Pilot

Pilot, at pilotplans.com, is a trip planner that also books stays. The honeymoon page on October 31, 2026 says you chat with AI for honeymoon and anniversary ideas, save a shared shortlist, and invite a partner to edit it. The FAQ on that page says Pilot is free to use with no hidden fees, and that optional premium services and add-ons, particularly for groups, are how it is funded. The same FAQ says the AI can generate a first draft itinerary, which you then edit. The pricing page the same day says the app is always free, shown at $0 a year, and that optional add-ons and premium services are for large groups and businesses. A retreat offer on that pricing page is a different product: a planning fee of $49 per person per night, and optional on-site staffing from $150 an hour with an 8-hour day minimum. The honeymoon page links to the App Store and Google Play. A stay booked in Pilot is still a hotel reservation. Read the total and the cancellation terms before you pay the hotel.