Tripsy vs TripIt Pro Pricing: Which to Buy

Tripsy Pro costs $59 for a year or $299 once for lifetime access, and TripIt Pro costs $49 a year. Both figures were read off tripsy.app and tripit.com in September 2026 from a US connection, and both are higher than the numbers most comparison posts still quote. The choice between them is not really about the $10. TripIt is a post booking service: you book somewhere else, forward the confirmation, and TripIt Pro spends the year sending you flight alerts, gate changes, seat options and fare refund notices. Tripsy is a planning and record keeping app: it holds the trip, the expenses, the documents and the people coming with you, and it sells one price that a family can share. If you fly often for work and want a safety net on travel days, buy TripIt Pro. If you plan trips with other people and want one app that holds everything, buy Tripsy, and buy the lifetime tier if you expect to travel for more than five more years.

Below is what each one actually charges in 2026, what the free tiers cover, a head to head on the things that differ, the one claim about Tripsy that almost every comparison gets wrong, and a straight answer on which to buy.

Tripsy vs TripIt: what is the actual difference?

TripIt sits after the booking. You forward a confirmation email, or connect your inbox, and TripIt builds a master itinerary out of it. That itinerary is the free product and it is genuinely good: flights, hotels, cars and restaurant bookings in one dated list, on the phone and on the web, with a calendar feed and a few documents attached per trip. Everything TripIt Pro adds happens on or near the travel day. TripIt is owned by SAP Concur, which is why the Pro page carries a link asking whether you use Concur, and it is also why TripIt is the app most often reimbursed by an employer.

Tripsy sits around the trip. It holds the itinerary too, but it also holds expenses in multiple currencies, documents, notes, photos, web links, and the guests you invite, with per guest permissions so a collaborator can edit the plan while a view only guest just sees flight times. It keeps a travel log of countries, hotel nights and flying hours. Tripsy is made by Tripsy LLC, a small independent developer, and it shows in the design and in the pricing model.

That is the split worth paying for. TripIt Pro is insurance against the trip going wrong. Tripsy Pro is a container for the trip and everyone in it. They overlap on the itinerary and diverge on everything else, which is why plenty of frequent travelers end up paying for both and why most people only need one.

How much does Tripsy Pro cost?

Tripsy publishes two prices on tripsy.app/pro. One Year is $59 and buys a year of Tripsy Pro. Lifetime is $299 as a one time purchase. Both are marked shareable with family, which matters more than it sounds: one purchase covers the household, so a couple planning together pays once.

The $39.99 figure you will see quoted on comparison sites and in older reviews is not invented. The App Store listing for Tripsy still shows a set of in app purchase SKUs that includes a $39.99 annual tier and a $7.99 monthly tier alongside the $59.99 annual and family options. What the current pricing page sells is $59 a year or $299 for life. If you are budgeting from a review written a year ago, budget the higher number.

The free tier is not a trial and is more generous than most people expect. Tripsy free includes unlimited trips, cloud sync across devices, unlimited guests on a trip, flight search and expense management. You can plan an entire trip, share it with four people and track what everyone spent without paying.

Pro adds the automation and the archive. Tripsy Pro imports your reservation emails when you forward them, turns files, links and pasted text into travel plans through Smart Import, pulls useful details out of documents with Smart Insights, sends flight update alerts for gate changes and delays, stores and manages documents, publishes a calendar feed, shows a 10 day weather forecast and timezone changes, keeps advanced travel stats, and exports your data as an activities list or itinerary.

How much does TripIt Pro cost?

TripIt Pro is $49 a year, billed annually, with a 30 day free trial first. TripIt states it plainly on its own Pro page: start the free 30 day trial, then it is $49 for a year. The trial requires a payment method and converts automatically, which is the single most common complaint about TripIt in app store reviews, so put a reminder on day 27 if you are only testing it.

Free TripIt is permanent, not a trial, and it already does the thing most people install TripIt for. It builds the master itinerary from forwarded confirmations, reads bookings out of a connected inbox, syncs the trip to your calendar and stores up to three documents per trip.

The $49 buys sixteen additions, and every one of them starts working after the booking exists: real time flight alerts, fare refund monitoring that flags when a fare drops enough to claim a credit, seat tracking and alternate flight finding, a go now prompt that tells you when to leave for the airport, airport terminal and walking directions, gate and baggage claim updates, reward program point tracking, and a higher document limit of 25 per trip. The full breakdown is on the TripIt Pro cost page, including what the trial charge does and does not let you refund.

Tripsy Pro vs TripIt Pro compared

Is Tripsy only available on iPhone?

No, and this is the fact most comparisons get wrong. Tripsy started as an Apple only app and is still described that way in reviews, roundups and Reddit threads written as recently as last year. Tripsy now ships Tripsy for Web and Tripsy for Android alongside the iPhone, iPad, Mac and Apple Watch apps, and lists both on its own site.

That kills the cleanest tiebreaker people used to rely on. If half your travel party is on Android, that used to decide the question outright in TripIt's favor. It no longer does, and if you passed on Tripsy for that reason more than a year ago, the reason has expired.

Tripsy also ships one thing TripIt does not: direct import from TripIt and from TripCase, built into the product. TripCase shut down, which sent a wave of business travelers looking for a replacement, and Tripsy built an importer for both. Moving a trip history out of TripIt into Tripsy is a supported path rather than a copy and paste weekend.

Which is better for business travel?

TripIt, in most cases, and the reason is not the feature list. TripIt is owned by SAP Concur, and if your employer runs Concur, TripIt Pro is often provided to you at no personal cost through TripLink or an employer program. Paying $49 for something your travel policy already covers is a bad trade, so check with whoever administers expenses before you buy anything. The SAP Concur free trial page covers how that relationship works and what TripLink customers get.

Beyond the Concur connection, the case for TripIt on work trips is the travel day. Business travel goes wrong on a schedule: a delayed first leg, a gate that moves, a missed connection that needs a new flight before the desk agent gets to you. TripIt Pro finds the alternate flights and pushes the gate and baggage updates, and on a trip where a missed meeting costs more than the subscription, that is $49 well spent.

Tripsy earns its place on a different kind of work trip: the consultant with expenses in three currencies, the small team traveling together, the founder who needs a defensible record of what was spent and where. Tripsy tracks the expenses natively and lets everyone on the trip add their own, which is the part TripIt hands off to an expense platform. If the trip is built around meetings rather than flights, the app that holds the schedule matters less than the tool you use to book the meetings around your flight times in the first place, and neither of these apps tries to do that.

Is Tripsy or TripIt worth paying for?

TripIt Pro is worth $49 if you take more than roughly six flights a year, or any long haul with a connection. Below that, free TripIt does the organizing and you are paying $49 for a safety net that may never be needed. Above it, one rebooked connection returns the money.

Tripsy Pro is worth $59 if you want reservation emails imported for you and documents held in the app, and it is worth $299 if you expect to keep traveling for five more years, because the lifetime tier breaks even at year five and is shareable with a partner, which halves it again in practice. If you plan one trip a year and do not mind adding flights by hand, the free tier is genuinely enough and you should not pay anything.

The honest case against both is that neither is what people usually mean when they say they need help planning a trip. Both assume the trip already exists. The TripIt alternatives page covers what to use when the plan itself is the missing piece, and Wanderlog vs TripIt covers the comparison people reach for when they want a planning canvas rather than an alert service.

Can you move your trips from TripIt to Tripsy?

Yes. Tripsy has a built in Import from TripIt path and a separate Import from TripCase path, both listed on its site, so your trip history moves across rather than being rebuilt. That is worth knowing before you renew a TripIt subscription out of inertia, because the usual reason people stay on TripIt is the archive rather than the product.

Going the other way is harder. TripIt does not offer an importer from Tripsy, so a move in that direction means forwarding confirmations again for the trips you care about. If you are unsure, run Tripsy free alongside TripIt for one trip. The free tier holds unlimited trips, so nothing stops you from testing it properly.

What neither app does

Neither Tripsy nor TripIt decides what the trip contains, and neither prices it before you commit. TripIt starts when a confirmation exists. Tripsy starts when you know where you are going. Between "we have a week in October and about $3,000" and the first booking sits the work that actually eats the evenings: which cities, in what order, how many nights in each, what the days contain, what all of it costs, and whether the whole thing fits the budget.

That is the half TripAgent.ai does. You give it the destination, the dates, the party, the total budget and the kind of trip you want, and it writes a day by day itinerary with morning, afternoon and evening blocks, a price on every line, travel times between stops, and a total for each day and for the trip. Ask it to rewrite Thursday because the museum is closed and it redrafts and reprices that day. It does not book anything, so once the plan is settled you book it yourself and forward the confirmations to whichever of these two apps you bought. The itinerary maker page shows what a priced day looks like, and the weekend trip planner page covers the short trips people most often try to plan in an app like these and give up on.

Which one should you buy?

Buy TripIt Pro at $49 a year if you fly for work, travel alone or mostly alone, and want the travel day covered. Check first whether your employer already provides it through Concur, and set a reminder before day 30 if you start on the trial.

Buy Tripsy at $59 a year if you plan trips with a partner or a group, keep expenses and documents in one place, and want one purchase to cover the household. Take the $299 lifetime tier only if you are confident you will still be traveling in five years, since that is where it pays for itself.

Buy neither if the trip is still undecided, because that is not the problem either one solves. Plan and price the days first, then pick the app that carries them, and pick it on the travel day question: do you need a safety net, or do you need a container.