TripIt Beta – Missing the One Feature I Desperately Need from a Digital Travel Assistant

I have been traveling a lot for work this month – I’m on track for something on the order of 25,000 miles in December. I have been looking for a better way to keep track of my various itineraries and travel arrangements. To date, paper has been the best way to go – I just print out all of my confirmations and receipts and stick them in a clear folder. This works great unless you lose your folder or need to quickly and easily share your travel plans with someone else electronically.

So when I heard about TripIt a few months back, I was definitely intrigued. TripIt is a web service that basically builds an itinerary for you — all you need to do is forward any email confirmations you receive to plans@tripit.com and it will intelligently add them to an existing itinerary or create a new trip for you. Once you have the information in TripIt, you can retrieve it by email or over the web. All in all, it’s a nifty way to keep a comprehensive picture of your travel plans.

After using the service for two trips, I have to say the service more or less works but has a few important drawbacks.

What works well

Submission by email works great – TripIt does deliver on its core promise. If you send a confirmation email from a major travel service, it will do a good job of extracting that information and putting it into a comprehensive itinerary. I did find that the service did better with “official” confirmations from airlines than it did with confirmations from 3rd parties like Expedia. I also tried to forward an email that was forwarded to me by someone else who had made my travel plans and it didn’t quite work. I have to believe that this is a tractable problem – as TripIt sees more confirmations and gets smarter about extracting data and creating structure, I expect the quality to improve here.

Calendar integration works really well – It’s not a well-advertised feature, but you can create a simple calendar that keeps track of all of your travel plans. You can then add that calendar to your Google Calendar or Mac calendar and have an overlay that shows your upcoming travel. It’s pretty nifty and useful, especially when I want to schedule meetings around travel.

Areas for improvement

Extracting confirmation numbers and flight numbers are the “killer app” for busy travelers – I was so pleased with my initial experience using TripIt that I didn’t realize that the service was not actually extracting the two things I care most about when managing travel – flight numbers and confirmation numbers. These are the things you need most when things go wrong. It also didn’t include addresses for hotels that I added to my itinerary – these seems like something that could easily be solved via use of a mapping API on the back end. To be truly useful, a service like TripIt needs to have these kinds of features. The main reason to keep track of travel itineraries and such is so you can react when things inevitably go wrong.

Support for updates – I can’t remember the last time I had a business trip where at least one part of my itinerary didn’t change. I haven’t yet been able to test how well the system works. I wonder what happens if I get a new flight and forward it to the service – will it be smart enough to overwrite the old one or will it create a new trip? The ideal thing would be for the service to be able to get those updates itself whenever I make changes.

You must choose your dates carefully – I learned this the hard way. A lot of the intelligence in TripIt seems to come from assigning incoming items to existing trips based on dates. So you have to make sure you have the start and end dates properly configured for any new trips you create. I had one situation where the system extracted the wrong dates and all items I sent in got put into the wrong itinerary. I had to go back and manually move them all to the correct trip.

I haven’t used any of the social sharing parts of TripIt, but those seem interesting as well. I can see a pretty clear business model for this service. One element of the model could be recommendations to complete itineraries (you booked a flight and not a hotel – here’s a recommendation from a paid sponsor or here are the 3 most popular hotels near where you’re staying based on what other TripIt users are doing). A second element could be simply marketing services that web savvy business travelers would enjoy.