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Key West Cruises

Key West, Florida

About Key West

Legendary explorer Juan Ponce de León and his crew of Spaniards were the first Europeans to set eyes on the Florida Keys in 1513, and they called them Los Mártires (the martyrs). A century later, Key West appeared on maps as Cayo Hueso (Bone Key), named for the indigenous bones found on its shores. The British held the Keys for 20 years before ceding them back to Spain in 1783.

In 1821, the US took possession. The city’s first lighthouses were constructed in the 1850s.

During the Civil War, Key West was quickly claimed by the Union, which used Fort Zachary Taylor as its base. As the population grew, so did its industry. Salt, sponges, shrimp, Cuban cigars, fishing and pineapples made this island-city the wealthiest per capita in Florida.

In 1912, the Overseas Railway was constructed to connect the Keys to the mainland. The route was rebuilt as the 128-mile, island-hopping Overseas Highway and opened in 1938, extending a major US highway to this remote paradise. Since then, Key West has increasingly turned its focus to tourism.

During the second half of the 20th century, “pink gold” arrived on the island in the form of succulent Key West shrimp. With its laid-back vibe and beach culture, it wasn’t long before the “Conch Republic” was born, exuding an eccentric flavor all its own.

Key West Lifestyle and Culture

As the southernmost United States city connected by road with the continental US, this fascinating palm-lined enclave is famous for its carefree attitude and festive blend of Caribbean, Latin and American culture.

Visitors can take in the laid-back beach atmosphere at any of the many bars in town, elbow to elbow with the native Conchs (“konks”), a potpourri of free thinkers, artists and bohemians.

On the lively mile-long Duval Street, admire the city’s notable and elegant historic architecture, from old Bahamian style homes to Spanish-influenced Victorian mansions, while Cigar Alley testifies to cultural ties with Cuba. Dozens of inviting galleries dot the streets; strolls along White Street are a staple for any art lover.

The culmination of Key West’s free-spirited atmosphere is the annual Fantasy Fest, held in October. Jovial, body-painted revelers take to the streets and the beaches and gather for a parade through town.

And every night sees a festive gathering at Mallory Square. As the sun goes down, a nightly celebration unfolds to marvel at the fiery red skies, complete with musicians, food vendors and street performers.

Key West Sights and Landmarks

For a charming overview during your free time, take the Conch Tour Train for a 90-minute hop-on/hop-off tour through the Old Town. For a historic glimpse of the seaside haven, explore the landmark homes of some of the city’s most renowned residents.

Visit the Ernest Hemingway Home and Museum, where the literary giant wrote several novels during his most prolific years. Hemingway adopted a white six-toed cat, a gift to him from a ship’s captain. Today, dozens of descendant cats roam about; approximately half of them sport six toes.

At former president Harry S. Truman’s Winter White House, explore his winter residence from 1946 to 1952. Preserved as a national monument and restored in meticulous detail, right down to the wallpaper pattern, it continues to attract history and architecture buffs.

At Audubon House and Tropical Gardens, explore the family home of a well-heeled master wrecker, an old captain who salvaged goods from shipwrecks. Today, the grand house is a gem of the island’s restoration movement, filled with antique furnishings and the art of famed ornithologist John James Audubon, who is said to have identified 18 new birds for his portfolio series during his stay here. Explore the richly adorned house and stroll among the orchids in the gardens.

Key West Entertainment and Activities

People-watching on Duval Street is among the most entertaining ways to experience Key West. But for the best views on the island, climb the 88 steps of the Key West Lighthouse for a spectacular 360-degree panorama and visit the Keeper’s Quarters.

People-watching on Duval Street is among the most entertaining ways to experience Key West. But for the best views on the island, climb the 88 steps of the Key West Lighthouse for a spectacular 360-degree panorama and visit the Keeper’s Quarters.

Marvel at the stunning red-brick and terra-cotta Richardsonian Romanesque architecture of the Custom House, now the headquarters of the Key West Art & Historical Society. The mammoth building, opened in 1891, strikes a dramatic pose among palm-lined streets. Inside you’ll find a fine collection of wood paintings from folk artist Mario Sanchez.

Stroll on Petronia Street to the heart of historic Bahama Village, where the Bahamians first settled. With a colorful Caribbean vibe, the streets are full of hidden gems, from boutiques and eateries to art galleries.

Key West Restaurants and Shopping

It’s no surprise that seafood dominates menus in Key West. Old Town and Bahama Village offer upscale, quality dining. Conch and authentic Key lime pie are two dishes not to miss.

The creative island menu at Louie’s Backyard features specialties such as Florida lobster braised in truffle butter with spinach and prosciutto.

For a flavorful bite of Cuban heritage, El Meson de Pepe is an ideal spot to sip a mojito and enjoy Cuban dishes such as lechón asado, Cuban roast pork in cumin-mojo sauce.

Located in a boutique hotel, Café Marquesa offers elegant dining with fine seasonal and often locally sourced seafood and meat dishes, such as phyllo-crusted mangrove snapper.

For local and Caribbean art, visit Duval between Catherine and Fleming streets, and be sure to explore the unique shops on the side streets. For more specific finds, seek out locally rolled and imported Cuban cigars at Conch Republic Cigar Factory or taste your way through sweet and spicy hot sauces at Peppers of Key West, both on Green Street. Purchase your very own Hemingway novel at Key West Island Bookstore on Fleming Street.