Above: View from Latitudes restaurant at Sunset Key Cottages, Key West, Florida

Improbably, Key West was the richest city (per capita) in the United States in the mid-1800s. Locals would salvage the cargoes of ships wrecked on the shallow reefs surrounding much of the island. The most successful salvagers built grand mansions, many of which still stand to this day. Indeed, much of the city’s old center appears as it did a century ago. These neighborhoods are sharply contrasted by the raucous atmosphere of upper Duval Street, reminiscent of Bourbon Street in New Orleans, lined by souvenir shops, kitschy “art galleries” and margarita-fueled watering holes.

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Above: View from Latitudes restaurant at Sunset Key Cottages, Key West, Florida

Read More from Our Trip:

Three-Hour Tours: Boating in the Keys Marathon’s Marvelous Turtle Hospital Key West Walking Tours Contrasting Resorts in the Florida Keys Favorite Florida Keys Restaurants