Dozen Distinctive Destinations
Key West, FL
Year Listed: 2005
The southernmost tip of Florida and the last in the string of islands known simply as "The Keys," Key West packs a host of attractions on a tiny speck of land, three miles wide by five miles long. Its history, which dates back several centuries to New World explorers, has been influenced by everyone from the rich and famous to humble fishermen, many of them drawn by Key West’s well-earned reputation as a tropical paradise with breathtaking sunsets and vibrant nightlife. While much has changed since author Ernest Hemingway lived here, if you look carefully you’ll still see reminders of the laid-back town that "Papa" Hemingway loved. The author’s Spanish-style home is now a museum and one of the island’s biggest draws - along with Harry Truman’s Summer White House and the Maritime Heritage Museum established by famed treasure hunter Mel Fisher.
This harborwalk allows visitors to stroll along a promenade near local shops and restaurants where they can see historic sailing vessels in Key West’s famous seaport.
Credit: Jimmy Weekley
The Key West Cemetery and its quirky epitaphs - including one that reads "I told you I was sick" - are perfectly in keeping with the island’s off-beat élan. Visitors won’t want to miss a stroll or bike ride along palm-lined streets where they’ll discover gingerbread mansions and tin-roofed "conch" houses. At the end of shop-lined Duval Street, waterside Mallory Square is the site of nightly sunset celebrations. Once the sun makes its final descent, the island moves to a different beat as streets lined with sidewalk cafes, open-air bars and world-class restaurants, come alive. Adored by sports enthusiasts, Key West offers gin-clear waters for swimmers and snorkelers, while scuba divers relish discovering shipwrecks submerged along the Keys coastline.
