Disclosure: I may receive a commission for some of the credit card links in this post. I receive no compensation for writing about TripIt and all thoughts and opinions are my own.

I thought I had written before about using TripIt but I guess not. It’s a useful service that has been annoying me a lot lately, so I just wanted to vent here a little bit. TripIt, simply put, is an automated itinerary generator – it “reads” your e-mails and when you get confirmations and the like it will add them to an itinerary for you. This keeps all your reservations conveniently in one place. Now that I’m a dad, my brain has much less capacity to keep itineraries straight in my head so it’s actually something I need. This post will give a short run down on how TripIt is useful and how it is currently annoying me to no end.

TripIt’s Usefulness

Simply put, when working, TripIt is an amazing service. It automatically adds your reservations to an itinerary and keeps them all in one place which is super useful. It also will alert you if there are any conflicting plans. Say you booked two separate flights but the flight times conflict (like one lands after the second departs). TripIt will highlight conflicts in your itineraries and can help alert you to the issue. Here is an example from my latest trip:

My flights are there, seat numbers, layover times, gate (when available), ticket # – lots of stuff you’d want to have while traveling. Thanks to my Barclaycard Arrival Plus World MasterCard® I actually have a TripIt Pro subscription which adds a tiny bit more functionality. It will send you mobile texts about gates, gate changes, and flight changes. That’s pretty useful when your brain is fried, like mine so often is these days.

So overall, TripIt sounds pretty great, right? Right?

Why TripIt is Annoying Me and How I Would Fix It

If you take a look at the screenshot, one of the things that annoys me most about TripIt is right there. There is TOO MUCH information at times. There is no way to turn the itinerary into a bullet list that, you know, would fit on one page. So that’s the first thing that annoys me – the information collected is great, but it isn’t presented in the most user friendly manner.

If that were my only problem with TripIt, then it would just be a nitpick, but my second problem with TripIt is that it’s too good at adding to your itinerary. Any avid award booker will know – you change your itinerary tons of times, sometimes put various itineraries on hold, the airline changes your itinerary, etc. Well every single time that happens, I get an e-mail, and every single time I get an e-mail, TripIt updates my itinerary. So what happens is I get an itinerary with the same five flights on it but all at different times.

Combine this with my first beef – there is no way to look at everything in bullets, so sometimes it’s tough for me to even figure out which flight is the correct one. To figure it out, I need to login to my accounts and figure it out, but that’s work that I want TripIt to do, not me! I literally spent an hour getting my itinerary in order for Brazil before I left and another hour last night doing the same for my upcoming trip to Europe. I wouldn’t mind 15 minutes of housekeeping, after all, I don’t expect TripIt to be Skynet, but an hour is too much in my opinion. Compounding the problem, every time you hit “delete” on a section of an itinerary (handily circled below), the whole webpage refreshes and you need to scroll down again to get to the next section. Again, a bullet list would help so much here – especially a bullet list where you could check multiple sections of the itinerary and delete them all at once.

So yes, TripIt, if you’re listening, here are my requests:

1) Allow us to look at our itineraries in bullet form

2) Allow us to delete multiple sections of an itinerary at once

3) If your autodetectors get multiple versions of a reservation with the same confirmation code, automatically delete outdated ones or ask us or something, whatever is easiest.

Final Thoughts

TripIt is a great service that could be improved. Maybe there are ways to do this – but I haven’t been able to figure it out. If anybody knows, I’d love to hear it. If anyone has a service they prefer over TripIt, please enlighten me (I tried Award Wallet’s itinerary thing but I found it even more cumbersome). If I had to shell out $50 for TripIt Pro I’d be really mad, but it’s tough to complain too much about something that is free. I like the service and just want to see it improve. In the meantime I’ll keep using it until I find a better alternative. Anyone else feel the same way as me?