Embark on a historic schooner experience in Key West and set sail into the stunning sunset. Help raise the sail, take the wheel, or simply relax and enjoy the breathtaking views.
Embark on a historic schooner experience in Key West and set sail into the stunning sunset. Help raise the sail, take the wheel, or simply relax and enjoy the breathtaking views.
- Sunset Sail Key West - The vessel is moored at the Key West Historic Seaport, located at the end of E dock in front of the Waterfront Brewery. Look for the E sign on the dock piling and proceed to the end of the long pier. The schooner features varnished wooden masts with flags atop each mast. Check-in and boarding occur directly at the boat,…
- Sunset Sail Key West - The vessel is moored at the Key West Historic Seaport, located at the end of E dock in front of the Waterfront Brewery. Look for the E sign on the dock piling and proceed to the end of the long pier. The schooner features varnished wooden masts with flags atop each mast. Check-in and boarding occur directly at the boat, starting 15 minutes before departure.
- Florida Keys National Marine Sanctuary - Sailing through the National Marine Sanctuary provides a unique chance to observe marine wildlife, including sea turtles, bottlenose dolphins, and marine birds.
- Mallory Square - The sail passes by the renowned sunset celebration at Mallory Square.
- Opal Spa - Sunset Key - Enjoy a sail past the offshore Key West Island, home to the rich and famous, from the comfort of a seat aboard the majestic classic yacht.
- Carbonated beverages
- Bottled water
- Alcoholic beverages
- Experienced Captain and Crew
- On-board restrooms
- Opportunity to Take the Wheel and Help Raise Sail
- Carbonated beverages
- Bottled water
- Alcoholic beverages
- Experienced Captain and Crew
- On-board restrooms
- Opportunity to Take the Wheel and Help Raise Sail
- Gratuities
- Private transportation
- Ships Souvenirs Available for Purchase Onboard
- Gratuities
- Private transportation
- Ships Souvenirs Available for Purchase Onboard
Step onto the historic schooner, When And If, commissioned by General George Patton in the late 1930s, and embark on a stunning Key West sunset cruise. Toast with champagne as the sun sets on the horizon, while the skilled crew manages the sails — or take the opportunity to steer this classic wooden schooner yourself. Sail through turquoise waters,…
Step onto the historic schooner, When And If, commissioned by General George Patton in the late 1930s, and embark on a stunning Key West sunset cruise. Toast with champagne as the sun sets on the horizon, while the skilled crew manages the sails — or take the opportunity to steer this classic wooden schooner yourself. Sail through turquoise waters, observe playful dolphins and local wildlife, and enjoy an unforgettable evening that combines history, luxury, and adventure.
Highlights:
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Experience a historic schooner journey aboard the When And If, commissioned by General George Patton in 1939.
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Includes a champagne sunset toast
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Elegant and exclusive cruise - Avoid the crowds
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Hands-on sailing experience: steer the ship under the guidance of your experienced crew.
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Spot dolphins, sea birds, and local marine wildlife.
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Ideal for romantic evenings, family adventures, or history enthusiasts — children sail at a discounted rate.
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Children must be accompanied by an adult
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
