• Audubon House & Tropical Gardens - Enter a charming 19th-century residence adorned with period decor, surrounded by vibrant tropical gardens teeming with native birds and meticulous landscaping. This serene haven offers insight into Key West’s sophisticated side and artistic heritage.
• Bahama Village - This lively historic district showcases the island’s rich Bahamian heritage through its colorful homes, Caribbean influences, and strong community spirit. Strolling here unveils a side of Key West shaped by hardworking families, faith, and culture.
• Conch Train Tour - A quintessential Key West attraction, this open-air train has been transporting visitors through the Old Town for years. Its cheerful presence highlights how the island has turned local storytelling into a shared visitor experience.
• Duval Street - The island’s most renowned street is alive with music, vibrant shops, historic bars, and shaded nooks. Spanning from the Gulf to the Atlantic, it embodies the lively rhythm that defines Key West life.
• The Ernest Hemingway Home and Museum - Nestled behind a high coral wall, this elegant Spanish Colonial home is where Ernest Hemingway penned some of his most famous works. The tranquil gardens and legendary six-toed cats make this a stop full of quiet inspiration and literary history.
• Green Parrot Bar - Once a neighborhood grocery, this relaxed bar has become a cherished gathering place for locals and wandering storytellers. Its unpretentious atmosphere reflects the island’s long-standing tradition of conversation, music, and community.
• Truman Little White House - This humble residence served as President Harry S. Truman’s winter retreat and working office. It remains today as a fascinating link between small-town Key West and world-shaping decisions.
• Key West Cemetery - Situated above sea level, this historic cemetery narrates the tales of storms, shipwrecks, epidemics, and vibrant island lives. Humorous and heartfelt epitaphs provide a surprisingly personal glimpse into the island’s past.
• Key West Historic Memorial Sculpture Garden - Nestled beside the waterfront, this tranquil garden honors writers, pioneers, and leaders connected to the island. Its statues create a reflective space where Key West’s layered history feels close at hand.
• Key West Lighthouse and Keeper’s Quarters Museum - Ascend to the top of this historic lighthouse for panoramic views over Old Town. Inside, the restored keeper’s home reveals the daily life of those who once guided ships through perilous coastal waters.
• Mallory Square - This renowned waterfront plaza is where Key West’s sunset celebration comes alive each evening with performers, artists, and ocean views. By day, it’s a relaxed gathering place that captures the island’s playful public spirit.
• The Oldest House Museum & Garden - Constructed in the early 1800s, this restored Conch-style home offers a rare glimpse into domestic life in Key West’s earliest years. Its tropical gardens and shaded porches preserve the quiet charm of frontier island living.
• Sloppy Joe’s - Made famous by Ernest Hemingway, this legendary bar has been a lively crossroads for sailors, writers, and travelers for nearly a century. Its bustling energy and historic character make it one of Duval Street’s most iconic stops.
• The Mansion On The Sea - With its distinctive coral-pink exterior, this grand 19th-century mansion stands just steps from the Atlantic. It reflects the wealth and ambition that once flowed through Key West during its maritime heyday.
• The Historic Armory - Originally constructed for military drills and civic events, this robust structure speaks to Key West’s strategic coastal role. Today, it stands as a reminder of the island’s blend of defense, community, and adaptation.
• Tennessee Williams Museum - This intimate museum celebrates the playwright’s years of work and reflection on the island. Through artifacts and film, it reveals how Key West shaped his creative voice and personal freedom.
• The Studios of Key West - Located in the former island armory, this vibrant arts center showcases rotating exhibitions, performances, and workshops. It continues Key West’s long tradition of supporting bold, independent artistic expression.
• Casa Marina Key West, Curio Collection by Hilton - This grand seaside resort opened in 1920 as one of the island’s first luxury destinations. Its expansive grounds and ocean views mark the moment Key West began redefining itself as a tropical retreat.
• Angela Street - A quiet, shaded lane named for a local woman of folklore, this street reveals Key West’s softer, more residential charm. Walking here offers a calm contrast to the energy of Duval Street, lined with cottages and island stories.

• Unlimited access
• Audio guide
• App and tour download

• Smartphone (bring your own)

Experience the lively essence of the Florida Keys with the Key West Conch and Hemingway Walk.

This self-paced journey immerses participants in the vibrant tapestry of island life, where renowned writers like Ernest Hemingway and Tennessee Williams found inspiration.

Wander through picturesque streets, bustling bars, and historic neighborhoods that highlight the distinctive fusion of Caribbean, Cuban, and Conch cultures.

As you explore at your leisure, captivating audio stories share tales of resilience, creativity, and community that define this legendary island.

Uncover the heart of Key West, where every corner invites reflection and connection with its rich history.

• Works entirely offline once downloaded—no cell service required
• GPS-triggered audio plays automatically based on your location
• Flexible - Buy once, use any day/time—access never expires
• Get the Drives & Detours app download the tour ahead of time

For a full refund, cancel at least 24 hours before the scheduled departure time.