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Key West Cruises, Sailing & Water Tours

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Key West Tours

Key West Wind & Wine Sunset Sail
Likely to Sell Out
Likely to Sell Out
5.0 (1,689)

Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Tours of Key West for over a decade. In our opinion, this is the...

2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
5.0 (1,689)
$109
$99
Miami to Key West Day Trip with Glass Bottom Boat Cruise
Likely to Sell Out
Likely to Sell Out
4.6 (3,219)

Miami to Key West Day Trip with Glass Bottom Boat Cruise

Sightsee along the famous Overseas Highway then take a Key West Glass-Bottom Boat Cruise when you tour Key West on this great Miami to Key...

6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
4.6 (3,219)
$159
$119
Key West Sail, Snorkel, Kayak with Sunset Option
Likely to Sell Out
Likely to Sell Out
4.9 (2,695)

Key West Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.) • Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,695)
$99
$90
Key West Backcountry Safari
Likely to Sell Out
Likely to Sell Out
4.9 (2,695)

Key West Backcountry Safari

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

4.5 or 6.5 hours (approx.) • Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,695)
$120
$99
Key West Sunset Dinner Cruise
Likely to Sell Out
Likely to Sell Out
4.4 (1,873)

Key West Sunset Dinner Cruise

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 (1,873)
from
$92.95
Key West Mangrove Kayak Eco Tour
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)
from
$80
Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar
4.8 (3,741)

Key West Sunset Sail with 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...

2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
4.8 (3,741)
Best Rate
$79.95
Sunset Sip & Sail
Likely to Sell Out
Likely to Sell Out
4.7 (403)

Sunset Sip & Sail

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 (403)
from
$72
Schooner Appledore Key West Premium Sunset Sail with Hors D’oeuvres and Full Bar
4.9 (1,701)

Schooner Appledore Key West Premium Sunset Sail with Hors D’oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...

2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
4.9 (1,701)
Best Rate
$99.95
Key West Sunset Harbor Cruise
Special Offer
Special Offer
4.9 (128)

Key West Sunset Harbor Cruise

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...

2 hours (approx.) • Hotel pickup offered • Free Cancellation
2 hours (approx.) • Hotel pickup offered • Free Cancellation
2 hours (approx.) • Hotel pickup offered • Free Cancellation
4.9 (128)
$99
$89
Key West Dolphin Watch Sunset Snorkel Cruise
Likely to Sell Out
Likely to Sell Out
4.7 (337)

Key West Dolphin Watch Sunset Snorkel Cruise

The Tours of Key West Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.7 (337)
from
$69.95
Key West Sunset Sail Aboard Schooner America 2.0
Likely to Sell Out
Likely to Sell Out
4.9 (1,701)

Key West Sunset Sail Aboard Schooner America 2.0

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)
from
$122.59
Key West Sunset Snorkel Sail
Likely to Sell Out
Likely to Sell Out
4.8 (191)

Key West Sunset Snorkel Sail

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.8 (191)
from
$69.95
Reef Snorkel & Sail Adventure – Afternoon
Likely to Sell Out
Likely to Sell Out
4.8 (541)

Reef Snorkel & Sail Adventure – Afternoon

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)
from
$79
Key West Shark and Wildlife Catamaran Tour
5.0 (3,237)

Key West Shark and Wildlife Catamaran Tour

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 (3,237)
from
$99
Famous Key West Sunset Sail
Likely to Sell Out
Likely to Sell Out
4.9 (963)

Famous Key West Sunset Sail

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 (963)
from
$79
Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak
4.9 (216)

Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...

5 hours (approx.) • Free Cancellation
5 hours (approx.) • Free Cancellation
5 hours (approx.) • Free Cancellation
4.9 (216)
Best Rate
$109.95
Champagne Celebration Sunset Cruise
Likely to Sell Out
Likely to Sell Out
4.9 (965)

Champagne Celebration Sunset Cruise

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)
from
$108.91
Key West Dolphin Watch & Snorkel
4.9 (25)

Key West Dolphin Watch & Snorkel

Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....

3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
4.9 (25)
Best Rate
$99
Key West Classic Day Sail Aboard America 2.0
Likely to Sell Out
Likely to Sell Out
5.0 (210)

Key West Classic Day Sail Aboard America 2.0

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)
from
$79.45

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