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Top 10 Best Key West Sailing Trips

Found 47 Sailing Trips activities in Key West. Sort by Popularity.
 

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

(4.7 of 3,067 reviews)

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Free Cancellation
Start From $79.00
 
Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres Likely to Sell Out

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

  • Key West
  • Superb3,067 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Free Cancellation
    Start From $79.00
 
 

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

(4.9 of 648 reviews)

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 West, as you sail by Mallory Square, Sunset Pier, Sand K... More

Free Cancellation
Start From $116.10
 
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres Likely to Sell Out

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

  • Key West
  • Superb648 reviews4.9

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....

    Free Cancellation
    Start From $116.10
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 602 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Likely to Sell Out

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • Key West
  • Superb602 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

Sunset Sail in Key West with Beverages Included

(4.9 of 766 reviews)

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 to detail on our sunset cruise is legendary. Being out on the... More

Free Cancellation
Start From $79.00
 
Sunset Sail in Key West with Beverages Included Likely to Sell Out

Sunset Sail in Key West with Beverages Included

  • Key West
  • Superb766 reviews4.9

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....

    Free Cancellation
    Start From $79.00
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 89 reviews)

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 passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail Aboard Legendary Schooner Appledore Likely to Sell Out

Key West Sunset Sail Aboard Legendary Schooner Appledore

  • Key West
  • Superb89 reviews5

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Start From $89.00
 
 

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

(4.9 of 1,186 reviews)

Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for a romantic evening or just to enjoy time with friends. Please arrive 30 minutes prior to ... More

Free Cancellation
Start From $133.89
 
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres Likely to Sell Out

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

  • Key West
  • Superb1,186 reviews4.9

Cruise into the sunset with wines from all around the world, imported and domestic beers as well as ....

    Free Cancellation
    Start From $133.89
 
 

Key West Snorkeling with Breakfast and Unlimited Mimosas

(4.5 of 494 reviews)

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 Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Free Cancellation
Start From $46.94
 
Key West Snorkeling with Breakfast and Unlimited Mimosas Likely to Sell Out

Key West Snorkeling with Breakfast and Unlimited Mimosas

  • Key West
  • Exellent494 reviews4.5

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

    Free Cancellation
    Start From $46.94
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 501 reviews)

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 the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • Key West
  • Superb501 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Start From $79.00
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.8 of 44 reviews)

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More

Free Cancellation
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail Likely to Sell Out

Key West's Favorite Afternoon Dolphin Sail

  • Key West
  • Superb44 reviews4.8

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....

    Free Cancellation
    Start From $59.00
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 327 reviews)

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 West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Start From $54.95
 
Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

Key West Afternoon Reef Snorkeling with Open Bar

  • Key West
  • Exellent327 reviews4.5

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Start From $54.95
 
 

Sunset Sip and Sail Key West with Open Bar and Live Music

(4.5 of 255 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Start From $79.95
 
Sunset Sip and Sail Key West with Open Bar and Live Music Likely to Sell Out

Sunset Sip and Sail Key West with Open Bar and Live Music

  • Key West
  • Exellent255 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Free Cancellation
    Start From $79.95
 
 

Adults only Sunset Cruise from Key West with Champagne

(4.9 of 872 reviews)

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are the house champagne Chandon Brut, 7 premium red and whit... More

Free Cancellation
Start From $108.91
 
Adults only Sunset Cruise from Key West with Champagne Likely to Sell Out

Adults only Sunset Cruise from Key West with Champagne

  • Key West
  • Superb872 reviews4.9

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Ch....

    Free Cancellation
    Start From $108.91
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 262 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Free Cancellation
Start From $64.95
 
Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • Key West
  • Exellent262 reviews4.4

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Free Cancellation
    Start From $64.95
 
 

Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail

(4.4 of 346 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Free Cancellation
Start From $59.07
 
Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail

  • Key West
  • Exellent346 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Free Cancellation
    Start From $59.07
 
 

Sunset Sail Cruise in Key West

(4.9 of 211 reviews)

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 most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Start From $91.38
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • Key West
  • Superb211 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Start From $91.38
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 431 reviews)

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Free Cancellation
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • Key West
  • Superb431 reviews4.6

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....

    Free Cancellation
    Start From $108.91
 
 

Key West Sunset Snorkel with Unlimited Draft Beer & Wine

(4.7 of 114 reviews)

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 enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Free Cancellation
Start From $56.95
 
Key West Sunset Snorkel with Unlimited Draft Beer & Wine Likely to Sell Out

Key West Sunset Snorkel with Unlimited Draft Beer & Wine

  • Key West
  • Superb114 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Free Cancellation
    Start From $56.95
 
 

Sunset Sail on Historic Schooner in Key West

(4.8 of 95 reviews)

Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is over and if I return, Bea and I will sail around the world!" Step foot on the gorgeous teak... More

Free Cancellation
Start From $109.00
 
Sunset Sail on Historic Schooner in Key West Likely to Sell Out

Sunset Sail on Historic Schooner in Key West

  • Key West
  • Superb95 reviews4.8

Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then ....

    Free Cancellation
    Start From $109.00
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 125 reviews)

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 the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Start From $79.00
 
Key West Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • Key West
  • Superb125 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Start From $79.00
 
 

Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco

(5 of 149 reviews)

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and bein... More

Free Cancellation
Start From $156.00
 
Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco Likely to Sell Out

Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco

  • Key West
  • Superb149 reviews5

I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world w....

    Free Cancellation
    Start From $156.00
 
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