Private Day Sail in Key West

Instant Booking
Family, Groups, Sailing, Coastal

Are you ready for a private day sail in Key West?

On this private day sail in Key West you can enjoy sailing away on the gorgeous 1939 wooden schooner yacht built for General George S. Patton. "When and If" is the story of an American combat hero and an amazing piece of American history. Come join the story of this beautiful ship as you assist in raising sail, take the helm for a while, or simply unwind and soak in this one-of-a-kind and enduring experience.

Enjoy the pure blue-water sailing along the Atlantic coast and the wonderful, new Stock Island Marina as you set sail on a stunning piece of American history. Private captain and crew, wine and selected beers, bottled water and seltzer water are included. Please bring appropriate clothig for the day, adequate sun protection, and any snacks you'd like to enjoy during your trip.

The beauty of private sailing is that the trip is yours to shape into your perfect sailing tour. Our friendly crew will set up meals, extra sailing time, particular pick-up and drop-off locations, and much more! Please don't hesitate to call or email us with any ideas and requests you may have; we'll do everything we can to make your dream come true!

What are you waiting for? Join us now for an unforgettable private day sail charter in Key West.



  • Enjoy the view over the amazing coastline from a unique perspective;

  • This experience will give you access exclusive areas far from the busy touristic areas;

  • Enjoy the art of sailing and the feel the power of the wind;


  • All sea experiences are subject to the weather and sea conditions. In case of bad conditions, we'll contact you to reschedule or arrange a refund;

  • Detailed tour operator information, including local phone number and exact address, is included in your confirmation email;

  • We recommend bringing sunscreen, swimming gear, a hat and a towel;

  • We recommend bringing your camera for the greatest pics of your holidays;


  • Let your private skipper take you to the most amazing secret spots in the area;

  • Perfect activity for your group of friends or family to celebrate special occasions;

  • A local captain will give you onboard commentary about the sights;

  • We'll serve some drinks and snacks and feel free to bring your own as well;

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Private Day Sail in Key West