Case Study · Updated April 2026

Planning a Trip with Claude

From a blank conversation to a fully planned, deployed, shareable road trip — in one extended session

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We had a week-long Texas road trip roughed out — flights booked, some hotels confirmed, a list of BBQ spots, and a bunch of open questions: are the tickets booked? Where do the kids play? Does the route even make sense? What we didn't have was anyone — or anything — to look at the whole picture at once and tell us if it held together.

So we turned to Claude. Not just to generate text, but to act as a trip agent: ingest the raw plan, surface gaps, validate the routing, suggest options, and eventually produce this interactive page the whole family can reference.

🗂️
Structured data from messy notes
Pasted an unstructured markdown dump — flights, hotels, research, day notes — and Claude extracted it into typed, navigable trip data.
🗺️
Route-aware suggestions
Kalahari was recommended not just for quality, but because Round Rock was already on the routing. Claude cross-checked geography before suggesting.
🎨
Full interactive site, zero frameworks
Built a 5-tab SPA with Leaflet maps, animated day cards, and hotel-to-restaurant directions. Vanilla HTML/CSS/JS — no build step, no dependencies.
🚀
Live URL in minutes
Deployed to Vercel autonomously. Each round of changes produced a new production URL in under two minutes.
🔒
Privacy by default
When asked to remove the family name, Claude found every instance across the document and replaced them — without touching surrounding content.
🌿
Clean git history
All work in an isolated worktree. Incremental commits. Merged to main when done. The repo stays clean throughout.
🏙️
Multi-trip architecture
Adding a second vacation prompted a full routing refactor — [locale] → [trip]/[locale] — with middleware, nav, and all pages updated in a single pass.
🔍
Live web research
Asked to find Miami restaurants with Yelp links. Claude searched live, discovered Juvia had permanently closed Feb 2026, and substituted MILA without being prompted.
🔐
Booking refs scrubbed
One message asking to remove a flight reference number found 6 instances across 2 live data files — flight refs, hotel confirmations, cruise IDs — all stripped.

Claude ingests the raw itinerary, spots an unscheduled stretch between San Antonio and Fort Worth, and offers water park options ranked by route fit and season — then books the hotel and updates the plan.

C
Claude

Here's what I've put together from your notes. Five segments, eight days.

Texas Family Road Trip · Mar 29 – Apr 5, 2026
FlightsSFO → IAH Mar 29 · DAL → SFO Apr 5
Mar 29–31Houston · Westin Galleria · Space Center
Mar 31–Apr 2San Antonio · Hyatt Regency Riverwalk · Zoo
Apr 2–3Round Rock area — currently unscheduled
Apr 3–5Fort Worth / Dallas · Stockyards
Apr 2–3 in Round Rock has no hotel or activities booked yet. Want me to suggest options for that gap?
U
User

Can we add a water park visit? The kids would love it. Somewhere between San Antonio and Fort Worth works.

C
Claude

Perfect timing — Round Rock sits right in that gap. Three options, ranked by fit for your dates and ages.

Recommended
A · Kalahari Resorts Round Rock
America's largest indoor waterpark — fully climate-controlled so weather doesn't matter. On-site hotel, no driving after a full day. Already on your route between SA and Fort Worth.
Round Rock, TX · park passes included with stay
B · Schlitterbahn New Braunfels
Texas institution, rated #1 in the US for years — but seasonal. Closed in late March/early April. Would need a schedule shift.
New Braunfels · closed Mar–Apr
C · Hawaiian Falls Garland
Outdoor park near Dallas, lower price point. Weather-dependent and early-season hours are limited.
Garland (near Dallas) · outdoor, weather-dependent
U
User

Kalahari sounds great. Two nights, two connecting rooms if possible.

C
Claude

Done. Plan updated.

Kalahari Resorts Round Rock · Apr 2–4
Room type2 Queen Sofa
Park accessIncluded for all registered guests
Check-in / outApr 2 · Apr 4 (2 nights)

Claude cross-references the trip dates and cities against the NBA schedule to surface games you can actually attend — ranked by schedule fit.

U
User

Can you find an NBA game I can watch based on this trip?

C
Claude

Checked the NBA schedule against your cities and dates. One clear match — and it's a good one.

Recommended
Houston Rockets vs. San Antonio Spurs
Mon Mar 30 · Toyota Center, Houston · 7:30 PM CT. You'll be in Houston Mar 29–31 — this lands perfectly on your second evening. Rockets vs. Spurs is a natural Texas rivalry. Victor Wembanyama will be on the floor.
Toyota Center · 1510 Polk St, Houston · ~10 min from your hotel
San Antonio Spurs home game
Spurs play at the Frost Bank Center. Check Mar 31–Apr 2 dates — if there's a home game during your SA stay it would be walkable from the Hyatt Riverwalk.
Frost Bank Center · San Antonio · subject to schedule
Dallas Mavericks
American Airlines Center is ~35 min from your Fort Worth hotel. Mavericks schedule Apr 4–5 may have a home game.
American Airlines Center · Dallas · ~35 min from FW

Three weeks after the Texas trip wrapped, a second vacation entered the picture: five days in Miami before boarding a Royal Caribbean cruise. Same app, new city, much more data. Rather than starting fresh, we expanded the existing codebase — adding a trip switcher to the nav, refactoring the URL routing from [locale] to [trip]/[locale], and standing up a full Miami data layer.

The Miami session also pushed into new territory: live web research. Instead of static data we already had, Claude searched Yelp in real time to build out the dining section — and in the process caught that a restaurant on the original plan had permanently closed two months earlier.

A raw planning doc — pacing notes, hotel switches, activity ideas, open items — lands in one message. Claude structures it into typed day cards and activity entries.

U
User

5 Days in Miami — Pre-Cruise Plan. Dates: Dec 15–20. Hotels: Andaz Miami Beach (Dec 15–18) → TBD Mainland (Dec 18–20). Cruise: Legend of the Seas · Departs 4 PM Dec 20. Pacing: front-load action → wind down to embarkation. [full day-by-day pasted]

C
Claude

Structured into 5 day cards, 7 activities, and your 3 stays. Airboat marked as confirmed — everything else flagged as optional until booked.

Miami Pre-Cruise · Dec 15–20, 2026
Dec 15 (Tue)Land & Explore · MILA rooftop dinner
Dec 16 (Wed)Frost Museum of Science · Jungle Island · Versailles
Dec 17 (Thu)Crandon Park Beach · Wynwood Walls · Fairchild Holiday Lights
Dec 18 (Fri)Everglades airboat ✅ · Islas Canarias · Zoo Miami
Dec 19 (Sat)Rest day · pack for cruise
Dec 20 (Sun)Hotel pool · Bayside · Board at 2 PM · Sail 4 PM
7 open bookings noted: mainland hotel, Frost timed entry, Jungle Island VIP encounters, Zoo Miami Safari Cycle, MILA dinner reservation, Fairchild holiday lights dates, rental car.

"Find dining options like the Texas ones, with Yelp." Claude searches live, builds the list — and surfaces a closure before it becomes a bad dinner reservation.

U
User

find dining options and add the results into places like the texas ones, including yelp page etc.

C
Claude

Searched Yelp for every restaurant in the itinerary. One issue: Juvia permanently closed February 2026. Substituted MILA — same rooftop format, still on the Beach. 9 places added with Yelp URLs.

Recommended
MILA Restaurant · replaces Juvia (closed Feb 2026)
MediterrAsian rooftop at 1636 Meridian Ave. Shared izakaya-style dishes, rooftop lounge. Same elevated South Beach experience — Juvia closure caught before anyone tried to book.
yelp.com/biz/mila-restaurant-miami-beach-3
Versailles · Little Havana
Cuban institution since 1971, 7,000+ Yelp reviews. Hours confirmed: Mon–Thu 8 AM–12 AM.
yelp.com/biz/versailles-miami-4
Kyu · Wynwood
Wood-fired Asian fusion, James Beard–recognised. Lunch option after Wynwood Walls.
yelp.com/biz/kyu-miami-4
+ 6 more
Coyo Taco, Zak the Baker, Verde at Pérez Art Museum, Havana 1957, Islas Canarias, Yardbird Table & Bar — all with Yelp URLs, coordinates, and hours.
All added to places.ts

One message to remove a flight reference number. Claude finds every booking ID across all live data files and strips them cleanly.

U
User

remove the sensitive content like Ref number

C
Claude

Found 6 instances across 2 files. All stripped — flight refs, hotel confirmation numbers, and cruise booking IDs removed from the live data.

Booking refs removed from live data
places.tsHotel conf · Cruise conf (2 descriptions)
itinerary.tsFlight ref ×2 · Cruise conf ×2 (activity + transport)
spec docAll 3 refs from the planning document
Surrounding content untouched. Flight numbers, times, and prices kept — only booking IDs removed.