Tripsy vs TripIt: Which Trip Planner Fits You in 2026?
Tripsy is the polished iPhone planner, TripIt the free email organizer on iPhone and Android. What each does free, what Pro costs, and which to pick.
By NomadPoint · Nov 7, 2026 · 7 min read
Scan with your iPhone camera to get the appTripsy and TripIt do the same basic job: they hold every booking for a trip in one itinerary. The difference is what you pay for it and what kind of phone you carry.
The short answer:
- If you want your bookings organized for free, pick TripIt. Forwarding confirmation emails is part of its free plan. In Tripsy it needs Pro.
- If you only use Apple devices and care how the app looks and feels, pick Tripsy. It runs on iPhone, iPad and Apple Watch, and one Pro purchase covers your family.
- If you use Android, it's TripIt. Tripsy has no Android app yet.
- If you want flight alerts, both charge for them: $49 a year for TripIt Pro, $59 a year for Tripsy Pro.
- If you want the trip and what comes next in one app, look at NomadPoint (we make it, details below).
Every price and feature below comes from each company's own pricing and help pages, checked on 7 November 2026.
What each app does for free
TripIt free
TripIt's free plan is built around email. Forward your confirmations to plans@tripit.com, or turn on Inbox Sync, and TripIt builds one itinerary out of flights, hotels, rental cars, trains and even restaurant bookings. Its pricing page lists the rest of the free plan:
- Itinerary on every device, with calendar sync
- Transport options, nearby places, neighborhood safety scores and airport maps
- Flight compensation eligibility (through AirHelp), carbon footprint and travel stats
- 3 uploaded documents per trip
It has apps for iOS, Apple Watch and Android, and the same page says you can open your itinerary offline. Nothing live is included for free: real-time flight alerts are Pro.
Tripsy free
Tripsy is free to download. According to the comparison table on tripsy.app/pro, the free plan includes unlimited trips, cloud sync, unlimited guests and flight search. You add flights, stays and activities yourself.
What's missing is the automatic part. Forwarding reservations by email, Smart Import (turning files, links and text into plans), documents, flight alerts, expenses, the calendar feed, the 10-day weather forecast, time-zone changes and data export are all marked Pro.
What you pay for
| TripIt | Tripsy | |
|---|---|---|
| Pro price (US) | $49 a year | $59 a year or $299 lifetime |
| Free trial | 30 days | Not listed |
| Forward booking emails | Free | Pro |
| Documents | 3 per trip free, 25 with Pro | Pro |
| Calendar sync | Free | Pro (calendar feed) |
| Travel stats | Free | Pro (advanced stats) |
| Expenses | Not listed | Pro |
| Flight delay and gate alerts | Pro | Pro |
| Check-in and "Go Now" reminders | Pro | Not listed |
| Fare refund and seat tracking | Pro | Not listed |
| Import from the other app | Not listed | Pro (TripIt importer) |
| Family sharing of Pro | Not listed | Yes |
| Android app | Yes | No (web viewer only) |
Sources: TripIt pricing, TripIt Pro features, Tripsy Pro, What's included in Tripsy Pro, Tripsy for Android.
TripIt Pro is $49 a year after a 30-day free trial. It adds real-time flight alerts, terminal and gate reminders, a check-in reminder 24 hours before the flight, a "Go Now" nudge to leave for the airport, risk alerts, alternate flights, fare and seat trackers, reward program tracking, walking directions to your connecting gate, baggage claim info, a passport renewal reminder and 25 documents per trip.
Tripsy Pro is $59 a year or $299 once for life, and both are shareable with family. Its help center lists what you get: expenses in several currencies, unlimited document storage, forwarding reservations by email, flight alerts for gate changes, departure and arrival times and baggage claim, advanced travel stats, the 10-day forecast, time-zone changes, a calendar feed, a daily TripIt import and export to text or CSV.
How they differ in practice
You notice the difference the first time you book something.
With TripIt you forward the hotel email and you're done, for free. The same itinerary opens on an Android phone too.
With Tripsy on the free plan you type the hotel in yourself. It's a carefully designed app, with versions for iPhone, iPad and Apple Watch. But the thing most people want from a trip organizer, bookings showing up on their own, sits behind the $59 Pro plan.
On alerts, it's close. Both send flight changes only with Pro. TripIt Pro goes further around the airport, with check-in reminders, "Go Now", gate directions and fare tracking. Tripsy Pro is more about the trip itself: expenses, documents, weather and stats.
If you're already on TripIt and want to try Tripsy, Tripsy's TripIt importer signs in to your TripIt account from Tripsy's settings and pulls your plans across. It's listed as a Pro feature.
Which one should you pick?
Pick TripIt if you want bookings organized without paying or you use Android. Pay for Pro only once you want flight alerts, check-in reminders or fare tracking.
Pick Tripsy if you live on Apple devices, you're happy to pay for Pro, and design matters to you. The lifetime option and family sharing make it cheaper than it looks if several people in one household travel.
Skip both Pro plans if all you need is a list of your bookings. TripIt free already does that.
A third option: one app that knows what's next
NomadPoint, the app we make, is a travel planner for iPhone, iPad, Mac and Apple Watch. It keeps flights, stays and activities in one journey and shows what comes next, for example the train after you land and then check-in at the apartment.
How it lines up against the two:
- Like TripIt free, forwarding booking emails to build the journey costs nothing. You can also import from your iPhone calendar, Tripsy, TripIt, Flighty and Google Maps lists.
- Unlike Tripsy free, documents, expenses, weather and time-zone changes are free.
- It checks visa and entry rules for your passport at every stop and counts Schengen 90/180 days. Neither TripIt nor Tripsy does that.
- NomadPoint Pro adds flight delay, gate and cancellation alerts, a Live Activity on travel days and alerts before a visa or stay allowance runs out. It has none of TripIt Pro's fare, seat or reward tracking.
- There's no Android app.
NomadPoint Pro is $47.99 a year or $7.99 a month in the US (see pricing).
Moving over? We have side-by-side pages for Tripsy alternatives and TripIt alternatives, and direct comparisons of NomadPoint vs Tripsy and NomadPoint vs TripIt. If flights are what you care about most, read TripIt vs Flighty, and for a wider list see the best travel planning apps.
Frequently asked questions
Is Tripsy better than TripIt?
Tripsy is the more polished app on iPhone, iPad and Apple Watch. TripIt does more for free, mainly turning forwarded booking emails into an itinerary, and it works on Android. If you won't pay for Pro, TripIt is the stronger choice.
Is Tripsy free?
Yes, with unlimited trips, guests and flight search. Forwarding booking emails, documents, flight alerts, expenses and the calendar feed need Tripsy Pro, at $59 a year or $299 lifetime.
Can Tripsy import from TripIt?
Yes. In Tripsy's settings, choose TripIt Importer and sign in to your TripIt account. Tripsy lists TripIt import as a Pro feature that updates daily.
Does Tripsy work on Android?
Not as an app. Tripsy's Android page says there's no native app yet. You can view your itineraries in a browser at my.tripsy.app, but you create and edit trips in the Apple app.
Which is cheaper, Tripsy Pro or TripIt Pro?
TripIt Pro is $49 a year and Tripsy Pro $59 a year in the US. Tripsy also sells a $299 lifetime plan and lets you share Pro with family, which TripIt doesn't list.
Your whole trip, and the next step, in one place. NomadPoint builds the journey from your bookings for free, watches your flights with Pro, and already knows what comes next. Free to download.
NomadPoint Team
Written by nomads who've lived in 30+ countries. We build the tools we wish existed.
