You’ll never confuse eight-mile-long Siesta Key, floating off the Gulf Coast below Sarasota and above Fort Myers, with the famed keys south of Miami—and that’s a good thing. This barrier island has long, wide confectionary white sand beaches, the likes of which folks in Key West will only see in their dreams. Though Siesta Key has a definite resort feel, it’s not expensive or overdeveloped, and it's relatively untouched by the Sunshine State's signature blight: millionaire mansions, high-end hotels, and high-rise condos. The best beaches and places to shop and eat are found near the island’s northern tip, in small but bustling Siesta Village. Entertain yourself by fishing, paddleboarding, or kayaking (you can rent equipment from Siesta Sports Rentals).
MUST: The outdoor drum circle that performs on Sunday nights in Siesta Village.
STAY: The Capri at Siesta offers low-priced luxury and kitchenettes in each room, just off the beach. Starts at $149 per day.