Key West Cruises, Sailing & Water Tours

Key West Schooner Backcountry Eco-Tour

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

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

5 hours (approx.) Free Cancellation
4.9 (216)
from
$110
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 …More

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
4.9 (681)
from
$150
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 …More

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
4.7 (220)
from
$197
Key West Dolphin Watch & Snorkel with FREE shuttle to location

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

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
4.9 (25)
from
$99
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 …More

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
4.5 (219)
from
$90
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
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
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

Likely to Sell Out
Likely to Sell Out

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
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 …More

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
4.9 (738)
from
$89
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 …More

Likely to Sell Out
Likely to Sell Out

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
4.8 (438)
from
$109
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 …More

Likely to Sell Out
Likely to Sell Out

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
4.9 (425)
from
$161
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 …More

Likely to Sell Out
Likely to Sell Out

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
4.8 (188)
from
$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 …More

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
5.0 (292)
from
$102
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and …More

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and...

4 hours Free Cancellation
4.9 (576)
from
$150
Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks …More

Likely to Sell Out
Likely to Sell Out

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks...

2 hours Free Cancellation
5.0 (22)
from
$102
Adult Only Sandbar Escape with Drinks in Key West

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being …More

Likely to Sell Out
Likely to Sell Out

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being...

4 hours Free Cancellation
4.8 (48)
from
$137
Key West Private Wind & Wine Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on City Balloon Tours three years running. See the sunset …More

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on City Balloon Tours three years running. See the sunset...

2 hours (approx.) Free Cancellation
5.0 (1,717)
from
$3,499
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 …More

Likely to Sell Out
Likely to Sell Out

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
4.9 (282)
from
$109
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 …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 (369)
from
$99
Sandbar Adventure Cruise in the Florida Keys

Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your …More

Likely to Sell Out
Likely to Sell Out

Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your...

4 hours Free Cancellation
4.9 (16)
from
$102
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 (182)
from
$65

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