Welcome to the Schooner When And If. Built in 1939 for General George S. Patton, When And If was commissioned by Patton himself from naval architect John Alden, and built by FF Pendleton in Wiscasset, ME to sail around the world “When the war is over, and If I live through it.”
When And If is currently finishing out her Winter season in Key West, FL before preparing for a busy Summer as a popular sailaway vessel at Tall Ships Great Lakes 2025.
Explore the water with our sister companies. Whether you're a seasoned sailor or a first-timer, our excursions have something for everyone.
Sunset Sail Key West is more than just a private sailing charter, it is the culmination of decades of experience and a lifetime of passion for sailing, and for Key West.
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Salem and the North Shore are home to some of loveliest sailing in New England. We offer daily sailing and private charters on the beautiful Salem Sound.
When And If sails all year round: out of Key West, FL in the Winter and Salem, MA in the Summer. With our wide range of custom private charter options as well as our a la carte shared sailing availabilities, you’re sure to find your dream sail on this beautiful classic schooner yacht.
Whether it’s a morning excursion, an afternoon on the water or a sunset sail, When And If offers an unparalleled sailing experience on a gorgeous historic schooner; see and be seen as you sail in style.
Welcome to our photo gallery! We hope the photos inspire you to join us on one of our voyages and create your own unforgettable memories out on the sea.
With her storied past, productive present, and bright future, When And If has a narrative all her own. She was commissioned by General George S Patton from the illustrious naval architect John Alden, and built by FF Pendleton of Wiscasset, ME to sail around the world “When the war is over, and if I live through it.”
Her sturdy construction of double planked mahogany over black locust frames and an oak keel made her heavier than Alden’s signature racing schooners, more suited to her transoceanic cruising agenda. She was launched in November of 1938 and in 1939 Patton took delivery of her to Massachusetts where the Patton and Ayer families lived. Shortly thereafter, Patton was deployed in Europe. He returned on leave at least once to sail the boat in his home waters of the North Shore of Massachusetts with his family. Many boats during World War Two, particularly wooden vessels, were requisitioned as sub hunters for the United States Navy though When And If seems to have escaped this fate and saw out the war in safety. Patton was killed in a car accident in Germany in 1945, shortly after the armistice, and his vision to sail around the world on the boat remains unfulfilled to this day.
When And If remained in the Patton family until 1972, when she was donated to the Landmark school for children with Dyslexia in Pride’s Crossing, MA. Patton himself was dyslexic and When And If’s time there marked some of the happiest years for children at the school. Today they come sailing and visit the boat both in Massachusetts and Florida, bringing their own families to regale them with their sea stories never forgotten from all those Summers ago.
In 1990 a vicious nor’easter tore When And If from her mooring and put her up on the rocks at Pride’s Crossing. She appeared mortally wounded, with a hole in her port side “you could drive a VW bug through” and all hope seemed lost until a pair of shipwrights from Martha’s Vineyard purchased the wreck and barged her over to Vineyard Haven to give her a new lease of life.
In 1994 to she was launched, sparkling, from the railway at Gannon and Benjamin, earning them industry-wide recognition for their fine craftsmanship and traditional values in shipbuilding.
Following a stint as the belle of Vineyard Haven harbour, When And If passed into private ownership for a time and in 2011 was purchased by Doug Hazlitt who, after his restoration of the Alden racing schooner Malabar X, purchased When And If prepared to undertake the second big rebuild of her life.
After X years, with a gleaming new sprung teak deck among the most prominent of her new adornments and her length restored to the original 63.5 ft from the 63 it had become during her previous rebuild, When And If once again splashed and lay in wait for her next adventure.
Captain Seth Salzmann had a special place in his heart for When And If. He remembers the first time he saw her in Penobscot Bay, ME in 2006 and though he knew almost every boat in those waters he didn’t recognize the new visitor. “It was like when you see a girl for the first time” he says.
In 2015, after he had managed a large portion of When And If’s 2012 refit, Seth couldn’t resist the opportunity to lease her and begin her new life as a sailing charter boat.
After a summer in Hyannis, MA and a winter in Key West, FL When And If spent the Summer of 2016 touring the Great Lakes for the Tall Ships Festival there before found her new Summer home the following year in Salem, MA.
During this time the opportunity arose for Seth to buy the boat and in 2017 he became owner/operator of his treasured vessel.
Seth’s ambition has always been to fulfil When And If’s destiny and sail around the world. Now with a young family in tow the focus is on keeping the boat busy and raising her condition, ready for that time in the not-too-distant future when her great journey will begin.
