TripIt vs Pilot

TripIt8.9Visit Pilot8.5Visit

Higher score TripIt #4 in Travel Itinerary Apps 8.9/10 Free plan · 30-day trial Free planFree trial✓ 5 of 5 features Visit TripIt

vs

Pilot #8 in Travel Itinerary Apps 8.5/10 Free plan Free plan✓ 4 of 5 features Visit Pilot

• TripIt fits best

  Reliable booking-to-itinerary organization

• Pilot fits best

  Free AI-assisted itinerary planning

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Side by side

Feature	TripIt 8.9/10 Visit ↗	Pilot 8.5/10 Visit ↗
At a glance
Editor score	8.9	8.5
Ranking	#4 in Travel Itinerary Apps	#8 in Travel Itinerary Apps
Best for	Reliable booking-to-itinerary organization	Free AI-assisted itinerary planning
Pricing model	Free plan + paid	Free
Starting price	—	Free
Free plan	✓	✓
Free trial	30 days	—
Deployment	Cloud, Mobile	Cloud, Mobile
Platforms	Web, iOS, Android	Web, iOS, Android
Support	Email, Tickets, Docs	Email, Live chat
Built for	Solo, Small business, Mid-market	Solo, Small business, Mid-market, Enterprise
Features TripIt 5/5 · Pilot 4/5
Reservation import	✓	✓
Route planning	✓	✓
Shared itineraries	✓	✓
Offline access	✓	✓
Calendar sync	✓ (best)	Not checked yet
Specs
Trip limit	Not checked yet	Not checked yet
Primary platform	Web	Web
Our review
Pros	Automatically builds itineraries from forwarded booking confirmations Supports sharing, calendar feeds, offline access, and document storage Available on web, iOS, and Android with major calendar integrations	Entirely free core plan with no annual charge Imports reservations, files, screenshots, and forwarded emails Combines collaboration, route planning, AI, and offline mobile access
Cons	TripIt Pro costs $49 per year after its advertised 30-day trial The public API is no longer available for new integrations The free plan allows three document uploads per trip	Offline access is limited to the iOS and Android apps Paid add-ons and premium services are separate from the core product Accommodation booking and discovery may not suit travelers wanting itinerary planning only
Our verdict	TripIt organizes flights, hotels, rental cars, trains, activities, and other travel plans into a single itinerary. It is designed for leisure and business travelers who want booking confirmations, reservation details, maps, directions,… Read the review →	Pilot is a web and mobile travel planning app for solo travelers, groups, and teams. It combines a flexible drag-and-drop itinerary builder with map pins, route planning, reservation imports, shared editing, trip invitations, AI-generated… Read the review →

Strengths and trade-offs

• TripIt — where it wins

  • Automatically builds itineraries from forwarded booking confirmations
  • Supports sharing, calendar feeds, offline access, and document storage
  • Available on web, iOS, and Android with major calendar integrations

  Where it doesn't

  • TripIt Pro costs $49 per year after its advertised 30-day trial
  • The public API is no longer available for new integrations
  • The free plan allows three document uploads per trip

• Pilot — where it wins

  • Entirely free core plan with no annual charge
  • Imports reservations, files, screenshots, and forwarded emails
  • Combines collaboration, route planning, AI, and offline mobile access

  Where it doesn't

  • Offline access is limited to the iOS and Android apps
  • Paid add-ons and premium services are separate from the core product
  • Accommodation booking and discovery may not suit travelers wanting itinerary planning only

• TripIt8.9/10 · Free plan · 30-day trial

  A capable booking-to-itinerary organizer with useful free features and a $49 annual Pro tier.

  Visit TripItFull verdict →
• Pilot8.5/10 · Free plan

  A fully free itinerary planner with booking imports, collaboration, maps, AI, and offline access.

  Visit PilotFull verdict →