Sarasota

Sarasota

Sarasota is the home of the Ringling Brothers Circus (the museum is wild, and yes, there's a vintage clown college history), and Siesta Key's beach is regularly named the best in America for its pure quartz sand. The cultural scene is heavy for a Florida city of its size (theater, opera, art museum). Gulf sunsets here are the brochure shot. The food scene has caught up to the city's wealth and the retirees' time.

Daytona Beach

Daytona Beach has hard-packed sand you can actually drive your car on (yes, on the beach, it's a tradition). The Daytona 500 brings NASCAR to town every February and shakes the whole city awake. Bike Week is its own beast. Outside of the events, it's a quieter Florida beach town than its reputation suggests, with affordable oceanfront and the Halifax River making the geography interesting.