2. Naples, Florida

Credit the romanticism of promoters in the late 1800s, who saw a town much like its Italian namesake, with abundant fishing, the temperate climate on the Gulf of Mexico, and a view that surpassed the Bay of Naples in its grandeur. This lively town lives up to its international reputation.

With rich cultural offerings (including resident orchestral and theater groups), this town of just fewer than 20,000 people offers big-city-pay-offs minutes from beaches with some of the finest snowy white sand in the region. A strong arts community has kept the downtown scene as beautiful as the shoreline. Shopping mavens love to scout for antiques and artisans finds at Tin City, an open-air marketplace. Always a center for fresh seafood, the town as undergone a recent culinary boom. And with so much within reach of its neighborhoods, it's one of the most walkable cities on our list.

Where to Stay: The boutique Inn on Fifth is blocks from the beach in Old Naples, with plush pillow-top beds, a spa, and more than 20 nearby restaurants. Rates start at $159; 239/403-8777 or innonfifth.com.