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Pilot Group trip planner and booking app

Sources checked .

Free group trip planner with an AI itinerary builder and bookable stays

  • You book in the same app

What is Pilot?

Pilot is a trip planning and booking app for groups and solo travellers, with collaborative itineraries, maps, document storage, checklists and group chat. Its free AI itinerary builder creates plans from a prompt and filters, an AI chat gives recommendations, and AI can add forwarded files to your itinerary. Hotels, hostels and rentals can be booked through Pilot, which also arranges group room blocks.

Cost: Free (No paid plan listed). Booking: You book in the same app. Works on: Web, iPhone, Android.

Best for: Friends or families planning a group trip who want shared plans and group hotel rates in one free app.

How Pilot uses AI

Generates itineraries from a prompt and filters, gives tailored recommendations in chat, suggests activities, and parses forwarded documents into the trip.

Booking: You book in the same app.

Keep in mind

  • The iOS listing describes the app as an early release
  • Full-service group planning is a separate paid service for organisations

Is Pilot free? Cost and plans

Free. 'Our app is always free.' Pilot says it earns from optional bookings and premium services. Full-Service Planning for organisations costs $49 per attendee per night.

Pilot alternatives

Tools for a similar task. Sharing a task does not make them interchangeable, so compare what each one does.

Sources

Sources checked . This listing summarises what the provider and other cited sources say; it is not a hands-on test.

  1. Free Trip Booking and Planning App | Pilotpilotplans.com, checked . Supports: AI itinerary builder, AI chat recommendations, AI document import; stays from over 3.2 million partners confirmed directly with the hotel; group room blocks; free
  2. Pilot pricingpilotplans.com, checked . Supports: App always free; AI QuickStart Itinerary Generation and AI Activity Suggestions; iOS and Android apps; Full-Service Planning $49 per attendee per night
  3. Pilot: Group Trip Planner (App Store)apps.apple.com, checked . Supports: iOS app by Happyhour Services Inc., early release, free with no in-app purchases, updated 2026-09-30
  4. Pilot: Group Trip Planner (Google Play)play.google.com, checked . Supports: Android app, updated 28 Sep 2026
What we could not confirm
  • AI usage limits not stated
  • Accommodation supply partners not named

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