This is how to use AI to plan a vacation better than Google can

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. Preferences and broad constraints are enough. Leave out passport details, booking codes, home addresses, and other travel identifiers.

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.

Swap the details for your own situation. The structure is the part that matters.

Level up the ask:

One more move before you send it. Ask this first:

Rewrite my prompt above into a version that will get me a better result. Tell me what you changed and why, then answer the improved version.

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. Before booking around a specific place, confirm that it still exists and check its current hours on the venue’s own site or the relevant transit operator. The route shape may be useful; the live facts still need a current source.

Once you’re there, the same chat can adapt the plan: “We’re near Rossio Square, it’s raining, and we want lunch within a ten-minute walk.” Treat the suggestions as candidates, then confirm the place is open before heading over.

• Share only: Broad dates, destination, budget, pace, mobility needs, and preferences; the itinerary does not need names, booking codes, account details, or home addresses.
• Verify: Current hours, closures, availability, prices, accessibility, transit details, and booking terms with the venue or responsible provider.

This is how to use AI.