14 days in Japan with Claude Code: Obsidian planning, a private offline trip app, and live re-planning
o_vieira · reddit · 2026-10-15
A Redditor's full writeup of using Claude Code as a travel assistant for a 14-day Japan trip (Kyoto → Hakone → Tokyo) with his wife:
1. Planning in Obsidian: Itinerary, bookings and research notes live in his vault. Key tactic: have Claude "grill" him — one question at a time with a recommended option — keeping decisions his own, plus a "run check" over each city's days for problems.
2. A private trip app: One encrypted HTML file on Vercel, offline-capable with an update button. Features evolved on the road: day cards with times/directions/hours, booking QR codes, per-city train guides (greatly detailed after getting lost early on), taxi cards with the hotel address in Japanese, shopping lists with tick boxes, and stories per stop. Passwords and tokens stayed in macOS Keychain, invisible to Claude.
3. Live mode: The desktop session ran at home with Remote Control on (plus a routine to restart it), so from his phone: "we missed the 10:15 train, re-time the day" — app and calendar updated in minutes.
4. What went wrong: A spur-of-the-moment stop wasn't verified and was closed; after that, every stop gets checked on its official website.
Tips: let the AI grill you, verify official sources and state what couldn't be verified, keep one source of truth, keep secrets out of the chat.
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