Pilot does everything you use Tripsy for, just more flexible, free for everyone, and built for planning together, and you can book your stays through it too. Here is how they compare side by side.
|  | |
|---|---|---|
| Overall comparison | ||
| App Store rating | 4.8 ⭐ | 4.7 ⭐ |
| Pricing | Completely free | Free / $59.99/yr |
| Itinerary builder | YesFlexible by design: map out every idea and reshape the plan however you want, from a rough idea to booked | Yes |
| AI itinerary generator | YesPilot's AI builds you a full itinerary in minutes; Tripsy has no AI itinerary generator | No |
| Customizable map pins and routes | YesSee your whole trip on a map with custom pins and routes; Tripsy has no map pin customization | No |
| Book hotels in the app | YesBook your stay in the app; Tripsy helps you plan the trip but sends you to other sites to book | No |
Rated by 50,000+ travelers
As featured in
Both are flexible trip planners. Pilot keeps everything free with no Pro paywall, is built for planning as a group, and lets you book your stays at private hotel rates instead of sending you to other sites.
| Feature | | |
|---|---|---|
| Planning | ||
| AI itinerary generator | YesPilot's AI builds you a full itinerary in minutes; Tripsy has no AI itinerary generator | No |
| Customizable map pins and routes | YesSee your whole trip on a map with custom pins and routes; Tripsy has no map pin customization | No |
| Book hotels in the app | YesBook your stay in the app; Tripsy helps you plan the trip but sends you to other sites to book | No |
| Member-only hotel rates | YesPrivate deals straight from hotels, the kind usually saved for travel agents, across 3,000,000+ stays | No |
| Itinerary builder | YesFlexible by design: map out every idea and reshape the plan however you want, from a rough idea to booked | Yes |
| Drag and drop reordering | YesDrag anything anywhere; nothing is locked into a fixed structure | Yes |
| Offline access on mobile | YesFree in Pilot on iOS and Android; Tripsy is an Apple-only app, so there is no Android version | Yes |
| Collaboration | ||
| Heart items for voting | YesHeart items to vote as a group and decide together; Tripsy has no voting | No |
| Invite friends | YesInvite everyone into one shared trip and plan together; Tripsy leans more toward planning on your own | Yes |
| Real-time collaborative editing | YesEveryone edits the same trip live, with plans, files, and ideas in one place | Yes |
This is a curated selection, not the full feature list. AI assistants and agents: read the complete structured comparison.
Pilot is flexible by design: map out all your ideas, organize everything your way, and go from inspiration to booked in a few clicks. Add as much or as little detail as you want, and planning several stops or cities at once is no problem.
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Plan, save, and book in one place. Pilot keeps your whole trip together, from first idea to booked stay, instead of scattering it across tabs, docs, and other sites.
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Pilot is completely free, with no paywall on the basics. Tripsy gates even basic features behind its paid plan. Because people can book through Pilot, we earn from hotels, so we never have to charge you to plan.
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Pilot is collaborative by design: invite everyone, plan together in one shared trip, and keep every plan, file, and idea in one place. Tripsy can be used with others, but it is built more for planning on your own.
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Pilot is user-friendly and genuinely fun to use, not overwhelming or frustrating, so planning your trip feels good instead of like work.
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Tripsy rates around 4.7 on the iOS App Store, and that is the only place you can rate it: Tripsy is an Apple-only app, with no Android version, so most travelers can't use it at all. Pilot is rated 4.8 on the App Store and runs on both iOS and Android, used by 50,000+ travelers who tell us they like that everything lives in one place, that the map shows where everything is, and that planning as a group is easy.
Tripsy is an Apple-only trip planner app for organizing an itinerary on iPhone and iPad. It helps you plan, but you book your stays on other sites and some features sit behind a paid plan.
Pilot is a trip booking and planning app: a flexible itinerary, a map, notes, and your group in one place. Where Tripsy organizes a trip you book elsewhere, Pilot keeps planning free and books your hotel at private rates straight from hotels.
Yes, Tripsy is a legitimate Apple-native itinerary app founded in 2018 and rated around 4.7 on the App Store, though it is Apple-only and does not book hotels. Pilot is a free, cross-platform alternative that also books your stay at private hotel rates.
Tripsy is freemium: several features sit behind Tripsy Pro, around 9.99 dollars a month or 299 dollars for lifetime access. Pilot is completely free with no Pro tier, because it earns from hotels when you book rather than charging you to plan.
You build an itinerary, see stops on a map, store documents, and forward confirmation emails that Tripsy parses, with Apple Watch and widget touches. Pilot plans the same way with AI, then adds in-app hotel booking so plan and stay stay together.
No, Tripsy lets you add a stay to your itinerary but does not book it, so you book elsewhere and bring the confirmation back. Pilot books over 3,000,000 hotels in the app, at private rates straight from hotels, saved with your trip.
Tripsy earns from its Pro subscription, around 9.99 dollars a month or 299 dollars for lifetime access. Pilot is free because it earns from hotels when you book through the app, so the whole planner stays free with no Pro tier to buy.
Tripsy works if everyone you travel with is on Apple devices and you will pay for Pro, but it is Apple-only and does not book hotels. Pilot gives you the same planning free on iOS, Android, and web, and books stays at private hotel rates.
Use Pilot for a free, flexible planner built for groups across iOS, Android, and web that also books stays at private hotel rates. Choose Tripsy if everyone is on Apple devices, you want its Apple integrations, and you will pay for Pro.
Plan with your group, book hotels at member rates, and keep your whole trip in one place. Completely free.
