I'm using TripDeck on my iPhone to sync trips from TripIt. The data in TripDeck only downloads from TripIt when I am at home. Most of my travelling is by train and neither TripIt or TripDeck are good with trains - for example, neither of them include which platform the train is leaving. I've contacted the support people at TripDeck and they say they will add this information in the future.

For maps, I use OpenMaps on my iPhone. When I am at home, I simply download maps of all the cities I will visit and I use the "pin" feature to place a pin on the map for my hotel or other places I need to go.

I also keep copies of email confirmations on my iPhone. A few weeks ago, I picked up train tickets after reserving on the Internet and the agent forgot to print out one ticket. Since the confirmation email (with booking number) was also on my iPhone, I showed it to the conductor and he confirmed it by telephone. This was very convenient.