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.
Get more from your trip from St. Louis to Springfield on Interstate 55
Hear interesting stories and history as you drive from the audio guide
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This tour is on the easy-to-download VoiceMap app
What To Expect
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.
• Admission Ticket Free
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.
• Admission Ticket Free
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.
• Admission Ticket Free
Sloppy Joe’s Bar
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.
• Admission Ticket Free
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.
• Admission Ticket Free
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.
• Admission Ticket Free
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.
• Admission Ticket Free
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.
• Admission Ticket Free
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.
• Admission Ticket Free
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.
• Admission Ticket Free
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.
• Admission Ticket Free
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
• Admission Ticket Free
Highlight
Confirmation will be received at time of booking
Not wheelchair accessible
Service animals allowed
Near public transportation
Most travelers can participate
Entrance fees to ticketed attractions are not included in the product’s total price
This is a private tour/activity. Only your group will participate
Include
Directions to the starting point so that when you’re in the right place, the tour will start
Get unlimited, lifetime use of this tour, before your booking date and after it
The virtual playback option, so you can listen to this tour like an audiobook from anywhere
Flexibility to explore at your own pace with a self-guided GPS tour
Offline access to audio, maps, and geodata