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Top Key West Historical & Heritage Tours

48 Results
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 …More

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...

2 hours Free Cancellation
5.0 (2,702)
from
$59
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 …More

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...

1 hour 30 minutes Free Cancellation
4.8 (321)
from
$79
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 …More

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...

1 hour 30 minutes Free Cancellation
5.0 (262)
from
$60
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 …More

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...

1 hour 45 minutes Free Cancellation
5.0 (135)
from
$54
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, …More

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,...

2 hours Free Cancellation
4.8 (109)
from
$99
Self-Guided Driving Audio Tour in Florida Keys

Don't miss a thing as the GuideAlong Audio Driving Tour takes you on an incredible self-guided journey on one of the most classic US road …More

Don't miss a thing as the GuideAlong Audio Driving Tour takes you on an incredible self-guided journey on one of the most classic US road...

1 day Free Cancellation
4.8 (98)
from
$20
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 …More

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...

4 hours Free Cancellation
4.9 (73)
from
$189
Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs

You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting …More

You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting...

2 hours 30 minutes Free Cancellation
5.0 (69)
from
$158
Key Lime Pie Walking Tour of Key West Historic Seaport

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie, …More

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie,...

1 hour 30 minutes Free Cancellation
4.9 (62)
from
$70
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 …More

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...

7 hours Hotel pickup offered Free Cancellation
4.9 (37)
from
$100
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 …More

Likely to Sell Out
Likely to Sell Out

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...

90 to 180 minutes Free Cancellation
4.9 (22)
from
$55
Tropical Fruit Hunting Tour at Grimal Grove

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on …More

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on...

1 hour 30 minutes Free Cancellation
5.0 (21)
from
$41
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 …More

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...

1 hour 30 minutes Free Cancellation
4.8 (19)
from
$49
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the …More

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the...

2 hours Free Cancellation
5.0 (13)
from
$599
Key West: Robert the Doll After Dark Ghost Tour (1 Hour)

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most …More

Likely to Sell Out
Likely to Sell Out

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most...

1 hour Free Cancellation
4.9 (7)
from
$45
Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll …More

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll...

1 hour 30 minutes Free Cancellation
5.0 (7)
from
$158
History Nature and Culture of Key West Walking Tour

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local …More

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local...

1 hour 30 minutes Free Cancellation
5.0 (3)
from
$69
Key West Odyssey: Uncover Island Secrets, Walk by Locals

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic …More

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic...

1 hour 30 minutes Free Cancellation
5.0 (2)
from
$60
Key West UFO Skywatch Tour with Night Vision

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else …More

Likely to Sell Out
Likely to Sell Out

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else...

1 hour 15 minutes Free Cancellation
5.0 (1)
from
$49
Historic Key West Bike Tour

Explore the vibrant history of Key West on this engaging bike tour. Pedal through charming streets as you uncover the stories behind the island's notable …More

Explore the vibrant history of Key West on this engaging bike tour. Pedal through charming streets as you uncover the stories behind the island's notable...

2 hours Free Cancellation
5.0 (1)
from
$79

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