This is how to use AI to plan a vacation better than Google can
Google gives everyone the same top ten list. Here’s how to get an itinerary built around how you actually travel.
This is how to use AI to plan a vacation better than Google can.
Search “3 days in Lisbon” and you get the same ten results everyone else gets, which is why everyone else is standing in the same line at the same viewpoint at the same hour you are. Google knows what’s popular. It has no idea what you’re like.
The move
Tell the AI who’s going, honestly. Not the aspirational version of you who wakes at 6am for sunrise hikes; the real version who wants one unhurried coffee before anything happens.
Copy this prompt:
Plan 3 days in Lisbon for two adults, mid-October.
How we actually travel:
- Slow mornings; nothing scheduled before 10am
- One “main thing” per day, not a checklist
- We care about food but hate waiting in lines
- Prefer neighborhoods over monuments; we like just walking
- Budget around $150 a day for the two of us, excluding hotel
- One of us has a bad knee, so flag anything with serious hills or stairs
Build each day with a morning, afternoon, and evening. Group things by neighborhood so we’re not zigzagging. For restaurants, suggest where locals actually go, and tell me which famous spots are skippable and what to do instead.
Why this beats the listicle
- It routes. Days grouped by neighborhood instead of crisscrossing the city chasing ranked attractions.
- It respects constraints. The bad knee isn’t a footnote; in a city built on hills, it reshapes the entire plan. No list article does that.
- It talks back. “Day 2 afternoon looks packed, thin it out.” “Swap the museum for something outdoors.” Try sending feedback to a blog post from 2023.
The two-check rule
AI itineraries have one classic failure: confident details that have quietly changed. Opening hours, closed restaurants, moved markets. So before booking anything around a specific place, verify two things: that it still exists and when it’s actually open. Thirty seconds per pin. The itinerary logic stays brilliant; the facts need a freshness check.
And once you’re there, the same chat becomes your pocket guide: “we’re near [square], it’s raining, lunch ideas?” That’s when it stops feeling like a tool and starts feeling like a friend who’s been there.
This is how to use AI.