Planning a real trip with Claude (and live flight data)

We had two weeks off this summer and a genuinely awkward set of constraints for a trip. Only one of us drives, we had a health reason to stay near good hospitals and keep the travel gentle, we both have a longish list of foods we don't eat, and I wanted somewhere with a real view, a kitchen, and decent coffee. Planning it with Claude turned into one of the better examples I have of using AI for a real decision, so here's how it actually went. Messy parts included.

This took a lot of iterating. The trip went through three different destinations before it landed. We fully planned Scotland, then postponed it (too far from care, too much driving). We built out Madeira and Northern Spain as finalists and couldn't choose. We ended up on the northwest coast of Tenerife. The value came from the loop, and from Claude asking questions and challenging assumptions along the way.

The method

The shape is the same one I use for most decisions. I describe the thing and ask Claude to interview me before it proposes anything:

Come up with a plan to find these the best way possible. Also ask me questions to finetune what I want to find. Are there airbnb/booking mcp servers?

Then the trick I'd actually pass on: taste calibration. If someone asks "what kind of place do you want?", you get nowhere, because you can't describe your taste in the abstract. But you can recognize it. So instead of adjectives, I sent four specific places I already love, and Claude pulled out the traits they share (design-led, small, the view as the whole point, some kind of outdoor soak, dropped into a landscape). One listing gives you a property. Five give you a taste.

From there it's tight loops, and each pass adds exactly one hard constraint. You can watch the search narrow just from my prompts:

"only find places at max €500 per night, available a week in July or August"
"cap at €380 per night. Also include the vicinity of good [medical] care"
"focus on great views, elevated over the sea, ideally mountains behind it"
"I think 30–31° average is too much. Up to there is ok"

That fourth one is what split Tenerife into "the hot south, no" and "the cool cloudy north, yes." Each constraint got written into a doc I keep, so the reasoning didn't vanish into chat scrollback.

Photos lie, satellite doesn't

Here's the step that changed the outcome most. Listing photos are marketing, and marketing hides everything. A "sea view" can be a five-degree wedge between two apartment blocks. A "secluded" place can back onto a building site.

So before anything made the shortlist, Claude verified it: Google Maps satellite to see if the view actually exists and what's next door, Street View for power lines and half-built villas, and a scan of the reviews for whether people actually mention the view. Only then did it get scored. This needs a real browser (Airbnb blocks plain fetches), which Claude drives through the Playwright MCP.

The part I'd tell the r/ClaudeAI crowd

The best moment was the flights, because it's a clean example of AI plus live data on a real decision.

I had a slightly odd idea to make the travel day gentler: instead of one long haul, fly to a hub in the evening, sleep at an airport hotel, take a short morning flight onward. Here's how I put it:

We are even thinking about super creative options to make it as relaxing as possible (evening flight to a hub, airport hotel, morning flight onward). We want to fly business or free-middle-seat economy to make the trip as comfortable as possible.

Normally I'd guess whether that was affordable and probably not bother. Instead, Claude priced that exact shape against live Google Flights data (through SerpApi), including the multi-city routing:

HAM → LIS (evening)  +  LIS → TFS (next morning)
  cabins checked: economy, premium, business
  both island airports at once: TFN and TFS
  compared against the plain direct flight

It came out reasonable, so we booked it: an overnight in Lisbon on the way out, then a short hop the next morning. I came up with the idea, the AI validated it against real fares in minutes, and we booked the thing. There was a nice side-quest too, comparing airlines by whether my bike box actually fits their cargo rules, which no normal flight search lets you filter on.

Turning the decision into a tool

We still couldn't pick the final place. Rating listings out loud at the table doesn't work, because the louder opinion just wins. So I asked:

Ideally we can mark them good/bad each (think swipe left/right). Find an easy way for us to do that. I think a database would be overkill.

Claude built a tiny swipe-vote page. Each of us swipes through the shortlist on our own phone, and a share link reveals what we both liked, what only I liked, what only they liked. No backend, the votes just live in the browser. I hosted it on my own NAS so my partner could scroll through it on the couch. That's the moment "planning with AI" turned into a small tool a real couple used to decide.

The honest part

It worked. We reached a confident, specific choice we both felt good about, and booked flights that matched a genuinely useful idea. And plenty broke along the way. The compare feature on the swipe tool shipped broken the first time (a naming clash in the code). The self-hosted page rendered blank at first. Claude hit rate limits and fell over mid-task more than once. A rental car we booked later became unavailable.

My favorite honest detail: the planning outran its own paperwork. The tidy folder on my disk still says "deciding between Madeira and Northern Spain," because the real decision moved on and lived somewhere else. State drifts. If you don't keep one index as the source of truth, your own notes start lying to you.

At the end I had Claude take the whole workflow, strip out our personal details, and turn it into a reusable toolkit I pushed to GitHub. Which is very on-brand for this site: here's the messy real thing, and here's the cleaned-up thing you can use.

If you plan a trip with Claude, do the taste-from-examples step and the satellite check. Those two did more for the final result than any amount of describing what I wanted :)