Is TripIt Really the Best, Or Just the First?

Trips, even small trips, require significant planning, and all of the requisite paperwork.

Booking confirmations, receipts, e-tickets, maps, website urls, travel insurance information, addresses, phone numbers, dates and times – the list of important information to preserve and have easy access to goes on and on.

Of course, the longer/more complex the trip, the more paperwork involved.

Amy of the Slow Travel Talk forums would like to know how others manage all of this travel information:

I was wondering how others organize the details of their complex travels. I keep my trip emails … in separate email folders. … to double-check everything I make post-its of the details, and arrange them onto a board so I can check lodging dates with deposit and balance info, transportation details, tours I might book, to-do lists, and see what might be missing. I tie everything together with Tripit to have an online source of all the info as I travel, and also print out that document.


Always looking for better ideas–how do you do it?

Based on the replies so far it seems most travelers prefer some combination of the following methods to manage their trip planning data:

  • Google products (Gmail, Google Drive, Google Docs, Google Sheets)
  • Non-Google cloud-based and file sharing solutions like Microsoft OneDrive, iCloud, DropBox, etc
  • TripIt
  • Files saved directly on a laptop and/or printed and stored in a physical binder

Needless to say, all of these methods have their pros and their cons. And the discussion is really informative as travelers share their various methods in detail, and the reasoning behind them.

What really caught my attention though was the almost unanimous support of TripIt.

I don’t say that to imply that TripIt doesn’t deserve the kudos. But no one – not one person who has replied on this thread to date – even mentions Kayak’s My Trips app, TripCase, WorldMate, or any other trip planning app.

Amongst those participating in this discussion at least, TripIt appears to be the only trip planning app worth using.

TripIt is undoubtedly a great app and serves many thousands of travelers well every day. And it was the first truly enterprise-class app launched in its category.

Still, it’s dominance in this discussion is somewhat surprising. While being first to market is no doubt important, it’s also relatively rare that being first to market with regard to travel applications results in long term market dominance – especially when big boys like Kayak and Sabre decide to enter the fray.

I would be curious to hear what ThreadTripping readers think about this. Is this just a case where the sample size (one discussion thread) is too small to draw any conclusions, or is TripIt still the leader by a substantial stretch in the trip planning application category?

And do you use any trip methodologies not mentioned in the thread?

Read the thread in its entirety: How Do You Prefer to Organize Travel Details?

TripIt logo courtesy of



  1. When I still had a Blackberry, I used Blackberry Travel. Now I use TripIt after switching to an iPhone. I prefer Blackberry Travel, especially it’s auto-loading function – travel confirmations automatically forwarded to Blackberry Travel for creation of, or addition to, trip itineraries. TripIt promises something similar (periodic inbox scanning), but rarely have I gotten it to work. After emailing them for help, they simply suggested that I forward confirmations to them manually, which indicated to me that they haven’t been able to get the programming to work properly or consistently. Their mapping/directions also don’t work well all the time and some obscure airlines aren’t covered. Otherwise I’m pretty happy with the service. Note: I get the upgraded version for free through a rewards card or some other third party membership; I’m not sure the free service is very worthwhile.

  2. First to market is huge. I’ve been using Tripit for years. Never tried any of the other apps – I get Tripit Pro with my Barclay Arrival+, and it does everything I need, including automatically updating itineraries, seat alerts, and sharing trips with my team and family. Perhaps I don’t know what I’m missing, but I’m very happy with it.

  3. I’ve been using it since I first heard of it. I’ve been experimenting with TripCase lately just because my employer’s travel agency is a Sabre agent. Work itineraries auto import into TripCase. It’s semi-handy. I like the way TripCase looks. But alas, when it gets down to it, TripIt can import a cruise line itinerary, and TripCase can’t. Same for Worldmate, which is also a pretty good program, unless it’s changed since I last tried.

  4. I prefer Kayak’s MyTrips vs Tripit, mostly because it offers some features free that Tripit charges you for, namely flight alerts that tells you delays/baggage claim info/connecting flight info. It also allows you to create a private calendar feed, so that once everything is forwarded and read, it’ll pop up on your calendar.

    I’m sure there are other features in TripIt Pro that may be useful, but not useful enough for me to pay $50/y for, instead of free.

  5. Tripit just frustrates me but I keep using it:
    – It doesn’t handle cancellation emails
    – It doesn’t handle schedule changes even when you email a new confirmation, with the same code.
    – It doesn’t know that you cannot check-in before you land and so books hotels stays out of order of flights based on check-in time and not possible arrival times

  6. just saw this article through Zite…I am a TripIt user also for years. Why have I not tried others? Why should I? Tripit works well and has since day 1. Improvements have really been improvements and not just added features to justify the paid version. It works reliably well all the time. If it didn’t and hadn’t from the beginning, perhaps I would have tried others.

  7. I did use the free version TripIt but I wasn’t crazy about the changes they made and I dint want to pay for the pro version. So I switched to Kayak and love it. Everything is in one place. I get alerts to check in and on flight status. I usually get delay info from them before it comes in from Delta! And it’s free.

  8. Interesting to see how many like the Kayak app. And KFM, thanks for the info about BlackBerry Travel. I had never heard of that one before but it sure sounds like it was ahead of its time and suffered mightily from BlackBerry’s fall from grace.

  9. I had no idea all these other options existed so I’ve just been using tripit for years. I gave TripCase and Kayak a chance and imported my next three trips into them.

    Tripcase had trouble importing some of my flights. I’m not sure if it is because it was an award booking or because it was for two people. But both tripit and kayak imported it fine. Tripcase also didn’t find the reservation number from a hotel import. It was nice that it included information about the plane type and gate info. But, if it messed up this much off of three trips, I don’t think it’s for me.

    Kayak has worked fine so far at importing and looks so much better than tripit. It doesn’t have all those adds on the side and has a much cleaner feel overall, especially since it doesn’t try to show directions to everything. It also seems to order things much better than tripit. The only downside I see is that tripit shows you were your friends are and notifies you if you and a connected friend are traveling and your paths cross. But so often the shared itineraries on tripit didn’t work so that’s a push.

    After all of this, I’m going with Kayak but I’ll check on the others periodically and see if things change. Thanks again for bringing all of these to my attention.

  10. I’ve tried others but always come back to TripIt. Really wish they would add game or sporting event under activity though, seeing that’s the main reason I travel. Asked them about it, don’t think they understood what I was asking. It is a pain to edit long itineraries though, always goes back to the top.

  11. I told a couple of my friends about my switch to Kayak and they wanted to know why. After a couple different times a decided to just write a blog post on it and save myself some time. The short answer is that kayak and Tripit work best and Kayak looks so much better it makes it an easy decision. You can find that post (including pictures) here if you’re interested:

  12. I agree, Kayak has improved a lot recently: better import of itineraries, the scanned copy of your email with all the details, status updates, better user interface. I’ve grown to like it. Only downside is the lack of social features/sharing.
    Worldmate is similar to TripIt, Tripcase has too many problems with importing itineraries properly.
    I compared the four options in detail here:

  13. Tripcase consistently has problems importing travel itineraries. Tripit imports easily. That matters.

  14. It’s been about a year since I checked out all the options and decided I liked kayak best, as discussed in my comment above. They’ve all had a few updates since then so I redid my comparison of TripIt and Kayak. The good news is that TripIt has fixed the ordering so it really just comes down to aesthetics and which features you prefer. I still prefer Kayak but you can read a more thorough review here:

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