Sail into History: Private Sunset Sails Aboard a 1939 Schooner in Key West
Difficulty
easy
Duration
2 hours
Fitness Level
No special fitness required; suitable for all ages comfortable standing and light movement on deck.
Overview
Discover the magic of Key West’s waters on a private sunset sail aboard When And If, a 1939 wooden schooner with a fascinating past as General Patton’s own yacht. Experience history, hands-on sailing, and stunning scenery all in one unforgettable evening.
Private Sunset Sail When And If
Private Charter Sunset Sail on Classic Schooner Yacht
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Adventure Photos
About This Adventure
Embark on a memorable two-hour sailing adventure aboard a stunning 1939 wooden schooner yacht, once owned by General George S. Patton. Experience the thrill of raising sails, steering the helm, or simply relaxing while enjoying boutique beverages. Create your perfect journey on this unique piece of American maritime history.
Sail away on the gorgeous 1939 wooden schooner yacht built for General George S. Patton
Duration
2 hours
"When the war is over, and if I live through it, Bea and I are going to sail her around the world." When And If is the peacetime dream of an American war hero with her greatest destiny as yet unfulfilled. Come be part of the story of this gorgeous vessel as you help raise sail, take a turn at the helm or simply relax and enjoy this unique and timeless experience. Set sail on a beautiful piece of American history and enjoy the true blue-water sailing we offer on the Atlantic coast out of the lovely brand new Stock Island Marina.
What's Included
- Private use of the vessel with her captain and crew
- Boutique Wine, Beer and 4 bottles of Champagne
- Bottled water and seltzer water
Please Bring
- Appropriate weatherwear for the day
- Adequate sun protection
- Any snacks you'd like to enjoy during your trip
Private charter optional extras The beauty of private sailing is that the trip is yours to shape into your perfect sail. We can arrange:
- Extra time sailing
- Specific pick-up / drop-off locations
- Catering
Please don't hesitate to call us with any ideas and requests you may have - we'll do everything we can to make your dream sail come true!
Adventure Tips
Arrive Early to Relax
Get to the dock at least 15 minutes before departure to settle in and soak up the harbor views.
Sun Protection Is Key
Bring sunglasses and sunscreen to protect against the strong Florida sun, even in the evening.
Dress in Layers
Temperatures can drop after sunset; a light jacket or windbreaker keeps you comfortable.
Stay Hydrated
Even on cooler evenings, water is essential—especially if you plan to enjoy the boutique beverages.
Local Insights
Wildlife
- Bottlenose dolphins often play near the schooner’s path at sunset.
- Brown pelicans soar low over the Gulf’s surface, perfect for bird watchers.
History
The When And If schooner was famously owned by General George S. Patton, reflecting a unique piece of 20th-century American naval history.
Conservation
The crew practices sustainable boating methods, minimizing disturbance to marine life and preserving the waters around Key West.
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Adventure Hotspots in Key West
Frequently Asked Questions
Recommended Gear
Sunglasses
Protects eyes from glare off the water during sunset sails.
summer specific
Light Jacket
Keeps you warm as evening temperatures cool down on the water.
fall specific
Non-Slip Shoes
Ensures safe footing on the wooden deck of the schooner.
Camera
Captures unforgettable sunset and seascape moments.