Sunset Sailing Tour in Key West

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Family, Groups, Sunset, Coastal, Romantic, Sailing

Are you ready for a sunset sailing tour in Key West?

This sunset sailing tour in Key West will take you to enjoy a mesmerizing sunset on a gorgeous classic yacht. Come and have fun as we sail into the sunset, enjoying the unspoiled view and blue water sailing to be had off the Keys' Atlantic coast. 

This tour takes place on the sailboat "When and If," which was the peacetime dream of an American war hero, and at 82 years old, she is open to the public as part of a fund-raising program to preserve her flag, keep her in her current excellent condition, and fulfill her destiny to sail around the world. As our captain and crew sail you out to catch the breeze, you can help raise the sails, take a turn at the helm, or just unwind and enjoy the trip.

This trip includes seats on a shared experience on the schooner, a captain and crew, two boutique wines made in honor of the boat, selected beers, bottled water, and La Croix.

What are you waiting for? Join us now on this sunset sailing tour in Key West.



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

  • The perfect way to end a day with your family or group of friends;

  • The highlight of this stunning sunset cruise will surely be the magical touch of the colors of the sunset;

  • 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 and comfortable clothes;

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


  • 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;

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Sunset Sailing Tour in Key West