Salem’s Friendship Sloop

Friendship Sloop Sunset Sail Salem Starboard Boston North Shore
Wenonah Sailing in the Sunshine

View Our Trips Aboard Friendship Sloop Wenonah

Our beloved Friendship Sloop Wenonah is perfect for relaxing day sails or romantic getaways, picnics on the water, private events and parties. Exclusively available for private charter and certified to carry up to six guests, she is your answer to escaping the summer crowds and sailing out onto the gleaming cool waters of the Sound – Ask about our custom charters to book a longer sail!

The north shore of Boston is home to some of the finest sailing yachts in the country. You will fit right in cruising aboard a recently restored, traditionally rigged Friendship sloop. This beautiful style of vessel has been used in New England since the 1800s, first by lobstermen as a work boat and later as a pleasure craft. Picturesque, private and perfect!

Friendship Sloops
Their History in New England

Friendship sloops have a long history in New England. They were popularized in the late 1800s in Friendship, Maine on Muscongus Bay. Designed like a smaller version of the fishing schooners, they were ideal for hauling looser traps by hand under sail. These slick sloops were the traditional New England lobster boat before after gas and diesel motors took to the seas.

Friendship sloops are gaff-rigged, single-mast sailboats. Each sloop has a full keel, large rudder, clipper bow, and a bowsprit. Wenonah can carry five sails with her topmast. The wooden spar at the top of the mainsail, called a gaff, gives the boat that classic look and allows Wenonah to carry a serious amount of canvas. In light wind or a stiff breeze, the gaff rig grants a sailor the ultimate flexibility and control in the amount of sail to set.

When And If

Sunset Sail Salem’s Summer Guest!

Sunset Sail Key West - Sail When and If - Freas Photography-16.2SM
Whif in Havanasqlg

When and If is a true classic, built in 1939 and the perfect yacht for your sail on the North Shore. On her commissioning, her first owner – General George Patton – said: “When the war is over, and If I return, Bea and I are going to sail her around the world.” As part of a program to enable us to fulfil her destiny, When and If returns home to the North Shore of Massachusetts for another summer with Sunset Sail Salem.

Coastguard certified for up to 32 guests, When And If is your ticket to a spectacular sailing experience under the fresh summer breezes on the sheltered waters Boston’s north shore. Book a seat on one of our shared experience sunset or daysails, or charter the boat for a once-in-a-lifetime private sailing party.

When And If is ideal for your destination wedding, unique family reunion, corporate event venue or team building event – get in touch to ask about private charters.

See Our When And If Trips Here