I planned a 2-week Japan trip entirely with AI — including a custom day-by-day itinerary

Japan had been on my list for 10 years. When I finally booked the flights, I had no idea where to start with planning — 14 days, two of us, Tokyo to Kyoto and beyond. I spent about 3 hours with Claude and came out with the most detailed travel itinerary I've ever had for any trip. **How I approached it:** First, I gave Claude our full context: travel dates, budget, interests (food, temples, not too many museums), fitness level (happy to walk 15-20k steps), and one firm requirement — we wanted to see Mt. Fuji. Then I asked it to draft a rough outline: which cities, how many nights each, and logical routing to avoid backtracking. It explained the JR Pass and helped me calculate whether it was worth buying (it was). Then we went city by city. For Tokyo, I told it our neighbourhood (Shinjuku) and asked for a day-by-day plan that grouped nearby attractions together. It even suggested what time to arrive at popular spots to beat crowds. **The food research:** I asked it to recommend specific restaurants in each city for different meal types — ramen, sushi, izakaya, conveyor belt — with the caveat that I'd verify on Google Maps before going. It gave me a shortlist I then cross-referenced with recent reviews. **The outcome:** We followed the itinerary about 80%. The other 20% we changed on the ground based on mood — which is exactly right. The AI gave us a framework, not a prison. Best trip of my life. Sakura season. 10/10.

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