In my teens, I never went on vacation without my yellow Sony Walkman. Today's travel gear may be more sophisticated, but the premise is the same: high tech toys that help out when it's time for R&R. When I'm leaving on a trip, I spend hours syncing iPads, iPhones, and eReaders with my media library so I can watch new episodes of AMC's "The Killing," listen to tech podcasts, or read ebooks. But you need fun gear to play all of this digital content too.