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Top 10 Best Key West Sailing Trips

Found 45 Sailing Trips activities in Key West. Sort by Popularity. - Page 3
 

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
 
 

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
 
 

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 Likely to Sell Out

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
 
 

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

(4.9 of 82 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
  • Superb82 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 Haunted Night Sail on Schooner America 2.0

(4.9 of 82 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 Likely to Sell Out

Key West Haunted Night Sail on Schooner America 2.0

  • Key West
  • Superb82 reviews4.9

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
 
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