Have you ever dreamed of walking where Hemingway once wrote, drank, and lived out his island years? In Key West, you can.
Ernest Hemingway, one of America’s greatest writers, called this island home in the 1930s. He wrote some of his most famous works here, surrounded by the rays of the sun, the fresh air, and the kind of characters only Key West could think of. Today, you can tour the places that shaped his life and legacy, from his tropical garden home to his favorite and popular bar stool, on a walk that blends literary history with the island atmosphere.
Be ready to be in awe as you wander through Hemingway’s Key West at your own pace—most stops here are just steps apart, from his lush home to the lively Sloppy Joe’s and the historic lighthouse. This self-guided tour brings his world to life year-round. And while Hemingway Days may have wrapped up for the summer, the island’s literary soul is always intact.
Ernest Hemingway’s personal typewriter used to draft some of his most iconic works. Courtesy of Annie LangHemingway Tour Highlights
1. Ernest Hemingway Home and Museum
Step into the Spanish colonial-style house where Hemingway lived in the 1930s. Tour the rooms, peek into his upstairs studio—where he wrote To Have and Have Not—and say hello to the six-toed cats that roam the grounds, descended from Hemingway’s own.
Located just off Duval Street, this legendary bar was Hemingway’s favorite haunt. It still hums with live music, cold drinks, and walls filled with photos and stories from his time. Order a daiquiri and imagine the conversations that once filled the air.
Just across from his home, the lighthouse offers the same sweeping views Hemingway once admired. Climb the 88 steps for a panoramic look at the island that inspired so much of his work.
This beautifully restored landmark houses rotating exhibits on Key West’s cultural history, including Hemingway’s legacy. It’s the perfect place to add depth and context to your tour.
5. Hemingway Days Festival (July)
If you’re visiting in the summer, this annual event celebrates Hemingway with look-alike contests, literary readings, and fishing tournaments. It’s a festive tribute to his lasting presence on the island. Next year’s festival is scheduled for July 22–26, 2026, in Key West, Florida. Don’t miss it!
Insider Tip: Recommended Readings
- The Old Man and the Sea (1952) – A quiet, powerful story of endurance at sea
- The Sun Also Rises (1926) – A postwar journey through Spain and longing
- For Whom the Bell Tolls (1940) – War, love, and sacrifice in the Spanish mountains
Ready to follow in Hemingway’s footsteps? Rentalz makes it easy to find a vacation rental just steps from the writer’s favorite spots. Stay close to the stories and the amazing experience on your Key West escape.
The Hemingway Tour is a rich, unforgettable way to experience Key West, immersing you in history, literature, and the island joys into one remarkable journey.
Pack your curiosity and a good book—Hemingway’s island is waiting!
