The problem
Planning a multi-day outdoor trip — say, three days of kayaking, biking, and hiking around Moab — means twenty browser tabs, conflicting schedules, and no way to know if any of it is actually available until you call. AI trip planners give you prose; they don’t give you reservations.
The insight
The hard part isn’t generating an itinerary — it’s grounding one in real availability and real bookings. That’s a data problem before it’s an AI problem, and it’s exactly the data TripOutside already has: curated experiences, live availability, real outfitters.
How it could work
- Start from constraints, not inspiration: dates, group, fitness, “we have one rest day.” The planner assembles from actually bookable inventory.
- Every leg of the itinerary is a hold that can become a reservation in one action.
- Weather or closure changes trigger replanning against live availability.
- Outfitters get multi-day, multi-activity customers they’d never reach alone.
Why me
This is the natural extension of TripOutside — the inventory, availability integrations, and outfitter relationships already exist. The planner is a new front door on a marketplace I already operate.
Open questions
- Standalone product or a TripOutside feature?
- How far does “plan” extend — lodging and food, or activities only?
- What does the outfitter-side coordination look like for multi-day holds?
Interested in this one? If you're living this problem, want to build it, or just want to compare notes — message me on LinkedIn or book a day and let's scope it.