You know what I really like? TripIt.com. It's amazingly simple. You take all those travel confirmation emails that you get from your travel agent, hotels, car rental agencies, etc, and you just forward them to email@example.com. That's all you have to do. You don't have to sign up for an account. You don't have to log on. You just forward those emails. You can do it right now.
You get a link back by email, with a beautifully organized itinerary, showing all your travel data plus maps, weather reports, and all the confirmation numbers for your flights and address for your hotels and so on.
It's kind of magical. You don't have to fill out lots of little fields with all the details, because they've done a lot of work to parse those confirmation emails correctly... it worked flawlessly for my upcoming trip to Japan.
Think of it this way. Suppose you want to enter a round trip flight on your calendar. The minimum information you need to enter is probably:
All in all it takes a few minutes and is very error prone. Whereas, with TripIt, you just take that email from the airline or Orbitz, Ctrl+F, type firstname.lastname@example.org, and send. Done.
TripIt is a beautiful example of the Figure It Out school of user interface design. Why should you need to register? TripIt figures out who you are based on your email address. Why should you parse the schedule data? Everyone gets email from the same 4 online travel agencies, 100-odd airlines, 15 hotel chains, 5 car rental chains... it's pretty easy to just write screen scrapers for each of those to parse out the necessary data.
Anyway, it's a shame I have to say this, but I have no connection whatsoever to tripit.com.
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