When and If

North Shore sailing for summer 2024!

Welcome to Sunset Sail Salem, home of New England's finest classic charter fleet and your destination for a truly authentic North Shore sailing experience.

Welcoming Schooner Malabar X for 2024

When and If will be joined by her senior sister, the beautiful Malabar X this Summer as we welcome her into our fleet for the first time. Widely considered to be the magnum opus of John Alden's prestigious schooner portfolio, Malabar X smashed records in the Newport-Bermuda race of 1932 and is available for private charter this Summer with Sunset Sail Salem!

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Get inspired with our most popular trips!

Morning sails

Blow away those cobwebs and start your day right with a morning sail on When And If. Saturday mornings are Mimosa Mornings so let our crew tell you about today’s signature cocktail with a twist, or enjoy a soft drink as we sail into the morning sun.

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Afternoon excursions

The best way to escape the heat on those sweltering Summer days! It’s at least 10 degrees cooler on the water and if there’s a breeze out there we’ll find it. Leave the hustle and bustle behind to join us out in the cool blue where the bright sky meets the dark water as we sail through the afternoon.

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Sunset sails

Take advantage of these long warm evenings and come enjoy a sail on a beautiful historic yacht, plying some of the finest sailing grounds around! Watch the sun set on another lazy hazy summer day as the twilight rolls in and we return to the dock.

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View Our Sailing Trips

Sail away to paradise with our exceptional trips

We are grateful to have such a supportive and loyal customer base, and we hope you will join them in experiencing the Sunset Sail Salem difference.

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Sunset Sail Salem

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.

Come sail on our unique historic yacht and take in the views of Boston's North Shore, the scenic islands, picturesque lighthouses and abundant wildlife as wind fills the sails.

This summer marks our sixth season sailing the beautiful schooner When And If from the Salem landing. Hop onboard as we gracefully sail by up to 5 of Salem Sounds majestic lighthouses while sipping on your favorite cocktail in comfort and style!

When and If

A beautiful classic

The Historic Schooner When And If, built in 1939 for General George S Patton to sail around the world.

"When the war is over, and If I live through it, Bea and I are going to sail around the World" are the worlds of then Colonel Patton as he named his now historic yacht. The elegant classic schooner yacht now takes up residence with Sunset Sail Salem under the care of owner and Captain Seth Salzmann. This vessel is your chance to enjoy truly glorious sailing with room for up to 32 guests on private charters and 28 guests on our shared sailings. Set sail in class and style on this stunning example of the golden years in American yachting under sail!

When and If

Perfect sailing

Escape the crowds and take to the sea for an experience unlike any other. Watch as your experienced captain and crew cast-off lines and the yacht glides out of the harbor. Sit back and relax or lend a hand as we raise sail and turn off the engine. You’ll experience the thrill of the sails catching the wind and the schooner picking up speed as we sail past majestic lighthouse, beautiful beaches, rocky shores and numerous islands in the well protected waters of Salem Sound.

Enjoy from our array of craft cocktails, wines and beer as our Captain and crew share stories of the history of the ship and nautical tales of Salem Sound's storied landmarks and out islands. Misery island, Bakers island, Children’s Island and Marblehead neck are among the many sights to be scene on a regular basis. Keep in mind, that we go where the wind takes us and no two trips are the same!

Our happy customers share their experiences

At Sunset Sail Salem, we pride ourselves on delivering exceptional sailing excursions to our guests. Don't just take our word for it – read what our satisfied clients have to say about their experiences with us.

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“Been onboard multiple times for a few day sails and also booked a private charter for my mom and dad’s 30th anniversary last year. Phenomenal experience every time.”

Ashley Skeffington
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“We had the best sail we could have hoped for. Captain Eric was fun and informative. Will go again and recommend you all do the same. 👍🏻”

Carin Yasli
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“So much fun, and so relaxing. The captain and crew are awesome and really do their best to make your experience amazing. This is a must do.”


Sail into adventure! Our upcoming events

Join us as we set sail and explore the beauty of the open water. Check out our events to see what's coming up and sign up today for an unforgettable adventure on the water!

Sunset Sail on When & If

Set sail on a classic sailing yacht, gliding through the calm waters while the evening breeze fills the sails. The experience of sailing during the sunset is a memory that will last a lifetime

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Private Charter on Malabar X

The beautiful Malabar X, (1930) joins our fleet for the first time this Summer. With space for up to 20 guests and a sailing experience matched only by that aboard her younger sister When And If, a private charter on Malabar is truly the finest classic sailing on the North Shore.

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Private Sunset Sail

An excellent option for those seeking a unique, unforgettable and exclusive experience. Your Private charter can accommodate up to 32 guests .

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Love our Salem sailing excursions?

If you've enjoyed our Salem sailing excursions, you'll definitely want to check out our sister sailing companies!

Sunset Sail Key West

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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When and If

A beautifully restored 1939 John Alden schooner, When and If was designed for American General George S. Patton to sail around the world.