Top Key West Cruises, Sailing & Water Tours

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Key West Adventures

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Key West Sunset Cruise: Dinner, Live Music & Drinks Included
Likely to Sell Out
Likely to Sell Out
4.4 (1,863)

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.4 (1,863)
$92.95
$91.95
Key West Mangrove Kayak Eco Tour
Special Offer
Special Offer
4.9 (2,354)

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 (2,354)
$80
$79
Key West Signature Sunset Sail with Live Music, Open Bar & Food
Likely to Sell Out
Likely to Sell Out
4.7 (398)

Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (398)
$72
$71
Key West Dolphin and Snorkel Experience
Likely to Sell Out
Likely to Sell Out
4.7 (334)

Key West Dolphin and Snorkel Experience

The Top10Adventures® Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.7 (334)
$69.95
$68.95
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
Key West Reef Snorkel & Sail Adventure
Likely to Sell Out
Likely to Sell Out
4.8 (541)

Key West Reef Snorkel & Sail Adventure

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.8 (541)
$79
$78
Shark and Wildlife Viewing Adventure in Key West
Likely to Sell Out
Likely to Sell Out
5.0 (3,226)

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 (3,226)
$99
$98
Key West Reef Morning Snorkeling with Breakfast and Mimosas
Special Offer
Special Offer
4.7 (653)

Key West Reef Morning Snorkeling with Breakfast and Mimosas

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.7 (653)
$49.95
$48.95
Sunset Sail in Key West with Beverages Included
Likely to Sell Out
Likely to Sell Out
4.9 (962)

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 (962)
$79
$78
Key West Afternoon Reef Snorkeling with Open Bar
Likely to Sell Out
Likely to Sell Out
4.6 (437)

Key West Afternoon Reef Snorkeling with Open Bar

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.6 (437)
$59.95
$58.95
Key West Safari Eco Sandbar Tour Adventure with Snorkeling
Special Offer
Special Offer
4.7 (217)

Key West Safari Eco Sandbar Tour Adventure with Snorkeling

Explore Key West in a fun and unique way! Avoid the crowds on this exciting snorkel safari adventure and captain your own speedboat through 28...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.7 (217)
$197.12
$196.12
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Likely to Sell Out
Likely to Sell Out
4.9 (965)

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...

2 hours
2 hours
2 hours
4.9 (965)
$108.91
$107.91
All-Inclusive Sandbar Safari with Dolphin Playground Encounter
Special Offer
Special Offer
4.8 (606)

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 (606)
$149.95
$148.95
Guided Clear Kayak Eco-Tour Near Key West
Likely to Sell Out
Likely to Sell Out
4.9 (706)

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 (706)
$79
$78
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
Guided Night Kayak Adventure Tour in Luminous Lagoon
Likely to Sell Out
Likely to Sell Out
4.4 (185)

Guided Night Kayak Adventure Tour in Luminous Lagoon

Our Key West guided Night Kayak Tour is not just a journey through the water, but a night time nocturnal adventure! Our local guides will...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.4 (185)
$89.95
$88.95
Shallow Water Snorkeling and Dolphin Watching in Key West
Likely to Sell Out
Likely to Sell Out
4.8 (437)

Shallow Water Snorkeling and Dolphin Watching in Key West

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

4 hours
4 hours
4 hours
4.8 (437)
$108.91
$107.91
Key West Mini Catamaran Eco Tour
Likely to Sell Out
Likely to Sell Out
4.8 (174)

Key West Mini Catamaran Eco Tour

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (174)
$284.95
$283.95
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's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks
Likely to Sell Out
Likely to Sell Out
4.6 (33)

Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar &...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
4.6 (33)
$149.95
$148.95

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We guarantee the lowest price on all the adventures available to book on our site. We'll refund the difference if you find the exact adventure cheaper online until 48 hours before your adventure starts.

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