• Mallory Square - Begin your journey in Mallory Square, the vibrant cultural center of Key West, where you can immerse yourself in the nightly Sunset Celebration and enjoy the lively atmosphere with street performers and breathtaking views.
• Key West Historic Memorial Sculpture Garden - Explore the Key West Historic Memorial Sculpture Garden, a serene oasis honoring the island’s rich history and notable figures, providing a peaceful retreat amidst the bustling city streets.
• Capt. Tony’s Saloon - Step into Capt Tony’s Saloon, a legendary watering hole steeped in history and character, where you can savor the island’s laid-back vibe and indulge in refreshing libations.
• Sloppy Joe’s - Experience the iconic Sloppy Joe’s Bar, a beloved Key West institution famous for its lively ambiance, live music, and signature cocktails, offering a taste of the island’s vibrant nightlife scene.
• Caroline Street - Wander down Caroline Street, one of Key West’s oldest thoroughfares, lined with charming shops, galleries, and eateries, where you can soak in the island’s unique charm and vibrant culture.
• Truman Little White House - Visit the Truman Little White House, a historic landmark where President Harry Truman sought refuge and relaxation, providing insight into the island’s presidential connections and political history.
• The Marker Key West - Pause at the Mile Zero Marker, the symbolic beginning of US Route 1, and capture a memorable photo to commemorate your journey through Key West and the start of your island adventure.
• Duval Street - Explore Duval Street, Key West’s vibrant main thoroughfare, lined with eclectic shops, bustling cafes, and historic landmarks, where you can soak up the island’s eclectic energy and vibrant street life.
• San Carlos Institute - Discover the San Carlos Institute, a historic cultural center celebrating Cuban heritage and fostering artistic expression, serving as a testament to Key West’s diverse cultural influences.
• The Hemingway Home and Museum - Step into The Hemingway Home and Museum, the former residence of renowned author Ernest Hemingway, where you can explore the iconic property and learn about the writer’s life and legacy on the island.
• Key West Lighthouse - Ascend the Key West Lighthouse, an iconic landmark offering panoramic views of the island and surrounding seascape, providing a glimpse into Key West’s maritime heritage and coastal charm.
• Southernmost Point of the Continental U.S.A. - End your journey at the Southernmost Point of the Continental USA, a symbolic marker commemorating the southernmost tip of the United States, offering stunning views and a memorable end to your Key West adventure

• Unlimited, lifetime use of the tour before and after booking date
• Virtual playback option to listen like an audiobook from anywhere
• Offline access to audio, maps, and geodata
• Self-guided GPS tour for exploring at your own pace
• Directions to the starting point for automatic tour start

Key West is famous as mainland America’s Caribbean resort town. Here, time slows down as the island vibes take over. But, as you’ll soon find out on this walking tour, there’s more to this island than umbrella drinks and warm breezes.

On this tour, travel writer and tour guide Gregg Squeglia will share stories of some of the island’s more famous residents and some lesser-known tales that have given Key West its unique place in American culture and history.

He’ll tell you about Key West’s incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships along the Great Florida Reef to the hilarious creation of the ‘Conch Republic’. You’ll also find out how, soon after its creation, this micro-state declared war on the United States for a full minute.

On this self-paced tour, you’ll also visit the island’s major landmarks and lesser-known treasures.

• Entrance fees to ticketed attractions are not included in the product’s total price

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