Where to go: Northern California, Eastern Florida
Why to go: Coastal breezes, winding roads, and high quality people watching
What to bring: Sunglasses, suntan lotion, and a hat (possibly with straps)

It's nice to get away, but as the saying goes, sometimes it's not the destination, but the journey. If you feel strongly toward this kind of advice, perhaps a road trip is in order to nowhere in particular. The California and Florida coast are two of the nicest parts of the country to rent that convertible that you would never own and take in the sights one mile at a time.