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We’re taking this trip across four countries this July — five travelers, four hotels, three private drivers, a dozen trains, and more restaurant decisions than I want to count.
I love trip planning. I find it genuinely fun. But even I hit a wall somewhere around the third time I was cross-referencing train schedules against hotel checkout times against driver pickup logistics. At that point I did something I hadn’t done before: I handed the whole thing to Claude and asked it to build me a document.
What came back genuinely surprised me. Not because it was magic, but because it was actually useful — and the places where it wasn’t useful taught me something about what AI is and isn’t good at in travel planning.
Here’s the honest breakdown.
What I Asked It to Do
I had already done the foundational research myself. I knew the destinations, I’d booked the hotels, I had confirmed flights and private drivers. What I didn’t have was a way to hold all of it together in one place that multiple people could actually use — not just a spreadsheet, but something that could live on a phone, work offline, and be printed and tabbed for travelers who prefer paper.
So I gave Claude a detailed brief of everything I’d already decided and booked, and asked it to build a structured travel guide document. The prompt I used is at the bottom of this post — you can copy and use it directly.
What It Actually Built
The output was a comprehensive Word document with:
A day-by-day itinerary for every day, each formatted the same way: a daily overview, an hour-by-hour schedule, a self-guided walking tour with numbered stops and addresses, a dining section broken down by meal, a reservations summary, placeholder boxes for QR codes and screenshots, and a “Good to Know” section covering photo spots, coffee stops, restroom locations, and rainy-day backups.
City maps pages with placeholder spaces for printed maps plus clickable Google Maps links for every attraction and restaurant mentioned in the guide.
A restaurant section organized by city and budget ($ to $$$) with specific recommendations and brief descriptions.
A local foods guide for each country — what to order, what it is, where to find it.
Five packing checklists: carry-on, checked bag, hotel checkout, international travel, and flight home.
Budget trackers for daily spending, shared group expenses, cash, and credit card use.
Emergency information for all four countries — emergency numbers, hospitals, and US embassy contacts.
A master reservations log where all confirmation numbers could be filled in as they arrived.
What It Got Right
The structure was genuinely excellent. The idea of having every single day follow the same format — same sections, same order — is something I wouldn’t have done left to my own devices. I would have made some days more detailed and some less, depending on how much I knew about each place. Having the same bones every day means anyone can flip to any day and immediately know where to look for what they need.
The walking tours were solid starting points. For cities I know less well, it gave me a logical route through the highlights with enough context to evaluate whether the order made sense. I adjusted some sequencing based on what I knew about the actual geography, but I didn’t have to start from scratch.
The emergency information was something I would have put together eventually but almost certainly would have left incomplete. Having hospital names and embassy phone numbers for all four countries in one place, already formatted, was genuinely useful.
The packing checklists were thorough without being ridiculous. The hotel checkout list in particular — chargers, the safe, under the bed — is the kind of thing that lives in your head until you’re in a cab to the airport wondering if you left something plugged in.
What I Still Had to Do Myself
Almost all of the actual research.
The AI doesn’t know which restaurants are worth it right now. It can give you well-known names from its training data, but it can’t tell you which spots have declined, which are tourist traps that used to be good, or which new places have opened in the last year. For dining specifically, I still looked everything up on Google Maps and recent reviews before including anything.
It also can’t book things. The private drivers, the brewery tour, the walking and tasting tour — all of that required finding vendors, emailing or calling, negotiating prices, and confirming details. AI built the slots in the document where that information would go. The actual information required me.
The judgment calls about pacing were mine. The AI gave me an itinerary that looked complete on paper but needed real editing — accounting for different mobility levels in the group, that some travelers are not morning people, that Switzerland is genuinely expensive and we should build in more buffer time there. Those adjustments required knowing the people I was traveling with.
The local tips — the things that make a guide feel like it was written by someone who’s actually been somewhere — came from my own research, reading other trip reports, and asking people who’d made the same route.
When This Approach Works Best
It works best when you’ve already done your research and made your decisions, and you need help organizing it all into something usable.
It’s less useful at the research stage, where the quality of information matters more than the format. Start with the research yourself. Then use AI to help you build the container.
The Prompt You Can Use
Copy and paste this into Claude (or ChatGPT), fill in your details, and give it your confirmed bookings at the end. The more specific you are, the better the output.
I'm planning a trip to [Destination 1], [Destination 2], [Destination 3], and [Destination 4]
from [Start Date] to [End Date] with [Number of Travelers] travelers,
flying from [Home Airport].
Please create a comprehensive printable travel guide for me in a clean,
structured format. The guide should work both printed and on a phone.
Include these sections:
COVER PAGE with destinations, dates, travelers, and flight route.
TRIP AT A GLANCE with a route table (nights, city, hotel, country),
flights summary, and a placeholder map box.
HOTELS — one entry per hotel with address, phone, check-in/out dates,
confirmation number blank, room notes, and Wi-Fi placeholder.
TOURS & TRANSFERS — detailed entry for each booked tour or private driver,
including pickup/drop-off, route, stops, payment, and driver name blank.
DAILY ITINERARY — one section per day, each with:
- Daily overview paragraph
- Weather and transport line
- Hour-by-hour schedule table
- Self-guided walking tour with numbered stops (name, Google Maps link, description)
- Dining by meal (coffee, lunch, treat, drinks, dinner)
- Local foods to try that day
- Reservations table for that day
- QR/ticket placeholder boxes
- Good to Know (photo spots, coffee stops, restrooms, rainy-day backup,
packing reminder for tomorrow)
- Notes lines
CITY MAPS — one per city with placeholder map box, hotel/station links,
bulleted attractions and restaurants.
QR CODE VAULT — placeholder boxes for hotels, transport, tours, restaurants.
RESTAURANT RECOMMENDATIONS — by city and budget ($ / $$ / $$$).
LOCAL FOODS TO TRY — by country/region, with dish names and descriptions.
TRANSPORTATION — airport transfers, train routes, tips, private driver table.
PACKING CHECKLISTS — carry-on, checked bag, hotel checkout,
international travel, flight home.
BUDGET TRACKERS — daily spending, shared expenses, cash log, credit card log.
EMERGENCY INFORMATION — emergency numbers, hospitals, embassy contacts,
money/power/customs summary.
RESERVATIONS & CONFIRMATIONS — master log tables for hotels, drivers,
tours/tickets, and trains.
NOTES — blank lines for journaling.
Here are my confirmed bookings:
Flights:
- [Outbound: Date, Airline, Flight #, Route, Departure time, Arrival time]
- [Return: Date, Airline, Flight #, Route, Departure time, Arrival time]
Hotels:
- [Hotel Name, City, Dates, Full address, Phone number]
- [Hotel Name, City, Dates, Full address, Phone number]
- (continue for each hotel)
Confirmed tours and transfers:
- [Date: What, time, price, payment method, any stops]
- [Date: What, time, price, payment method, any stops]
- (continue for each booking)
Any other confirmed items:
- [Description, date, details]
Please format every walking tour stop with a Google Maps link using:
https://www.google.com/maps/search/?api=1&query=%5Bencoded+place+name%5D
Make the structure identical for every day so it’s easy to navigate
both in print and on a phone.A few things to check before you use the output: verify all restaurant recommendations are current (AI training data gets stale), double-check train schedules and prices on the actual rail website, and fill in the blanks that only you can fill in — confirmation numbers, driver names, your actual preferences on pace and how much walking the group can handle.
The AI builds the container. You fill it with the real trip.
One More Thing: Document It While You’re There
The planning gets you to the trip. The journal brings it home with you.
Every travel journal I picked up over the years assumed I wanted to schedule my days down to the minute and tick off a list of sights. That’s never been how I travel. So I made one that isn’t like that. Cozy Travels is a comfort-first travel journal with a pace tracker on every page, a Comfort Find of the Day prompt, and room for the slow moments that don’t make it onto any itinerary. It’s the journal I wished I’d had on every trip I’ve taken.
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Practical Cozy Travel 