When and If

Memories that last a lifetime

From the stunning views of Salem Sound's off shore islands to the experience and warm hospitality of our crew, we offer unforgettable sailing experiences onboard our Historic Schooner Yacht When And If.

When and If
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Schooner When And If

A truly classic sailing yacht which was designed by John Alden, a renowned Boston naval architect and launched in 1939 for General George S. Patton, the famous World War II General. The yacht was named after a quote attributed to Patton, who said "When the war is over, and if I live through it, Bea and I are going to sail her around the world"

The Yacht has a traditional wooden hull, teak decks, and a gorgeous rig with tall masts and a multitude of sails. She is known for her beauty, speed and exceptional sailing performance. Before World War II, Patton made just one voyage aboard - Taking delivery in Wiscasset, Maine and sailing to the Chesapeake bay, where it is said that the vessel hid in an estuary to escape the call to join the USCG picket patrol. General Patton returned briefly in the summer of 1945 and experienced a weeks long sail from Manchester (by the sea) Massachusetts before returning as acting Governor of Bavaria and subsequently passing away from his injuries in a car accident.

The Schooner When And If, operated by Sunset Sail Salem in the summers and Sunset Sail Key West in the winter months has spent much of her long life in the waters of the North Shore and surrounds: first as part of the Patton estate in the 1940s, 50s and 60s, then as part of the Landmark School at Pride’s Crossing in the 1970s and 80s, and afterwards as the darling of Vineyard Haven in the 90s.

In 2012 the yacht was restored to her original lines by then owner Doug Hazlitt and current owner Seth Salzmann as Captain and project manager. In 2016 Capt. Seth purchased the yacht, and has been opened her to the public for the first time in her storied history. When And If is available for Private and public sailing charters, regattas, film and photo shoots and tall ships festivals year round. The When And If has become an iconic symbol of classic yachting history!

We are proud and happy to be running her in her home waters once again!

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About us

We sail all summer long, rain or shine out of Salem, MA running award-winning sailing tours in the beautiful waters of the North Shore. With a full schedule of morning, afternoon and sunset sailing plus unlimited options for private charters, we’re sure to be able to bring you out on your perfect sailing trip this summer. Would you like to add an extra hour or two? Do you need your trip catered? Call us to make your dream sail come true!

When and If sails fast and smoothly. As the fastest sailboat on the sound we cover a lot of ground wherever the wind takes us and on different days can glide by lighthouses, islands, the coastline of Cape Ann, the skyline of Boston. Adventure awaits!

This beautiful antique schooner yacht is equipped with cushioned seating and USCG certified for up to 32 guests, a full bar and toilets on board to afford you every comfort during your time with us. Take a look at our full schedule of trips and book online or get in touch to talk to us about a custom private sail for you and your friends.

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