Tripsy review

Tripsy is the most refined itinerary keeper on this list. Forward your reservation emails and it lays out flights, stays and activities in one trip, then keeps you posted on flight delays, gate changes and baggage information. Group features are thought through: each guest can be a collaborator or view-only, and you decide whether they see documents and expenses. A favorite guest can be added to new trips automatically. Expenses work in several currencies per trip, and everyone on the trip can add their own. You can store reservations, notes, photos, links and documents per trip and sync everything to your calendar. A free plan exists, and Tripsy Pro costs $59 a year or $299 once, both shareable with family. The trade-offs are price and focus. Pro is pricier than Wanderlog's, and Tripsy is built mostly for organizing what you have booked rather than discovering places. It is designed with Apple users first, although Android and web versions are offered.

Who it is for

iPhone users who want a tidy home for flights, stays, activities, expenses and documents.

Price

Free plan; Tripsy Pro $59 per year or $299 lifetime.

Annual $59 1 year of Tripsy Pro
Quoted from the vendor pricing page on November 9, 2026.

Key features

• Forward reservation emails and Tripsy builds the trip
• Real-time flight updates for delays, gates and baggage
• Guest permissions with collaborator and view-only roles
• Expenses in multiple currencies per trip, with guest contributions
• Calendar feed, document storage and travel stats

Strengths and weaknesses

• Strength: Clean design; Tripsy was an Apple App Store Awards 2024 iPhone App of the Year finalist
• Strength: Pro is shareable with family on both annual and lifetime plans
• Strength: Lifetime option for people who dislike subscriptions
• Weakness: Pro costs more per year than Wanderlog or Roadtrippers Basic
• Weakness: Built mainly for Apple users, though Android and web versions exist
• Weakness: Fewer discovery and map-planning tools than Wanderlog

Key facts

• Free plan: Yes, no subscription required
• Pro annual: $59 per year
• Pro lifetime: $299 one-time
• Family sharing: Yes
• Platforms: iOS, web, Android

Where it ranks

Tripsy is No. 3 in our Best Trip Planner Apps verdict.