Top Key West Luxury Tours

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Key West Adventures

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Shark and Wildlife Viewing Adventure in Key West
Special Offer
Special Offer
5.0 (3,194)

Shark and Wildlife Viewing Adventure in Key West

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (3,194)
$99
$98
Guided Bike Tour of Old Town Key West
Special Offer
Special Offer
5.0 (2,684)

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (2,684)
$59
$58
Key West Mangrove Kayak Eco Tour
Special Offer
Special Offer
4.9 (2,350)

Key West Mangrove Kayak Eco Tour

Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (2,350)
$80
$79
Southernmost Food & Cultural Walking Tour by Key West Food Tours
Likely to Sell Out
Likely to Sell Out
4.9 (1,904)

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...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.9 (1,904)
$90.19
$89.19
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Likely to Sell Out
Likely to Sell Out
4.9 (1,701)

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (1,701)
$122.59
$121.59
Sunset Sail in Key West with Beverages Included
Likely to Sell Out
Likely to Sell Out
4.9 (959)

Sunset Sail in Key West with Beverages Included

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (959)
$79
$78
Guided Clear Kayak Eco-Tour Near Key West
Likely to Sell Out
Likely to Sell Out
4.9 (703)

Guided Clear Kayak Eco-Tour Near Key West

100% Clear Kayaks: Unlike traditional kayaks, ours are completely see-through. As you paddle, you'll have a front-row seat to the vibrant marine life beneath the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (703)
$79
$78
Key West Historic Seaport Food & Walking Tour
Likely to Sell Out
Likely to Sell Out
4.9 (677)

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...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.9 (677)
$93.41
$92.41
Key West Craft Cocktail Crawl
Likely to Sell Out
Likely to Sell Out
4.9 (600)

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...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.9 (600)
$93.68
$92.68
All-Inclusive Sandbar Safari with Dolphin Playground Encounter
Special Offer
Special Offer
4.8 (578)

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.8 (578)
$149.95
$148.95
Private Looe Key Snorkel from Big Pine Key
Special Offer
Special Offer
5.0 (440)

Private Looe Key Snorkel from Big Pine Key

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (440)
$599
$598
Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks
Special Offer
Special Offer
4.9 (385)

Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.9 (385)
$149.95
$148.95
Key West Sunset Sail Aboard Legendary Schooner Appledore
Special Offer
Special Offer
5.0 (360)

Key West Sunset Sail Aboard Legendary Schooner Appledore

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (360)
$89
$88
Jimmy Buffett Tour
Special Offer
Special Offer
4.8 (308)

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...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (308)
$79
$78
Key West Historic Old Town Food Tour with 5 Authentic Tastings
Likely to Sell Out
Likely to Sell Out
4.8 (304)

Key West Historic Old Town Food Tour with 5 Authentic Tastings

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (304)
$108
$107
Sunset Sail Cruise in Key West
Likely to Sell Out
Likely to Sell Out
5.0 (285)

Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (285)
$95
$94
Key West Historic Bahama Village & Hemingway Heritage
Special Offer
Special Offer
5.0 (261)

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...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (261)
$56.99
$55.99
Classic Key West Schooner Sunset Sail with Full Open Bar
Likely to Sell Out
Likely to Sell Out
5.0 (243)

Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (243)
$109
$108
Key West Day Sail on Schooner America 2.0 with 2 Drinks
Likely to Sell Out
Likely to Sell Out
5.0 (210)

Key West Day Sail on Schooner America 2.0 with 2 Drinks

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (210)
$79.45
$78.45
Southernmost Key West History and Culture Small-Group Walking Tour
Special Offer
Special Offer
5.0 (134)

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...

1 hour 45 minutes • Free Cancellation
1 hour 45 minutes • Free Cancellation
1 hour 45 minutes • Free Cancellation
5.0 (134)
$49.99
$48.99

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