Key West , Florida
Free CancellationFrom $ 40.00
Duration: 1 hours (approx.)Discover why Key West is one of the most haunted locations in the country on this 90 minute walking tour that starts at the corner of Duval and Caroline Streets, and led by your experienced guide and storyteller.
Key West , Florida
Free CancellationFrom $ 45.10
Duration: 1 hours (approx.)Experience the best of Key West on the famous Conch Tour Train! One of Florida’s most popular attractions, the Conch Tour Train has been entertaining visitors to the ‘Island City’ for decades. Learn about the history of the train, a tribute to Henry Flagler's engineering miracle when he brought the railroad to Key West in 1912, and explore this charming tropical paradise on a leisurely train ride around the island! FREE Admission to the Sails to Rails Museum included with ticket!
Key West , Florida
Likely to Sell Out Free CancellationFrom $ 46.99
Duration: 1 hours (approx.)Experience Historic Key West With A Small-Group Walking Tour Ever wondered how the island of Key West was discovered and became so rich? Explore Key West’s history, lore, and legends from the ground up with an intimate walking tour. Whether you want to learn more about the island’s first industries such as shipwrecking and cigarmaking, are curious about local history, or are looking for a fun-filled walk, Key West’s Historic Districts are waiting for you! This small-group walking tour offers both an educational experience and unparalleled delight for the lovers of history and culture. Our experienced local tour guides will lead you on an impressive stroll through the scenic streets of the Old Town where you can connect with the culture of a historic city. This unique experience is enjoyed by visitors from across the world and is a must-do while in Key West! What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
Key West , Florida
Free CancellationFrom $ 39.99
Duration: 1 hours (approx.)Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience and discovery, not just monuments and museums. You want to understand what’s behind the touristic façade that most people never penetrate. That’s why the Southernmost Walking Tour is the best way to immerse you into the history and culture of Key West! When you’re on foot, the world can’t slide past you faster than you can absorb it. You’ll have time – and proximity – to get up close to the region’s culture and natural history. Start your tour at the famous Cuban sandal factory - Kino Sandals before heading off toward the Southernmost Point of the continental United States. Along the way, our incredibly knowledgeable and well-connected local guides will show you the most popular landmarks and introduce you to local culture. By the time you’re finished, you’ll have a uniquely fun perspective of our tiny island!
Key West , Florida
Free CancellationFrom $ 59.99
Duration: 1 hours (approx.)Go beyond all of the Bars and drunk people to learn the “WHY” on how Key West became the home to many counter culture icons! Papa Hemingway, Jimmy Buffett, Tennessee Williams and more! This is Key West’s ONLY guided Art History Tour!!
Key West , Florida
Free CancellationFrom $ 35.00
Duration: 2 hours (approx.)Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for upcoming events, digital download of local artists music, and historical overviews of the venues and artists who have left their mark on the island. Learn from a local about the diverse music scene and creative island life that continues to inspire so many.
Key West , Florida
Free CancellationFrom $ 9.75
You may have heard the island of Key West called many different things – America’s Caribbean Island, Margaritaville or The Conch Republic. But you know what we locals call it? Paradise!! And I bet by the end of our tour you will agree with me. Go at your own pace. This is a smartphone guided tour that uses GPS to direct you step by step on a hands free adventure.
Key West , Florida
Free CancellationFrom $ 39.99
Duration: 96 hours (approx.)Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering hidden gems and local lore along the way . Explore the vast wetlands of Everglades National Park, encountering unique wildlife and ecosystems . Delve into the rich history and biodiversity of Big Cypress National Preserve . Finally, discover the underwater wonders of Biscayne National Park, from coral reefs to mangrove forests . With GPS-triggered narration, offline maps, and expert storytelling, enjoy the freedom to explore at your own pace without the constraints of group tours. Join thousands of travelers who have transformed their Florida road trips into enriching experiences—download now and let the Sunshine State's natural beauty and history captivate you!
Key West , Florida
Free CancellationFrom $ 11.99
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.
Cultural tours in Key West are the perfect way to explore the heart and soul of this remarkable destination. Unlike standard sightseeing, cultural tours allow you to immerse yourself in the traditions, stories, and daily life that make Key West truly unique. These experiences often include visits to historic landmarks, vibrant neighborhoods, bustling local markets, and cultural centers where the city’s rich heritage comes alive. Travelers can expect authentic encounters such as tasting regional dishes prepared with age-old recipes, joining guided walks that highlight architectural gems, or taking part in workshops that showcase local art and crafts. Beyond just seeing the sights, cultural tours create meaningful opportunities to connect with the people of Key West and better understand their history and way of life. Whether you are a solo traveler, part of a group, or exploring with family, these tours are designed to be both educational and memorable. They reveal layers of culture that ordinary trips often overlook. By joining a cultural tour in Key West, you not only witness its past and present but also become part of its ongoing story—carrying home lasting memories and deeper appreciation of the destination.
Our cultural tours in Key West are carefully curated to provide authentic experiences led by knowledgeable local guides. Each tour is designed to highlight the traditions, history, and unique stories that make Key West special, ensuring you leave with a deeper connection to the destination.