Cayo Hueso. Skull Island. Thompson’s Island. The End of the Road. Margaritaville. Fantasy Island. The Conch Republic. All of Key West’s many names evoke images of swaying palm trees, aquamarine waters, ice-cold beverages, and a laid-back island lifestyle. There’s something for everyone here: a colorful history, a vibrant arts community, super shops, fabulous food, legendary watering holes, the only living coral barrier reef in North America, and a captivating kaleidoscope of wildlife—on land, at sea, and especially on Duval Street.
For centuries, quirky residents and artists have been drawn to Key West’s secluded beauty. Even after a railroad connected the Florida Keys to the mainland in 1912 (followed by the highway in 1938), the town remained a bastion of easy-going independence. Today, Key West is renowned for its liberated spirit and community of freethinking individuals.
The city’s zany appeal is highly apparent in Mallory Square, where street vendors, performance artists, and local artisans entertain the crowds that gather by the waterfront. The main thoroughfare, Duval Street, is lined with shops, art galleries, bars, and restaurants. Souvenir shops with zany window displays compete for attention with a collection of high-end jewelry and specialty boutiques proffering an array of shiny objects. Island-themed items, artisan crafts, and eco-friendly resort wear are available at every turn. Look for Key West Aloe in the area—for nearly 50 years, it has used a base of the highest-quality aloe vera in each of its skin-care products to nourish, hydrate, and protect.
Just a block from Mallory Square is the redbrick terra-cotta Custom House, home of the Key West Museum of Art & History. The landmark building was the government center during Key West’s lucrative shipwrecking era, when it was the richest city, per capita, in the United States. Visitors can stand in the very room where US officials made the decision to go to war with Spain after the sinking of the USS Maine battleship—a perfect prep for the jolt of eclectic, electric experiences that Key West has in store.
Within walking distance of the Custom House, historic attractions, homes, and gardens continue to tell the story of Key West’s unusual past. The architecture is an intriguing mix of Victorian mansions and brightly hued gingerbread cottages, many of which have been transformed into museums or bed-and-breakfasts, thanks to the efforts of local foundations.
Key West’s most famous residence is The Ernest Hemingway Home & Museum, now an interactive museum for literary enthusiasts. From 1931 to 1940, the Nobel Prize-winning author lived in this Spanish-colonial-style estate, where he enjoyed some of his most productive years. In fact, many Key Westerners appear as characters in Hemingway’s novel, To Have and Have Not. Today, visitors can tiptoe up the stairs to see Hemingway’s office. His desk, chair, typewriter, and wall ornaments are supposedly just as the celebrated eccentric author left them. And, as many as 60 descendants of his beloved cat Snowball still lounge around the tropical grounds.
The Audubon House and Tropical Gardens is an elegant mid-19th-century example of American classic-revival architecture. The home was built by Captain John H. Geiger, Key West’s first state-licensed harbor pilot. Geiger made his fortune as a master wrecker, salvaging ships that floundered on the key’s treacherous reefs. Now the house provides a perfect setting for the original works of John James Audubon, the world-renowned ornithologist, who visited the Florida Keys in 1832. While painting in the property’s tropical gardens, Audubon identified and drew 22 species of Florida birds.
The waters around Key West once claimed one ship per week on average, the remnants of which can be found at several local museums. The Mel Fisher Maritime Museum is a repository of the richest collection of 17th-century sunken booty in the Western Hemisphere. It’s also a hub for the excavation and preservation of nautical artifacts, with an emphasis on early Caribbean history and the Florida Keys.
More treasures recovered from these wrecks are on display at the Key West Shipwreck Museum, which has been modeled after the warehouse of 19th-century master wrecker Asa Tift. A must-see here: original cargo from the most profitable wreck in Key West history, the 137-foot-long Isaac Allerton, which sank in 1856.
Artists and wreckers weren’t the only ones who found sanctuary on Key West. Former president Harry Truman also caught “Keys Disease.” Immediately after World War II, he turned a former naval base into his vacation headquarters and used it as a winter home for the remainder of his time in office. Now a landmark, the Harry S. Truman Little White House is a living museum where government functions and meetings are held to this day.
To sit back, relax, and tour the port town’s highlights, choose between Old Town Trolley Tours and the Conch Tour Train; both have depots in Mallory Square. The Old Town Trolley, which touts itself as, “the attraction that takes you to the attractions,” offers a 90-minute narrated tour covering some hundred points of interest. The Conch Tour Train, rolling since 1958, features wisecracking guides who provide a signature “conch’s-eye view” of the attractions. A special one-hour nonstop tour is a great way for cruise guests to make the most of the day in port.
Both tours head down Duval Street to what is likely the most photographed site in Key West: a concrete monument marking the southernmost point of the United States. Who wouldn’t want a picture taken with the enormous buoy that marks a spot that’s closer to Cuba than to the US mainland? Just one block north of this legendary landmark is the Key West Butterfly & Nature Conservatory where visitors can walk among hundreds of living butterflies and colorful birds.
Visitors can acquire a different sense of Key West’s former residents at the oddly amusing Southern Keys Cemetery. Above-ground granite crypts are joined by headstones etched with epitaphs such as, “I told you I was sick,” and, “At least I know where he’s sleeping tonight.”
The only living coral barrier reef in North America protects the coast from the pounding waves of the Atlantic Ocean, thereby preventing natural sand creation. Although the beaches are somewhat rocky, the reef makes Key West a fishing and diving mecca. Chock-full of exotic fish, the Florida Keys National Marine Sanctuary protects 2,900 square nautical miles of water surrounding the Florida Keys. Within the area are the world’s third-largest barrier reef, extensive sea-grass beds, and more than 6,000 species of marine life. Thousands of shipwrecks scattered along the reef add to the international allure.
Key West’s seafaring legacy lives on at the revitalized Historic Seaport District and the Key West Bight Marina, known to locals simply as the Bight. Scores of shrimp boats used to call this marina home, although now its docks are full of vessels offering everything from snorkeling trips to fishing charters. Guests can partake in plenty of water-bound activities, such as kayaking, paddleboarding, parasailing, or even sailing on a historic schooner.
Check out the Key West Aquarium to observe marine life without getting wet including tropical angelfish, parrot fish, tarpon, green sea turtles, and several bonnethead sharks.
Seafood is the king of Key West cuisine. Locally caught Florida spiny lobsters, stone crabs, and yellowtail snapper are only a few of the local delicacies. Conch, another Key West specialty, is particularly scrumptious served as a fritter or in a spicy chowder. No visit is complete without a taste of key lime pie—lip-smacking yellow custard in a graham-cracker crust. Stop by Kermit’s Key West Lime Shoppe for a chocolate-dipped Pie on a Stick. It’s just one of the many out-of-the-box treats that make Key West so uniquely delicious.