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Top 10 Best Key West Sailing Trips

Found 48 Sailing Trips activities in Key West. Sort by Popularity. - Page 3
 

Schooner Bloody Mary Day Sail with Full Open Bar in Key West

(4.9 of 9 reviews)

Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in paradise! While enjoying your sail remember there is plenty to see on the water’s surface or circling in the blue sky above you. P... More

Free Cancellation
Start From $49.00
 
Schooner Bloody Mary Day Sail with Full Open Bar in Key West

Schooner Bloody Mary Day Sail with Full Open Bar in Key West

  • Key West
  • Superb9 reviews4.9

Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in pa....

    Free Cancellation
    Start From $49.00
 
 

Private Sunset Sail in Key West Florida

(4.9 of 9 reviews)

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, l... More

Free Cancellation
Private Tour
Start From $750.00
 
Private Sunset Sail in Key West Florida

Private Sunset Sail in Key West Florida

  • Key West
  • Superb9 reviews4.9

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just ....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

2-hour Customizable Private Day Sail in Key West

(1 of 1 review)

This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon one of our historic schooners. This trip has a capacity of up to 26 people, and a selection of sodas, beer, and wine are included... More

Free Cancellation
Private Tour
Start From $2,100.00
 
2-hour Customizable Private Day Sail in Key West

2-hour Customizable Private Day Sail in Key West

  • Key West

This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon....

    Free Cancellation
    Private Tour
    Start From $2,100.00
 
 

Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats

(1 of 1 review)

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More

Free Cancellation
Private Tour
Start From $350.00
 
Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats

Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats

  • Key West

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water ....

    Free Cancellation
    Private Tour
    Start From $350.00
 
 

Private Afternoon Snorkel with Sunset Sail in Key West

(5 of 4 reviews)

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

Free Cancellation
Private Tour
Start From $995.00
 
Private Afternoon Snorkel with Sunset Sail in Key West

Private Afternoon Snorkel with Sunset Sail in Key West

  • Key West
  • Superb4 reviews5

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that sp....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

Key West Haunted Night Sail on Schooner America 2.0

(5 of 4 reviews)

Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under the Key West night sky. During this night boat ride, we'll cruise through the waters of Key West while listening to mysterious t... More

Free Cancellation
Private Tour
Start From $88.15
 
Key West Haunted Night Sail on Schooner America 2.0

Key West Haunted Night Sail on Schooner America 2.0

  • Key West
  • Superb4 reviews5

Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under....

    Free Cancellation
    Private Tour
    Start From $88.15
 
 

Private 2-Hour Wind and Wine Sunset Sail in Key West

(4.9 of 81 reviews)

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More

Free Cancellation
Private Tour
Start From $4,000.00
 
Private 2-Hour Wind and Wine Sunset Sail in Key West Likely to Sell Out

Private 2-Hour Wind and Wine Sunset Sail in Key West

  • Key West
  • Superb81 reviews4.9

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from ....

    Free Cancellation
    Private Tour
    Start From $4,000.00
 
 

Key West Wreckers Race Aboard Schooner America 2.0

(4.9 of 9 reviews)

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More

Free Cancellation
Private Tour
Start From $111.80
 
Key West Wreckers Race Aboard Schooner America 2.0 Likely to Sell Out

Key West Wreckers Race Aboard Schooner America 2.0

  • Key West
  • Superb9 reviews4.9

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....

    Free Cancellation
    Private Tour
    Start From $111.80
 
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