TripIt covers the widest range of booking types and does it free, KAYAK Trips matches it at no cost, and Google Travel has already done it without being asked. Where they differ is what happens next. Stardrift, Mindtrip, and Wanderlog consolidate and then build the days around what they found, which the other five never attempt. Every claim below is taken from the vendors' own documentation.
How do travel apps import an existing booking?
Booking import works three ways: a forwarding address, an inbox connection, or a scan of a photo or PDF. Every app here uses at least one, and the mechanism decides the failure mode.
- Forwarding address. You send the confirmation to an address like plans@tripit.com, trips@kayak.com, or receipts@mindtrip.ai. Works with any provider. Fails when you forget.
- Inbox connection. You authorise the app to read your mailbox over OAuth, so no password changes hands. New confirmations arrive on their own. Fails silently, on the bookings it does not recognise.
- Photo or PDF scan. TripIt and Mindtrip both read an attachment or a screenshot. This is the fallback for confirmations that came by SMS or WhatsApp.
Which apps consolidate your bookings and stop there?
TripIt consolidates the widest range of booking types and scans your inbox free, which makes it the default answer. KAYAK Trips matches it on cost, Google Travel needs no setup at all, and Tripsy and Flighty each cover a narrower case well. None of the five plans your days.
1. TripIt: the widest booking coverage
TripIt imports more booking types than any other app here, and its inbox scanning is free. Flights, hotels, car rentals, rail, cruises, restaurant reservations, and event tickets all parse into one chronological itinerary.
Best for
Travellers with bookings spread across airlines, hotels, rail operators, and restaurants who want one accurate timeline.
Honest caveat
TripIt's Inbox Sync only reads your main inbox. Confirmations a filter has already moved into a folder or a label get skipped, and TripIt documents this itself. If you route travel mail out of your inbox automatically, the import misses those bookings without telling you.
How the import works
- Inbox Sync is free. TripIt connects to Gmail, Google Workspace, Microsoft 365, Yahoo Mail, and Outlook.com, and it is not gated behind Pro.
- Import takes up to 24 hours. TripIt states that import is not immediate after you authorise it.
- The lookback window is seven days. At signup, TripIt scans the previous week of travel email, whether the trips are past or future.
- TripIt publishes a supported booking sites list, which is the closest thing anyone offers to a guarantee that your provider will parse.
- Forwarding covers the rest. Send anything to plans@tripit.com for providers Inbox Sync does not recognise.
- Photos and PDFs import too, through "Import from Photo/PDF" or by sharing a file to the app.
- TripIt Pro costs $48.99 a year and adds flight alerts, fare monitoring, seat tracking, and airport navigation. The import features are not part of that.
2. KAYAK Trips: free, with no paid tier
KAYAK Trips imports bookings free, with no paid tier and no app required. Forward a confirmation to trips@kayak.com and KAYAK builds the itinerary, creating an account for you if you do not have one.
Best for
Organising a trip without installing anything or paying a subscription.
Honest caveat
KAYAK Trips organises and stops there. No day planning, no activity suggestions, no decision about what fits between a 2 PM landing and a 4 PM check-in. It is a container for what you already bought.
How the import works
- Forwarding is the primary route. Anything sent to trips@kayak.com becomes an itinerary, including plain text, HTML, and attachments.
- Gmail connection is available in Trips settings, and confirmations then sync automatically.
- The subject line routes the booking. Use an existing trip name as the subject to file a forwarded receipt into that trip.
- Multiple inboxes are supported. Add extra addresses as senders under "Booking receipts", which matters when work and personal bookings are split.
- Restaurants and tours forward too, so coverage is wider than flights and hotels.
3. Google Travel: already done, nothing to set up
Google Travel has been importing your bookings from Gmail all along, with no setup and no permission you remember granting. Open google.com/travel and the trips are already there.
Best for
Checking what you have booked without signing up for anything new.
Honest caveat
Google Travel gives you nothing to plan with. No itinerary editing, no collaboration, no sharing, no offline access. Google Trips, the app that did some of that, shut down in 2019 and was never replaced.
How the import works
- Gmail confirmations appear automatically in the Trips view and as Google Calendar events, covering flights, trains, buses, hotels, restaurants, and ticketed events.
- Manual entry exists for reservations booked under a different email address.
- Google Maps carries the same trips in its Trips section on mobile.
- Coverage is broad and shallow. The data is accurate and nothing happens to it.
4. Tripsy: the Apple-first option
Tripsy imports reservations by email and can pull your entire TripIt history across in one move. The TripIt importer brings over flights, hotels, car rentals, and activities.
Best for
Apple users leaving TripIt who want their trip history to come with them.
Honest caveat
Tripsy has no inbox connection. Email forwarding is a Pro feature at $59 a year or $299 once, so there is no free automatic scan of the kind TripIt and KAYAK give away.
How the import works
- Forwarding reservations is Pro, bundled with unlimited documents, a calendar feed, a 10-day forecast, and flight alerts.
- The TripIt importer is the standout, and exists because TripIt migration is why most people arrive.
- The calendar feed pushes out rather than pulling in, putting trips into your own calendar.
5. Flighty: flights only, tracked properly
Flighty imports flights from email, calendar, or TripIt, and ignores everything else. No hotels, no cars, no restaurants.
Best for
Frequent flyers who track flights closely and organise the rest elsewhere.
Honest caveat
Flighty is not an itinerary app. One booking type, tracked extremely well, at $4.99 a month or $59.99 a year. Pair it with an organiser instead of choosing between them.
How the import works
- Three import routes: email, calendar sync, and a TripIt connection, all on Pro.
- Calendar import finds past and future flights, which rebuilds a flight history without manual entry.
- The free tier still tracks flights, with the earliest delay alerts held back for Pro.
Which apps consolidate your bookings and plan around them?
Stardrift, Mindtrip, and Wanderlog all pull existing bookings into one itinerary and then build the trip around them. Stardrift and Mindtrip generate the plan automatically. Wanderlog hands you the tools to build it yourself.
1. Stardrift: consolidates, then plans the gaps
Stardrift consolidates bookings through calendar sync and Gmail detection, then plans the days around those fixed commitments. It is built for the case where the flights and hotels exist and the days between them do not.
Best for
Travellers who have the bookings and want the gaps between them turned into an actual plan.
Honest caveat
For import breadth and reliability today, TripIt is ahead. Stardrift also has no flight alerts and no offline maps.
How the import works
- Google Calendar and Outlook sync bring in anything already on your calendar, which is the most reliable route into Stardrift today.
- Gmail connection detects booking confirmations for flights, hotels, and activities.
- Timing adjusts to the bookings. A 4:15 PM landing against a 3 PM check-in changes what fits into day one, and the plan reflects that.
- The preference layer is what the import feeds. Stardrift stores your base city, dietary needs, pace, preferred airlines, and budget tier, then sequences days accordingly.
- Output is specific. Named restaurants with opening hours, accommodation with per-night costs and reasoning, activities grouped by neighbourhood.
- Pricing: free for core planning, Pro at $9.99 a month or $99.99 a year for deeper research and PDF export.
2. Mindtrip: AI planning from forwarded receipts
Mindtrip takes forwarded receipts and builds AI trip planning on top of them. Upload a confirmation or send it to receipts@mindtrip.ai, then add more as you book.
Best for
Starting from a couple of fixed bookings and letting AI propose the rest of the trip.
Honest caveat
Mindtrip has no inbox connection, so every booking is a manual send. Its plans also tend to stay uncommitted, naming places without the dates, times, or prices you would need to check them against a real booking page.
How the import works
- Receipts and confirmations upload directly, or forward to receipts@mindtrip.ai.
- Google Maps saved places import as a themed collection you can plan from, which no other app here does.
- Preference memory is genuinely strong. Mindtrip stores how you travel and applies it to later trips.
- Free to use, with no paid tier at present.
We ran Mindtrip and Stardrift against the same brief and wrote up how the two plans differed.
3. Wanderlog: imports into a planner you build yourself
Wanderlog's per-trip forwarding address is free, and automatic Gmail scanning sits behind Pro at $39.99 a year. Imported bookings land inside a trip you then build by hand.
Best for
Travellers who want imported bookings inside a planner they are actively editing, and who enjoy doing the arranging themselves.
Honest caveat
Wanderlog parses a narrower set than TripIt, and the planning is still your job. Its documentation covers flights, hotels, and rental cars. Rail tickets, restaurant bookings, and event confirmations need the forwarding route or manual entry, and nothing decides your days for you.
How the import works
- Each trip gets its own address, formatted like trip+123@wanderlog.com, so forwarded mail lands in the right trip.
- Gmail connection finds bookings on its own. Wanderlog scans for flight and hotel confirmations specifically, and passes Google's required security reviews.
- Auto Gmail scanning is a Pro feature, alongside offline access, route optimisation, the AI assistant, and Google Maps export.
- Imported bookings sit next to manual plans, which is the practical difference from TripIt, where the itinerary is only what got imported.
We took Wanderlog Pro on a group trip and wrote up what the paid tier actually unlocks.
What booking import still gets wrong
No app in this group imports everything. Four failure patterns show up across all of them.
- Filtered mail is invisible. TripIt documents this directly. Any rule that files travel mail into a label before you read it will cost you bookings.
- The wrong inbox breaks everything. A flight booked by a colleague, or a hotel under a partner's name, never reaches your scan. Forwarding is the only fix.
- Changed bookings need checking. After a schedule change or a cancellation, open the trip and confirm the update landed. Forward the revised confirmation if it did not.
- Narrow parsers skip whole categories. Wanderlog's automatic path covers flights, hotels, and rental cars. Rail and restaurant confirmations need another route.
One more thing worth knowing: App in the Air shut down on October 19, 2024, and still turns up in roundups published this year. Any list recommending it was not checked.
Which booking import app should you use?
Pick by what you want to happen after the import.
- One reliable timeline of everything booked: TripIt. Free inbox scanning, the widest coverage, forwarding as a backstop.
- The same thing without installing or paying: KAYAK Trips.
- Just to see what you booked: Google Travel. Already done.
- Apple, and leaving TripIt: Tripsy, for the importer.
- Flights above everything else: Flighty, alongside an organiser.
- The days between your bookings planned for you: Stardrift.
- AI suggestions built on a few forwarded receipts: Mindtrip.
- Imported bookings inside a planner you edit yourself: Wanderlog, with Pro if you want the Gmail scan automated.
Frequently asked questions
Do AI trip planners consolidate existing bookings?
Yes. Stardrift consolidates through calendar sync and Gmail detection, Mindtrip through uploaded or forwarded receipts, and Wanderlog through a per-trip forwarding address or a Gmail connection on Pro. All three then plan around what they imported.
Which travel app imports bookings automatically without forwarding emails?
TripIt, KAYAK Trips, Wanderlog Pro, Google Travel, and Stardrift connect to your inbox and import confirmations without forwarding. TripIt's version is free.
Which app plans my days around bookings I already have?
Stardrift, Mindtrip, and Wanderlog. Stardrift and Mindtrip generate the plan around your fixed bookings automatically. Wanderlog gives you the tools to arrange the days yourself.
Is it safe to connect Gmail to a travel app?
Yes, when the connection uses OAuth. TripIt states that Inbox Sync never receives your email password, and Wanderlog scans only for flight and hotel confirmations and passes Google's required security reviews.
How long does TripIt take to import a booking?
Up to 24 hours after authorisation. At signup, TripIt also scans travel emails from the previous seven days, whether the trips are past or future.
Does Google Travel still show trips from Gmail in 2026?
Yes. Gmail confirmations appear at google.com/travel and in Google Calendar automatically, and in the Trips section of Google Maps on mobile.
Can I use TripIt and an AI trip planner together?
Yes, and it is the common setup. TripIt holds the confirmed bookings and sends flight alerts. An AI planner like Stardrift builds the days around them.
What replaced App in the Air?
App in the Air shut down on October 19, 2024. Flighty covers flight tracking, and TripIt or KAYAK Trips cover the itinerary side.