Walking Tours in Key West
Top 10 Best Key West Walking Tours
Found 48 Walking Tours activities in Key West. Sort by Popularity.Southernmost Food & Cultural Walking Tour by Key West Food Tours
Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in historic old town, dining on typical Cuban dishes, local seafood, and of ... More
Jimmy Buffett Tour
You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at Margaritaville. Musician Jimmy Buffett arrived in Key West 50 years ago in 1971. This walking tour will t... More
Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt
Are you ready for some "spirited" fun? Join us on a spine tingling adventure through Bone Island. After receiving your souvenir T-Shirt you will embark on a 2 hour haunted walking tour of Old Town Key West. Along the way we will e... More
Key West Historic Seaport Food & Walking Tour
Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood options) cuban sandwich & key lime pie tastings. Sample classic ingredie... More
Fort East Martello Ghost Tour & VIP Robert the Doll Experience
Don't let the trolley take you for a ride. We're the only ghost tour in Key West where you'll walk the dark halls of historic Fort East Martello with authentic ghost-hunting equipment and meet Key West's infamous haunted doll, Rob... More
Key West Historic District Small-Group Walking Tour
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 ... More
Original Key West Pub Crawl: The Best Bars with Free T-Shirt
If you’re looking for the ultimate Key West experience, join the 'Duval Crawl' pub crawl! Key West is famous for its lively bars. Join the original Key West Pub Crawl established in 2002. The only pub crawl that includes five dr... More
Key West Historic Homes and Island History - Small Group Walking Tour
Historic Homes & Island History of Key West- 2020, 2021, 2022, and 2023 WINNER- "Best Key West History Tour" TripAdvisor ranked top 10 history tours in North America. Join our award-winning guides for a wonderful, fun, and info... More
Key West Craft Cocktail Crawl
Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and ... More
PRIVATE Welcome to Key West Walking Tour
Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. This is private tour is customizable, meaning you can request to adjust the me... More
Private Tour
Key West Walking Food Tour With Secret Food Tours
On our Secret Food Tour: Key West Old Town, we'll walk far from the tourist traps of Duval to show you the real city and its best food. You'll gain insight into how the diverse cultural influences of Key West have shaped the islan... More
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Private Tour
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Key West Ghost and Mysteries Guided Tour
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. Walk down hidden ... More
Private Tour
Hemingway Tour
You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony's Saloon outside front doors (428 Greene Street). You will then be taken to several of Ernest Hemingway's haunts around Old Town ... More
Private Tour
Hemingway Food and Walking Tour
This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, where he kept his boat the Pilar, the bookstore where his books were sold, ... More
Private Tour
Southernmost Key West History and Culture Small-Group Walking Tour
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 ... More
Private Tour
2-Hour Live Music Guided Tour in Key West
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 overview... More
Private Tour
Private Professional Vacation Photoshoot in Key West
Get ready for an unforgettable photographic journey through Key West most iconic destinations! We’ll guide you on a relaxed exploration of the island’s most photogenic landmarks, showcasing the best Key West has to offer. Alo... More
Private Tour
Highlights and Stories of Key West - Small Group Walking Tour
Key West Highlights and Stories- 2020, 2021, 2022, and 2023 WINNER "Best Key West Walking Tour". Join our award-winning guides for a wonderful, fun, and informative 2.5 hour walk through the historic streets of Old Town Key West.... More
Private Tour
Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!
We invite you to take an exclusive cocktail & food taste tour on the Waterfront in Downtown Key West! Our seasoned local guide will dive into the history of Old Fisherman’s Wharf & how it has transformed into Yacht Harbor! ... More
Private Tour
The Dark Side of Key West Ghost Tour
The Dark Side of Key West is our adult’s only option that focuses on Key West’s dark and salacious past. We will discuss pirates, Count Von Cosel, Robert the Doll, and The Hemingway House. We will tell you all about the grisly... More
Private Tour