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Top Key West Cultural & Theme Tours

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Dolphin Research Center and Florida Keys Tour

Keep your eyes free to roam on this tour of the Lower Keys from Key West. Ride in a comfortable van across the Overseas Highway and more than 20 bridges en route to three islands, including stops at Bahia National Park, Blue Hole, and more. This small-group tour is limited to 13 passengers or fewer, and the driver is equipped with an audio headset to ensure you can hear while driving.
  • Duration: 6 hours 30 minutes
  • Free Cancellation
  • Duration: 6 hours 30 minutes
  • Free Cancellation
From  
$155.88 USD
From  
$155.88 USD
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Key West Ghost and Gravestone Tour

Discover some of Key West’s deepest, darkest secrets on a 90-minute ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of one of the most haunted cities in the country. Experience Key West’s frightening past while traveling down the narrow, dark streets of Old Town, lined with 19th-century wooden houses that still bear the secrets of their former inhabitants. This tour is narrated by a 17th-century gravedigger guide who’s almost as scary as the stories being shared.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$35.70 USD
From  
$35.70 USD
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Key West Pub Crawl

Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$34.99 USD
From  
$34.99 USD
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Key West Haunted Pub Crawl

Experience Key West’s dark side on this fun yet frightening haunted bar crawl. Hear tales of known paranormal activity from your local guide and visit the most eerie bars in Old Town Key West – located in two haunted mansions and repurposed morgue. By the end of the 2‐hour tour, you’ll see ‘Bone Island’ in a different (and profoundly spookier) light.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$19.89 USD
From  
$19.89 USD
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Snorkel and Sunset Sail: Rum n' Reggae

Combine a snorkel session on North America's only living coral reef with a Key West sunset during this 3-hour catamaran cruise. Listen to lively reggae beats, snorkel using the provided equipment, and watch the sunset with a rum punch in hand.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$48.32 USD
From  
$48.32 USD
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Key West Ghost Hunt

Discover some of Key West’s deepest, darkest secrets on a guided, 90-minute, ghost-themed walking tour. This small-group ‘frightseeing’ tour explores the darker side of one of the most haunted cities in the country. Experience the island’s frightening past while traveling down the narrow, dark streets of Old Town, lined with 19th-century wooden houses that still bear the secrets of their former inhabitants. Use of specialized ghost-hunting equipment included.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$30.00 USD
From  
$30.00 USD
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NEW TO VIATOR

Key West Ghost and Mysteries Tour

Discover the spooky side to one of the country's most haunted cities on a 90-minute walking tour. Listen to hair-raising local legends as you follow your guide down the hidden alley's of Key West. See where Robert the Doll lived, learn about Count Von Cosel, and keep your eyes peeled for the ghost at La Concha. Learn how to attract spirit activity with dowsing rods and how to capture it with your camera.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$29.15 USD
From  
$29.15 USD
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Old Town Literary Walking Tour

Explore the literary highlights of Key West during this walking tour, inspired by David A. Kaufelt’s original literary walking tour. An in-the-know guide whisks you around the Old Town to the former homes and favorite haunts of writers that have called the island home, including Shel Silverstein, Tennessee Williams, and Robert Frost. Since this is a small-group tour, you’ll have plenty of time to ask questions, too.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$30.00 USD
From  
$30.00 USD
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Key West Food, Drink and History Tour

Get to know the sights, sounds and tastes of Key West on this guided, 3-hour, small-group tour. Enjoy three drinks and three food tastings at some of the best pubs, dives and diners in Old Town and the Historic Seaport at Key West Bight Marina. Also, visit the Key West Legal Rum Distillery for a tour and tasting. Along the way, learn about the rich history and traditions of this island city, whose visitors have included fortune hunters, wreckers, spongers, pirates, tobacconists, artists, poets and writers.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
$89.00 USD
From  
$89.00 USD
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NEW TO VIATOR

Southernmost Historical Tour

Travel The Keys is a guided tour and concierge company based in Key West, Florida. We offer unique historical tours in Key West, presented by a 5th generation local. Our tours present a collection of lesser known historical events and explore the cultural legacies of the Southernmost District and surrounding areas of Key West.
  • Duration: 1 to 90 minutes
  • Free Cancellation
  • Duration: 1 to 90 minutes
  • Free Cancellation
From  
$30.00 USD
From  
$30.00 USD
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NEW TO VIATOR

Historic Old Town Private Walking Tour in Key West

There is so much more to Key West than food and pub crawls! While there is plenty of food and drink to be enjoyed, please don't let this be your only Key West experience. Join me, a multi-generational native Conch and learn about Key West's incredible history on this one-of-a-kind tour. I will help you bridge the gap between the vacation destination Key West is today, and the thriving island it once was for pirates, the military, treasure hunters, cigar rollers, entrepreneurs, and ordinary people with stories of the good, the bad, and the ugly Key West. If you miss this unique tour, you have missed Key West!
  • Duration: 1 to 2 hours
  • Free Cancellation
  • Duration: 1 to 2 hours
  • Free Cancellation
From  
$75.00 USD
From  
$75.00 USD
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NEW TO VIATOR

Bahama Village, Hemingway Museum, and Southernmost Point

We'll begin in old Key West where pirates first discovered the island. We'll stroll along the houses of ship captains and wreckers learning their history and will pause for a photo at Mile 0. We'll pass the historic Courthouse, a centuries old church, and enter Bahama Village and explore this culturally rich African-Caribbean neighborhood. We'll wind our way over to the home where Hemingway wrote many of his novels, stroll past the city's lighthouse, and end the tour at the Southernmost Point landmark.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$75.00 USD
From  
$75.00 USD
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Tour to Key West from Marathon

Visit the one-and-only island city of KEY WEST!Enjoy a narrated tour on the way down, and island music on the way back.HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Choose to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more!Sit back & enjoy the scenery as we drive down to Key West.Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide.See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory SquareIt's more like a road trip with friends than a tour - ask questions, point out wildlife, make new friends.
  • Duration: 7 hours
  • Free Cancellation
  • Duration: 7 hours
  • Free Cancellation
From  
$84.93 USD
From  
$84.93 USD
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(888) 651-9785
(888) 651-9785