Key West has long been a magnet for creative souls, adventurous spirits, and those simply seeking a slice of paradise. Its laid-back charm, tropical beauty, and rich history have drawn countless famous figures to call the island home, either permanently or seasonally. From legendary authors and musicians to actors and adventurers, these notable residents have helped shape the vibrant cultural tapestry of Key West. Let’s dive into the lives of some of the most famous Key West residents and their enduring legacies.
Ernest Hemingway: The Literary Icon
No list of famous Key West residents would be complete without Ernest Hemingway. The legendary author moved to Key West in 1928 and lived there for nearly a decade. During his time on the island, Hemingway penned some of his most iconic works, including To Have and Have Not and For Whom the Bell Tolls. His Spanish colonial home on Whitehead Street, now the Hemingway Home and Museum, is a must-visit attraction.
Hemingway’s home is famous not only for its literary history but also for its six-toed cats, descendants of his original feline companions. Visitors can also see the island’s first swimming pool, which Hemingway’s wife Pauline famously installed, costing $20,000 during the Great Depression—a price that led Hemingway to jokingly embed a penny in the concrete.
Jimmy Buffett: The King of “Margaritaville”
Few people have embraced the Key West lifestyle like Jimmy Buffett. The singer-songwriter moved to Key West in the early 1970s, where he found inspiration for his laid-back anthems, including the iconic “Margaritaville.” Buffett’s music and persona encapsulate the carefree spirit of the Florida Keys, and his presence on the island helped cement Key West as a destination for dreamers and drifters.
While Buffett’s main residence is no longer in Key West, his influence remains strong. Fans can visit Margaritaville-themed restaurants and bars and even explore the city with his music as their soundtrack.
Mel Fisher: The Treasure Hunter
Mel Fisher, one of the most famous treasure hunters in history, moved to Key West in the 1960s. Fisher’s determination and adventurous spirit led to the discovery of the Spanish galleon Nuestra Señora de Atocha in 1985. This historic find included gold, silver, and priceless artifacts valued at hundreds of millions of dollars.
Today, the Mel Fisher Maritime Museum celebrates his legacy and showcases artifacts from his discoveries. Fisher’s story of perseverance and success embodies the adventurous spirit of the Florida Keys.
Judy Blume: The Beloved Author
Judy Blume, the iconic author of beloved books like Are You There God? It’s Me, Margaret, calls Key West home. Blume and her husband have lived on the island for years and are active in the local community. They co-founded Books & Books @ The Studios, an independent bookstore in Key West.
Blume’s presence adds a touch of literary prestige to the island, and her bookstore is a haven for readers and writers alike.
Shel Silverstein: The Creative Genius
Shel Silverstein, the celebrated author and illustrator of The Giving Tree and Where the Sidewalk Ends, found solace and inspiration in Key West. Silverstein’s quirky and creative personality fit perfectly with the island’s bohemian vibe. His former home, a converted wood-frame house, is a testament to his eclectic style.
Silverstein’s impact on Key West’s creative scene continues to be felt, as his works remain beloved by readers of all ages.
Tennessee Williams: The Playwright Extraordinaire
Tennessee Williams, one of America’s greatest playwrights, spent more than 30 years in Key West. The author of classics like A Streetcar Named Desire and The Glass Menagerie considered the island his sanctuary. Williams’ modest home on Duncan Street was his retreat, where he painted and wrote.
The Tennessee Williams Museum celebrates his life and work, with exhibits including original manuscripts, photographs, and personal items. Visitors can learn about his deep connection to Key West and his contributions to American theater.
Harry S. Truman: The “Winter White House” Resident
Harry S. Truman, the 33rd President of the United States, spent 175 days of his presidency in Key West at what is now known as the Harry S. Truman Little White House. Truman used the home as a retreat from the pressures of Washington, D.C., and made several key decisions there.
Today, the Little White House is a museum that offers guided tours, giving visitors a glimpse into Truman’s life and his love for Key West’s relaxed atmosphere.
Kenny Chesney: The Country Music Star
Country music sensation Kenny Chesney is another celebrity who has found inspiration in the Florida Keys. Known for his love of the ocean and laid-back lifestyle, Chesney has written numerous songs that reflect the island’s vibe. While he splits his time between various homes, Key West remains one of his favorite retreats.
Chesney’s connection to the island is evident in his music, which often celebrates the beauty and spirit of the Keys.
Kelly McGillis: The Hollywood Starlet
Kelly McGillis, known for her role in Top Gun, lived in Key West for many years. She owned a restaurant on the island and became an integral part of the community. Although she no longer resides there, McGillis’ time in Key West adds a touch of Hollywood glamour to its history.
Truman Capote: The Literary Maverick
Truman Capote, celebrated for works like Breakfast at Tiffany’s and In Cold Blood, was a frequent visitor to Key West. While not a full-time resident, Capote’s visits to the island—often spent mingling with other literary greats—cemented his connection to Key West’s vibrant creative community.
Robert Frost: The Poet Laureate
Robert Frost, one of America’s most celebrated poets, spent winters in Key West during the 1940s. Frost stayed at a cottage behind the home of local residents Jessie and Jeanie Porter, which is now part of the Heritage House Museum. Frost’s connection to the island is commemorated through poetry readings and events held in his honor.
Other Notable Residents
Key West has also been home to a host of other fascinating figures, including:
Elizabeth Bishop: The Pulitzer Prize-winning poet found inspiration in Key West’s beauty and charm.
John James Audubon: While not a resident, Audubon’s visits to Key West inspired some of his most famous bird illustrations. The Audubon House and Tropical Gardens celebrate his legacy.
Howard Livingston: A local musician and former Chicago executive, Livingston’s music embodies the carefree spirit of Key West.
Why Key West Attracts the Famous
Key West’s unique allure lies in its combination of natural beauty, cultural richness, and welcoming community. The island’s laid-back atmosphere allows celebrities and creatives to escape the spotlight and embrace a simpler, more relaxed way of life. From its stunning sunsets to its vibrant arts scene, Key West continues to inspire and attract people from all walks of life.
From literary giants like Ernest Hemingway and Tennessee Williams to music legends like Jimmy Buffett and Kenny Chesney, the roster of famous Key West residents is as diverse as the island itself. Whether you’re exploring the Hemingway Home, visiting the Mel Fisher Maritime Museum, or simply soaking up the island’s bohemian vibe, Key West offers a glimpse into the lives of the remarkable individuals who have called it home. For those dreaming of paradise, Key West’s history and its famous residents prove that this tropical haven truly is a place where creativity and inspiration thrive.
