I believe the most important parts of trip planning after a place to stay would be dinner plans once you're there, and good reading material and a custom playlist for the trains, planes and automobiles "getting there" bit. When deciding on a vacation destination I have a hard time choosing between old favorites and the most exotic locale I can think of, but I usually end up picking the new adventure. My most recent trip was to Spain. My favorite places that I've visited are Japan and Istanbul, both totally different and totally amazing. For my next next vacation I'd like to check out Buenos Aires or Vietnam.