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
When and IfWhen and IfWhen and If

Schooner When And If

This truly classic sailing yacht was designed by renowned Boston naval architect John Alden and launched in 1939 for General George S. Patton. She 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"

When And If is a transoceanic cruising yacht with 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 enjoyed a week's sailing out of Manchester, MA before returning to duty in Europe as acting Governor of Bavaria. He was killed in a car accident shortly after.

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 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.  With her diverse portfolio and busy schedule When And If has become a perfect example of how classic yachting can thrive in the modern age.

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

When and If
When and IfWhen and IfWhen and If

Schooner Malabar X

Before Schooner When And If came Schooner Malabar X: the magnum opus of John Alden’s extensive schooner portfolio. Built in 1930 by Hodgdon Bros of East Boothbay, ME, Malabar X was the last schooner Alden built for himself to win the Newport-Bermuda race which she did with flying colors, smashing records in 1932.

Malabar X was badly damaged and written off in the samestorm which pulled When And If from her mooring and sent her for her rebuild in1990. In like fashion, Malabar X was also painstakingly restored to her former glory and in 2002 was launched sparkling to begin life on the Finger Lakes, NY.

Following her sale in 2003 she spent time as aresident of the Royal Yacht Club in Barcelona and in 2023 was returned to USA to have her flag restored and begin a new chapter as a charter sailing yacht with Sunset Sail Salem.

With her light and elegant silhouette, silver sprung teakdecks, soaring rig and gorgeous interior, Malabar X is the perfect choice foryour Summer sailing charter. She is USCG certified for 37 guests on deck for daysailing, and for overnight trips she accommodates 4 guests in 2 commodious cabins, each with a double berth. A twin V berth in the fo’c’sle and a pilot bunk house the crew.

Come sailing and be part of Malabar’s new life back home in America as we build her a foothold in the classic yachting industry, working to keep these glorious vessels on the high seas for years to come!

When and IfWhen and If
When and IfWhen and If

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 and Malabar X sail fast and smoothly. As the fastest sailboats on the sound we cover a lot of ground wherever the wind takes us and - depending where the wind takes us - on different days can glide by lighthouses, islands, the coastline of Cape Ann, the skyline of Boston. Adventure awaits!

These beautiful antique schooner yachts are equipped with cushioned seating and USCG certified for up to 37 guests, and have a full bar and toilets onboard 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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