A Sailing Experience Like No Other

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The smell of salt water fills your lungs. A warm wind blows from behind, pushing the vessel forward. Waves crash in a calming rhythm. The bright light of the sun starts to develop a warmer orange hue as the clouds on the horizon gain pink and lilac tones. Sailing across the 90 miles that stand between Key West and Cuba’s Hemingway Marina aboard of When and If is a special experience that creates the best kind of memories.

The vessel was commissioned in 1939 by General George S. Patton. He had a dream in mind, to sail around the world alongside his wife, “When the war is over, and If I live through it.” Designed by John Alden, the vessel didn’t fulfill its original purpose, but maintained the bittersweet name that references Patton’s words. After renovating another famous Alden schooner, Doug Hazlitt purchased When and If, renovated it for two years, and made it available to the public. You can rent the vessel and sail all the way to Cuba this summer, starting from Key West, Florida. The spacious decks allow for lounging and sunbathing, while the three private cabins are ideal for families searching for once in a lifetime adventures. Ultimately, the destination is just as special as the journey; as the sun rises and sets the sky on fire, the bright Cuban shore beckons visitors to discover and explore Havana. Whether taken on a regatta or on a private family journey, all the proceeds from renting When and If will go towards bringing General George S. Patton’s dream to life: to sail on a trip around the world. Images courtesy of Sailwhenandif.






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