Sail the Atlantic on a Historic 1939 Schooner in Key West
Difficulty
moderate
Duration
2 hours
Fitness Level
Basic physical fitness is sufficient, with some light movement on deck during sailing activities.
Overview
Step aboard the 'When And If,' a classic 1939 wooden schooner, for a private two-hour sailing adventure off the coast of Key West. Experience hands-on sailing or relax with stunning Atlantic views framed by historic charm.
Private Day sail on When And If
2 Hours • Classic Schooner Yacht Day Sailing
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Adventure Photos
About This Adventure
Embark on a memorable 2-hour sailing adventure aboard a stunning 1939 wooden schooner, once owned by General George S. Patton. Experience the thrill of raising sails, steering the helm, or simply relaxing while enjoying breathtaking views of the Atlantic coast. Customize your journey with private charters and catering options for a truly unique experience.
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
- Bottled water and seltzer water
- Wine $ select beers
*Beverage Upgrades Available
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
And much more! 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
Book Private Charters Early
Private charters fill quickly, especially during peak seasons; reserve ahead to guarantee your preferred date.
Bring Sun Protection
Wear sunscreen and a hat to guard against strong Florida sun while on deck.
Arrive Early for Check-In
Arriving 15 minutes early helps streamline boarding and allows time to settle in comfortably.
Wear Non-Slip Footwear
Closed-toe, non-slip shoes ensure safety on the wooden deck during sailing maneuvers.
Local Insights
Wildlife
- Dolphins commonly swim alongside the boat during trips.
- Brown pelicans often glide low over the water, providing great photo ops.
History
Key West's maritime history is rich with tales of shipwreck salvaging and naval significance dating back centuries.
Conservation
The operators follow eco-friendly sailing practices to minimize impact on delicate marine ecosystems in the Florida Keys National Marine Sanctuary.
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Adventure Hotspots in Key West
Frequently Asked Questions
Recommended Gear
Sunscreen
Protects skin from intense sun exposure over open water.
summer specific
Light Jacket
For cooler breezes on the water, particularly in early morning or late afternoon.
spring specific
Hat with Brim
Shields face and eyes from direct sunlight.
summer specific
Comfortable Non-Slip Shoes
Ensures safe footing on the schooner's wooden decks.