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.