Road Warriors: TripIt, TripIt Pro Keep Tabs on Your Every Move

This past week, I've been putting together the itinerary for our family vacation. My two oldest children live in different cities and I need to document all the arrangements so that they will each know what is going on and when they need to get on airplanes. I finally got around to using a service I signed up for months ago and I am totally hooked -- TripIt. This is an amazing resource for vacation planners and road warriors like me -- and it even has a social networking component.

I signed up for TripIt because a colleague sent me an "invite" (think "friend request") several months ago. I was reluctant to sign up for one more social networking application but I did it anyways because the invite came from Brian Ocheltree, someone who has, on more than one occasion, introduced me to something or someone really helpful. Was I totally interested in knowing where Brian was every time he traveled (which is what the social network part is all about)? Sorry, Brian, but not particularly. Then I got another request from a colleague I trust so now I'm connected to two people and still not seeing much value in knowing where they are each week. I got a promotional email this week, however, and it triggered something as I realized it was getting close to vacation time and I still haven't completed documenting our itinerary.

I had started long Word document listing all our flights, confirmation numbers, dinner reservations, and hotels. We're staying in four different hotels and celebrating two birthdays during the week we're away so between the airlines, the hotels, the special dinners, and the car rental, the trip is getting pretty complicated. That's where TripIt comes in and this is where it is so cool. I took all of my e-mail confirmations - from hotels booked with award points and special "extra" bonus awards and one that I actually paid for, from dinner reservations confirmed by, and from airline confirmations and e-mailed each individual confirmation to As long as the confirmation came from the e-mail address I used to register with TripIt, each confirmation landed in an itinerary TripIt created for the vacation and pretty much all of the information landed in the correct spot. Instant integrated itinerary! Moreover, I was able to manually add some of the events that we're doing (a couple major league baseball games) and TripIt calculated the directions from the airport to the hotel and from the hotel of the moment to the stadium or restaurant - all in one place online but also in a very convenient printed format. Yes, we'll bring our GPS on the trip, but it's helpful to know about how much time it will take to travel to and from our various destinations.

What makes this site even better, however, is that I can share the itinerary with my older kids and my father so that the kids will be able to see what is going on and my father will know how to reach me in an emergency. Brian O. will also know when I leave and return but not necessarily the details of the trip unless I choose to share them with him.

I was successful e-mailing a confirmation from Delta, which comes as an .html attachment, airline confirmations from Southwest and Frontier, hotel confirmations from Westin, Hyatt, and Hilton, a car rental from Priceline, and an entire itinerary from Orbitz (which is how I booked my trip to the SharePoint conference in October). I decided to give TripIt a test to see if it would be able to process an itinerary from the travel booking service that one of my clients has me use and that worked even better. For some of the flights, it failed to capture my frequent flyer number or seat assignment but the itinerary from went in perfectly. The only thing that stumped TripIt was a confirmation for a flight I booked with Starwood Points. That came in as a "note" that I was able to copy and paste into the itinerary.

I also signed up for TripIt Pro, which they are offering at half price ($49.00/year) if you sign up by July 31, 2009. All the other features I just mentioned are free and fantastic. But TripIt Pro is where it gets especially fun for road warriors like me. One feature I like is that you can enter all your frequent flyer and hotel reward numbers and see a consolidated list of your activity and points in one place. I've got most of mine entered but it will take me another sitting to get them all in. TripIt Pro also tracks your flights and can send you an alert if there is a delay or a gate change. I know that the airlines pretty much all do that, but what they don't do is let you know what alternate flights are available if your flight gets delayed or cancelled. I could have used this feature on Friday night when my Northwest flight was delayed by close to 3 hours. Fortunately, I knew that US Airways flies the same route at the same time so when I got the alert from NWA that the flight was delayed, I called them and asked them to book me on the US Airways flight - which they did. TripIt Pro would have given me that information and give me alternate flight options on Northwest, plus options from all other airlines - and how many seats are available on each alternate flight. While I could definitely get this information from other sources for free, this is definitely worth $49/year to me.

My only regret about TripIt is that I didn't start taking advantage of the functionality sooner! While the social aspect of the software is interesting, it's the ease of compiling itineraries and sharing them with all the people who need to see them - at work and at home - that has me hooked. Now, if it would only pack and unpack for me too ...

This story, "Road Warriors: TripIt, TripIt Pro Keep Tabs on Your Every Move" was originally published by Network World.

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