hit the road, jack
In travel, as with everything else, prior planning is clutch, so allow me the humble pleasure of introducing you to Duffle:
Duffle lets you plan out every aspect of your upcoming trip(s). Just put in the basic trip information to start (when, where, etc) and Duffle creates an individual trip profile to assist in all your planning needs, it even makes suggestions on where to stay and what to do once you're there. It also gives you plenty of organizing space to do things like write yourself reminder notes, categorize your activities, and keep track of your transportation plans.
If you're like me, and you've decided to forego flying in favor of a road trip with friends from out of town, consider using MeetWays to find your starting point.
Say your point of departure is in the Land of Pleasant Living but your road trip companion is coming from the land of ice and snow and the two of you have to meet in the middle before you can hit the road, MeetWays can help you find your starting place. Just enter both starting addresses or zipcodes and MeetWays will give you your halfway point. You can even specify what kind of place you'd like to meet, for example: a coffee shop, a diner, or a hotel (if it's more of a romantic rendez-vous).
But no matter where you go, or how you get there, you'll need some sweet tunes once you arrive. That's where pulpTunes comes in.
Just download pulpTunes and you'll be able to connect with your home iTunes collection no matter where you are. As long as you have internet access you'll be able to have a dance party in Instanbul or play DJ while visiting friends on the Cape. At the very least you'll be able listen to some clandestine 504 Boyz while you're at work, but that's not nearly as exotic.
Happy trails, amigos.