Short version: TripIt is a natural fit if your main pain is keeping travel reservations organized and getting flight-related updates. Troupe is a better-shaped comparison when the trip is shared and the work includes agreeing on the plan, recording group costs and coordinating the organizer’s checklist.
Two different starting points
TripIt starts with a booking confirmation. Its official instructions invite travelers to forward confirmations to its service, which creates a comprehensive itinerary; the free plan organizes and shares plans across devices. TripIt Pro is listed at $49 per year and adds real-time flight alerts, fare monitoring, alternate flights, check-in reminders, airport navigation and other travel-day assistance. TripIt supports iOS, Android and offline itinerary access.
Troupe starts with the shared trip. The current US App Store listing describes itinerary entries, booking import from the iOS Share Sheet, shared expenses, balances, packing, documents and offline access to locally saved trip details. Invitations use iCloud collaboration, and the listing says invitees can collaborate without each paying for Pro. That is useful when one person is coordinating the group, not necessarily when a solo traveler primarily wants flight disruption alerts.
Feature matrix
| Capability | Troupe | TripIt |
|---|---|---|
| Build an itinerary | Shared group trip and day plan | Automatic itinerary from booking confirmations |
| Import reservations | Share Sheet accepts text, URLs, PDFs and images | Forward confirmations by email |
| Shared expenses / balances | Expense splitting and settle-up within the trip | Not listed as a core feature |
| Group collaboration | iCloud invite workflow; organizer pays for Pro | Sharing plans with others |
| Flight operations | Booking reminders and leave-by context | Pro flight alerts, alternate flights and airport guidance |
| Offline | Saved trip content available locally | Official FAQ says itinerary is available offline |
| Published price | Free starter; US listing $3.99/mo or $29.99 lifetime | Free; Pro $49/year |
TripIt may be a better fit when…
- You travel alone or for work and already have confirmations arriving by email.
- Flight status, seat changes, alternate flights and airport navigation are worth a yearly fee.
- You want a cross-platform itinerary accessible beyond an Apple-only group.
Troupe may be a better fit when…
- The itinerary needs to be shaped collaboratively rather than assembled only from bookings.
- One organizer is also tracking the shared Airbnb, meals, activities and settlement.
- You want the packing list and trip documents beside the plan and costs.
Pricing and source links
TripIt’s official pricing page states $49/year for Pro, while Troupe’s US App Store listing showed $3.99/month or $29.99 lifetime when reviewed on September 12, 2026. Subscription and one-time lifetime plans solve different problems; compare what you will use this year and verify the local checkout price.
- TripIt official pricing and feature matrix
- TripIt Pro official overview
- Troupe US App Store listing
- Wanderlog’s comparison of TripIt and Wanderlog
Plan with the people going
Troupe is free to try for one trip with up to four people. Keep the group plan and the “who paid?” list together.
View Troupe on the App Store →See Troupe features