A genteel gem on Florida's Paradise Coast, Naples sits on the Gulf of Mexico, with seven miles of white sand beach fanning out around downtown's old-fashioned pier. Naples has had the good fortune to charm one wealthy patron after another since it was settled in the late 19th century, and it's evolved from a sandy bay backed by swampland to a prosperous, bustling resort city with nearly 40 golf courses, ample shopping, and a thriving arts scene. It has a plenitude of galleries, plus the highly reputed Naples Museum of Art and Naples Philharmonic Center for the Arts. Annual events include the Naples International Art & Antique Fair. The local hotels represent the very top tier of luxury brands: Ritz-Carlton, Waldorf Astoria, and Naples Beach Hotel & Golf Club.

Yet for all its civilized charms, Naples remembers the vast, untamed outback that surrounds it. It's the gateway to the Everglades and offers every conceivable Everglades excursion and nature tour. Swamp buggies and airboat rides are two of the more unusual ways to see the surrounding area. It's also the jump-off point to explore the Ten Thousand Islands—the closest being Marco Island just to the south—and offers access to some of Florida's best fishing.