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Poised between the Gulf of Mexico and the Everglades, Naples belies its wild setting with the trappings of wealth—neo-Mediterranean-style mansions, neatly manicured golfing developments, revitalized downtown streets lined with galleries and one-of-a-kind shops, and a reputation for lively and eclectic dining. Visitors come for its luxury hotels—including two Ritz-Carltons—its fabulous white-sand beaches, fishing, shopping, theater and arts, and a lofty reputation for golf. Yet with all the highfalutin living, Naples still appeals to families, especially with its water park and the Golisano Children’s Museum of Naples.

Old Naples, the historic downtown section, has two main commercial areas, 5th Avenue South and 3rd Street South, and there’s also a small cluster of restaurants right by City Dock on Naples Bay. Farther north on U.S. 41 (the Tamiami Trail, or 9th Street here), hotels, shopping centers, and developments have fast been filling in the area around and south of Vanderbilt Beach, including the dining and shopping meccas Waterside Shops, and the Village on Venetian Bay.

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