My e-mail inboxes are like huge digital dumpsters filled with the detritus of ideas, leads, reservations and orders, and a bewildering number of ‘because you did X you might like Y’ solicitations. I go dumpster diving every now and then to fish out some useful bits and unload as much as I can.
In preparation for travel I set up a new e-mail address (see if you can guess it). I use this for all the flight, hotel, car rental, and ferry sites so all my travel related e-mails go to one place. I also send copies of the key documents like passport picture, passport scan, health insurance coverage page and others to this e-mail account (more redundancy to add to the photocopies I carry, the pictures on my phone, the files on my phone and in the cloud). Then I went looking for an app that would automate as much of the organizing as possible.
I ended up choosing TripIt (that evolved out of the business app Concur) and that has been a great choice. Grant it permission to access an e-mail account and it periodically scans for plans, appointments, reservations and adds them to the in app timeline. Like everything useful it takes a little practice to figure out how it all works but the learning curve is steep, and the functionality once you sign up for the ‘Pro’ version is great. In my experience it has captured nearly of my reservations, from flights to hotels to buses to dinners to ballet. Occasionally it will fail to grok some details out, and will flag the item as needing attention. Very occasionally it misses something entirely – I simply forward the confirmation e-mail to Tripit and they sort it out.
Alert settings allow the app to send all sorts of pings to remind about a flight or delays, of if you appear to have conflicting plans or are missing a hotel in on a certain travel leg. The volume can be annoying, so feel free to turn off many so you only get what you want. My favorite was that after that cancelled flight from Gatwick the app flagged it as probably eligible for compensation and also simplified the claim.
You can share trip information by granting access to anyone you think might be interested. This has been especially useful to catch up with other, constantly traveling people. Instead of trading four thousand messages about ‘when and where’ details of possible places to meet, they can just look and see your information on Tripit.
Tripit Pro does make some powerful claims about ‘fare tracking’, ‘points monitor’, and ‘travel stats’. I have found those promises have not delivered, but I am not asking the app to perform those functions.
A little trick I use now for ‘possible plans‘ is to put them in the Notes on my ‘phone, and share that access with any person who has expressed interest in convening. This is great for stuff that is not booked and may or may not happen months in the future (‘6/25~7/6 Toulouse, Carcassonne?’). As plans firm up and evolve it takes only a few seconds to update this note. If anyone is truly trying to catch up with you they can start here.
Additionally, I maintain a spreadsheet of expiration dates of my many credit cards, loyalty points, licenses, permits, passports. I find this much easier to review than searching through a calendar app. It is useful because some of these things require me to be physically present in the US, so it aids me in planning visits there to combine pleasure with admin tasks.