The bulk of my travel is for business, and of that travel, a lot of it is on complicated itineraries. Sometimes I'll do a swing of the East Coast and visit three or four cities, I'm frequently jumping between hotels, and I often have rental cars to deal with, too.
All these reservations are a pain in the butt to manage, which is why I've become an avid user of TripIt.
TripIt is an online trip planner that basically takes all your reservations and automatically (and with very little effort from the user) puts them into one place.
Here's how it works: You know how when you make an air, hotel, or rental car reservation, you get an email confirmation with all the details? Once upon a time I used to print those out and carried them with me in a file folder. Now, I just take those emails and forward them on to TripIt. They have a software engine (they call it their "Itinerator") that reads the email and puts all the pertinent information into a custom built itinerary.
Here's an example of how I use TripIt.
1. I'm traveling to Chicago and Boston in late March/early April. First, I booked plane tickets on AA.com. Because of some intricacies of my plans, I actually booked three one way tickets: LAX-ORD, ORD-BOS, and BOS-LAX. When AA.com sends me my email confirmations, I forward all three to plans@tripit.com. (I do the same for my hotel and rental car reservations in both cities.)
When you sign up for TripIt, it learns your email address. That way it knows that email confirmations forwarded from me should go into my account. (In my case, TripIt actually knows both my work and personal email addresses, so no matter which I use to send TripIt my plans, it puts them in my account.)
2. I can now log into TripIt.com, where I can see that my account now has in it a trip to Chicago and Boston. I click on that trip, and there I can find all my reservations, including confirmation numbers, dates, and times. TripIt's software knows which city I'll be in on which date (because it knows how to read my reservations), so it also compiles all the weather forecasts for each day in each city, as well as links for maps from the airport to the hotel.
3. Over the course of the next few days, I continue to build my itinerary. I make a restaurant reservation on OpenTable.com for one of the days I'm in Chicago, and book theatre tickets for an evening in Boston. I also realize I have to see a client in New Haven, CT during the time that I'm in Boston, so I book a train ticket on Amtrak. In all those cases, I forward my email confirmations to TripIt. (And when I log onto the site, I can see all those plans conveniently filed in the proper order in my itinerary.) I also make a few meetings with some clients in Boston and New Haven. Though I don't have official email confirmations for those meetings, I can enter them by hand into my TripIt itinerary.
4. The next bit of magic happens in the days before my trip. TripIt provides every user with a custom .ics calendar feed to which I can subscribe using my calendar software (in my case, that's Google Calendars). By subscribing to that feed, my calendar automatically shows all my trips, as well as all the individual pieces within those trips (flights, hotel check in and check out times, rental car drop off times, restaurant reservations, etc.). You can actually customize that feed to provide your calendar with just the information that you want.
This isn't just useful for my own calendar. I've also given that feed address to my boss and to my wife. That way, they can see my travel plans, too.
5. TripIt gets really useful on the day of travel. First, if you're a low-tech kind of person, you can use TripIt to print out a single master itinerary of your whole trip. Instead of having to sort through a whole sheaf of papers with all your confirmations, you can carry just one sheet of paper with everything in one place.
My preferences are a little more, um, electronic. I have TripIt's free iPhone app on my phone (they also make apps for Blackberry and Android smart phones), which allows me to have easy access my itineraries at my fingertips. When I get into the rental car and fire up my GPS, I can pull up my TripIt itinerary on the iPhone to get the address of the hotel (if your smart phone has a GPS, you can even click on the address to map it right). If I'm at the airport, I can pull up my flight reservation to see departure and gate information, links to learn more about an airport, and phone numbers (click to call) for the airline. TripIt offers even more features to Pro members, including the ability to instantly search for alternate flights (with options for multiple airlines, and information on seat availability).
TripIt has a bunch of other features that I don't use so much. They can track your point balances from a number of award plans. They have a social networking feature that allows you to see friends' travel plans. (This would be useful for Ryan Bingham and Alex Goran for planning a romantic rendezvous. The TripIt software could automatically tell them when they're next going to be in the same city.) They also have some cool partnerships with other travel tools (Yapta, for example) that add lots of functionality.
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