TripIt

If you do a reasonable amount of travelling, TripIt is super handy of keeping an overview of your itineraries, tickets, etc.

As I'm about to embark on a ten-day train trip through Europe, I am having to keep track of 4 different hotel reservations and at least 8 different train reservations. 

This all seemed a bit daunting, but I'll tell you what: I forwarded all the tickets for the reservations to TripIt and it "magically" figured out most of my itinerary for me. While TripIt definitely is better with air travel I was impressed with the information it could gather from the train tickets as well. I did have to upload each individual ticket unfortunately, but in the end that's a small job for a huge trip.

Promotional screenshot of the TripIt mobile interface with a fictional itinerary opened

I feel quite privileged to be able to travel as much as I do, both for work and privately, so I know this app is not for everyone. But if you are about to embark on a trip with more than a single city destination then I would recommend you trying it.

Pro (paid) options are to get airline updates and possible better seating options. I'm sure that works fantastically in the USA, but not in Europe, in my experience.