Overview

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.

Description

Pass By: Mallory Square, 400 Wall St, Florida 33040

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.

Pass By: Key West Historic Memorial Sculpture Garden, 401 Wall St, Florida 33040

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.

Pass By: Capt. Tony's Saloon, 428 Greene St, Florida 33040

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.

Pass By: Sloppy Joe's, 201 Duval St, Key West, FL 33040, USA

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.

Pass By: Caroline Street, Caroline St, Key West, FL 33040, USA

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.

Pass By: Harry S. Truman Little White House, 111 Front St, Florida 33040

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.

Pass By: The Marker Key West, 200 William St, Key West, FL 33040, USA

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.

Pass By: Duval Street, Duval Street, Florida 33040

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.

Pass By: San Carlos Institute, 516 Duval St, Florida 33040

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.

Pass By: The Hemingway Home and Museum, 907 Whitehead St, Key West, FL 33040, USA

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.

Pass By: Key West Lighthouse, 938 Whitehead St, Key West, FL 33040, USA

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.

Pass By: Southernmost Point of the Continental U.S.A., 1400 Whitehead St, Key West, FL 33040, USA

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