Key West Cruises, Sailing & Water Tours

96 Results
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 …More

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
4.7 (694)
from
$54
Schooner Appledore Day Sail with Full Bar in Key West

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 …More

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
5.0 (113)
from
$54
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 …More

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
4.6 (463)
from
$59
Key West Clear Kayak Eco Tour

Discover the natural beauty of Key West on our 2-Hour Guided Clear Kayak Eco Tour. Paddle through crystal-clear waters in a completely transparent bottom kayak, …More

Likely to Sell Out
Likely to Sell Out

Discover the natural beauty of Key West on our 2-Hour Guided Clear Kayak Eco Tour. Paddle through crystal-clear waters in a completely transparent bottom kayak,...

2 hours Free Cancellation
4.7 (50)
from
$60
Sharkeys Glass Bottom Fish Feeding LED Night Tour Key West

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point …More

Likely to Sell Out
Likely to Sell Out

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point...

1 hour 15 minutes Free Cancellation
5.0 (1)
from
$62
Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure …More

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure...

2 hours
4.9 (184)
from
$65
2 Hour Mangrove Maze Kayak Tour in Key West

Navigate through the stunning Mangrove Tunnels on this engaging 2-hour kayak tour in Key West. Ideal for all ages and skill levels, this adventure allows …More

Navigate through the stunning Mangrove Tunnels on this engaging 2-hour kayak tour in Key West. Ideal for all ages and skill levels, this adventure allows...

2 hours Free Cancellation
5.0 (9)
from
$65
Key West Dolphin and Snorkel Experience

The Key West Private ChartersDolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world …More

The Key West Private ChartersDolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world...

3 hours Free Cancellation
4.7 (345)
from
$70
Key West Glass Bottom Boat Reef Eco Tour with Sunset Option

The Key West Glass Bottom Boat Tour combines an entertaining, educational exploration of the reefs & marine life around Key West with a classic sunset …More

The Key West Glass Bottom Boat Tour combines an entertaining, educational exploration of the reefs & marine life around Key West with a classic sunset...

2 hours (approx.) Free Cancellation
4.6 (538)
from
$70
A Snorkel Tour with a Twist of History, Marathon, Florida Keys

Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat …More

Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat...

3 hours Free Cancellation
5.0 (1)
from
$70
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 • …More

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
4.6 (432)
from
$77
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 …More

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
4.8 (550)
from
$79
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 …More

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
4.9 (984)
from
$79
Key West Sunset Sail with Live Music, Champagne,  Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran …More

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

2 hours (approx.) Free Cancellation
4.8 (3,837)
from
$80
Key West "Commotion on the Ocean" Live Music Sunset Sail

This is the Key West sunset cruise party everyone talks about — live music, open-bar beer, wine, & margaritas, delicious appetizers, dancing, and a great …More

Likely to Sell Out
Likely to Sell Out

This is the Key West sunset cruise party everyone talks about — live music, open-bar beer, wine, & margaritas, delicious appetizers, dancing, and a great...

2 Hours (approx.) Free Cancellation
4.8 (996)
from
$80
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 …More

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
4.9 (2,390)
from
$80
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 …More

Likely to Sell Out
Likely to Sell Out

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
5.0 (213)
from
$82
Florida Keys Tiki Boat Tour Adventure

Embark on a lively 1.5-hour Tiki Fun Cruise through the stunning Florida Keys. Glide over crystal-clear waters on an authentic tiki bar boat, where you …More

Embark on a lively 1.5-hour Tiki Fun Cruise through the stunning Florida Keys. Glide over crystal-clear waters on an authentic tiki bar boat, where you...

2 hours Free Cancellation
5.0 (34)
from
$85
Dinghy Drinking Tour through Key West Waters

On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to …More

On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to...

3 hours Free Cancellation
4.9 (108)
from
$85
Florida Keys Sunset Cruise with Champagne Toast and Seafood

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing cruise includes a complimentary champagne toast and …More

Likely to Sell Out
Likely to Sell Out

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing cruise includes a complimentary champagne toast and...

2 hours Free Cancellation
5.0 (33)
from
$85
Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy …More

Likely to Sell Out
Likely to Sell Out

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy...

1 hour 45 minutes Free Cancellation
5.0 (5)
from
$89

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