layer

This is where AI saved me the most time honestly. The logistics of a trip, how to get between places, whether to rent a car or take trains, how long drives actually take versus what Google Maps says when you factor in that you're going to stop and eat lunch, is incredibly tedious to research manually.

I just asked. "If I'm going from Porto to the Douro Valley and then to Évora and then to Lisbon, what's the best way to handle transportation? Do I need a car? Are trains reasonable?" And it gave me a genuinely helpful breakdown, that having a car was worth it for the Douro Valley and Alentejo because public transit is limited there, but that parking in Lisbon is a nightmare and I should drop the car before arriving.

I verified this with a few Reddit posts and it checked out. The AI was right and saved me probably two hours of research.

Packing lists are underrated

I know this sounds small but I got Claude to generate a packing list based on my specific trip and it was so much better than any generic packing list I've found online. I told it the time of year, the types of activities I had planned (city walking, some hiking, nice dinners), that I was doing carry-on only, and that I run warm.

It gave me a list that actually accounted for those things. Didn't suggest a heavy rain jacket because late September in Portugal doesn't really need one. Did suggest a light layer for evenings because the south can get cold at night even when days are warm. Reminded me that cobblestone streets are brutal and not to skimp on shoes.

My previous trips I've always either overpacked or forgotten something obvious. This trip I felt like I packed exactly right. I realize that's a small thing but after a decade of over-stuffed suitcases it genuinely felt like a win.

What AI still can't do

It can't tell you what a place feels like. I could ask Claude to describe Sintra and it would give me accurate information but it couldn't tell me that it gets genuinely overwhelming with tour groups by 10am and if you want to actually enjoy it you need to be there by 8:30. I learned that from a travel blog written by someone who'd been there recently.

It also can't account for things that change fast, restaurant closures, new places that opened last month, a festival that happens to be on the same weekend you're visiting. For anything time-sensitive I still cross-check with current sources.

And honestly it can't replace the serendipity of just wandering. The best meal I had in Portugal I found by walking past a place that smelled incredible at 1pm and going in without researching it first. No AI told me to do that. I'm just saying don't over-plan to the point where there's no room for that.

How I actually use it in the moment

I kept the conversation open on my phone the whole trip. Couldn't figure out where to eat in a specific neighborhood? I'd ask. Wanted to know the history of a building I was standing in front of? I'd ask. Found myself with an unexpected free half-day and needed ideas? Incredibly useful for that.

It's like having a travel companion who did a lot of research before the trip but is also fine with winging it in the moment. That's kind of the ideal combination.

I came home from Portugal feeling like it was the best-planned trip I've ever taken. Not over-scheduled, not stressed, not scrambling. The AI did a lot of the prep work that used to take me weeks and it did it in a few hours of conversation. I'm not going back to spreadsheets.