Historical & Heritage Tours in Key West
Top 10 Best Key West Historical & Heritage Tours
Found 55 Historical & Heritage Tours activities in Key West. Sort by Popularity.Guided Bike Tour of Old Town Key West
Ride with Key Lime Bike Tours for a truly unique and unforgettable Key West experience! See the islands top attractions with your own friendly knowledgable guide! Cruise Old Town, visit iconic landmarks, and hear stories about som... More
Guided Bike Tour of Old Town Key West
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Key West
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Superb2,613 reviews4.9
Ride with Key Lime Bike Tours for a truly unique and unforgettable Key West experience! See the isla....
Key West Conch Tour Train
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 ... More
Key West Conch Tour Train
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Key West
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Exellent792 reviews4.4
Experience the best of Key West on the famous Conch Tour Train! One of Florida’s most popular attr....
The Hemingway Experience in Key West
The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour of Old Town. Our 4-hour guided experience stops at... More
Likely to Sell Out The Hemingway Experience in Key West
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Key West
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Superb31 reviews4.7
The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, ....
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
Likely to Sell Out Jimmy Buffett Tour
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Key West
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Superb291 reviews4.6
You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearin....
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
Likely to Sell Out Hemingway Food and Walking Tour
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Key West
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Superb105 reviews4.7
This guided walking tour will take you to the real places that Hemingway lived, worked and played, i....
Likely to Sell Out
VIP Robert the Doll After Dark
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
Free Cancellation
(Saving 20% )
Likely to Sell Out VIP Robert the Doll After Dark
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Key West
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Superb155 reviews4.7
Don't let the trolley take you for a ride. We're the only ghost tour in Key West where you'll walk t....
Free Cancellation
(Saving 20% )
Harry S Truman Little White House Admission
Tour the historic Harry S. Truman Little White House in Key West and learn about a fascinating period of American history. What was once a private compound on a U.S. Navy base is today open to the public as a museum. Listen to fas... More
Likely to Sell Out Harry S Truman Little White House Admission
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Key West
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Superb451 reviews4.7
Tour the historic Harry S. Truman Little White House in Key West and learn about a fascinating perio....
Key West Shore Excursion: Conch Tour Train
When you arrive in port in Key West, take a Conch Tour Train shore excursion on your own; you’ll see the best of Key West on the tour that's been entertaining visitors to the Island City since 1958. You’ll hear legends and lor... More
Likely to Sell Out Key West Shore Excursion: Conch Tour Train
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Key West
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Exellent34 reviews4.5
When you arrive in port in Key West, take a Conch Tour Train shore excursion on your own; you’ll s....
Key West Historic Bahama Village & Hemingway Heritage
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
Likely to Sell Out Key West Historic Bahama Village & Hemingway Heritage
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Key West
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Superb252 reviews5
Experience Historic Key West With A Small-Group Walking Tour Ever wondered how the island of Key We....
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! You'll travel halfway up the keys to Marathon and stop along the way to explore the natural splendor and man-made wonders of the Fl... More
Likely to Sell Out Full-Day Tour of Florida Keys Including Aquarium Encounters from ....
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Key West
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Superb30 reviews4.9
Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! Y....
iWitness Key West True Crime Walking Tour
True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and shocking history exposed where it happened. More thrilling th... More
Likely to Sell Out iWitness Key West True Crime Walking Tour
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Key West
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Superb8 reviews5
True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into th....
Hemingway's Key West Self Guided outdoor Walking Audio Tour
Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway house) See the many sites he's linked to? Stop in his favorite bars for a drink? You are in luck. Our tour will begin at the Florida... More
Private Tour
Likely to Sell Out Hemingway's Key West Self Guided outdoor Walking Audio Tour
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Key West
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Very Good1 review4
Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway ho....
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
Likely to Sell Out Hemingway Tour
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Key West
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Exellent13 reviews4.1
You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony....
Private Tour
The Ghosts of Key West Walking Tour
Get ready for a fun and fright-filled evening as we explore the haunted history of Key West! Starting at the charming River Street Sweets, we’ll stroll beneath the moonlight to some of the island’s most legendary landmarks. He... More
Private Tour
Likely to Sell Out The Ghosts of Key West Walking Tour
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Key West
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Exellent132 reviews4.3
Get ready for a fun and fright-filled evening as we explore the haunted history of Key West! Startin....
Private Tour
Old Town Key West Literary Walking Tour
Join us every weekend for the Old Town Literary Walking Tour, a stroll through downtown Key West, illuminating stories of writers that have called our island home. Inspired by David A. Kaufelt’s original literary walking tour, ... More
Private Tour
Likely to Sell Out Old Town Key West Literary Walking Tour
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Key West
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Superb101 reviews4.9
Join us every weekend for the Old Town Literary Walking Tour, a stroll through downtown Key West, i....
Private Tour
Key West Shipwreck Treasure Museum Admission
Learn about an important part of Florida’s history at the Key West Shipwreck Treasure Museum. Explore the wreckage of Spanish galleons and the remnants of cargo ships. Go back in time to the 19th century, when excavating shipwre... More
Private Tour
Likely to Sell Out Key West Shipwreck Treasure Museum Admission
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Key West
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Very Good100 reviews3.8
Learn about an important part of Florida’s history at the Key West Shipwreck Treasure Museum. Expl....
Private Tour
Likely to Sell Out
Key West’s Old Town Treasures: A Self-Guided Audio Tour
See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour. • Find out how the town nearly went bankrupt before reinventing itself as ‘The Conch Republic... More
Free Cancellation
Private Tour
(Saving 25% )
Likely to Sell Out Key West’s Old Town Treasures: A Self-Guided Audio Tour
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Key West
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Exellent29 reviews4.3
See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with....
Free Cancellation
Private Tour
(Saving 25% )
Sails to Rails Museum Admission
Located in the historic Key West Bight, discover this state-of-the-art museum with hands-on exhibits, raw footage, unique artifacts, and the only scale model of Fort Jefferson at Dry Tortugas National Park. As you travel through ... More
Private Tour
Likely to Sell Out Sails to Rails Museum Admission
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Key West
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Superb10 reviews4.7
Located in the historic Key West Bight, discover this state-of-the-art museum with hands-on exhibits....
Private Tour
Key West Conch and Hemingway Self-Guided Walk
Explore the vibrant spirit of the Florida Keys with the Key West Conch and Hemingway Walk. This self-guided adventure immerses you in the rich tapestry of island life where writers like Ernest Hemingway and Tennessee Williams fo... More
Private Tour
Likely to Sell Out Key West Conch and Hemingway Self-Guided Walk
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Key West
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Superb10 reviews4.7
Explore the vibrant spirit of the Florida Keys with the Key West Conch and Hemingway Walk. This se....
Private Tour
Key West Pirate Exploration Game and Tour
Uncover the secrets of Key West through a thrilling pirate-themed adventure! Step into the shoes of a clever detective on a sun-soaked island full of hidden clues, local legends, and centuries-old mysteries. Follow a trail of ri... More
Private Tour
Likely to Sell Out Key West Pirate Exploration Game and Tour
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Key West
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Superb10 reviews4.7
Uncover the secrets of Key West through a thrilling pirate-themed adventure! Step into the shoes of ....
Private Tour