Salem’s own charter sailboat.

When And If

Sunset Sail Salem’s Summer Guest!

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 and dive in!

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 the area since the 1800s, first by lobstermen as a work boat and later as a pleasure craft. Picturesque, private and perfect!

When and If is a true classic, built in 1939 and the perfect ship for your boat trip 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 a summer with Sunset Sail Salem.

Coastguard certified for up to 28 guests, When And If is your ticket to a spectacular sailing experience under the fresh Summer breezes on the sheltered waters perfect for North Shore sailing. Book a seat on one of our shared experience sunset or daysails, or push the boat out for a once-in-a-lifetime private charter.

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.

Check out availability for a private trip on Wenonah

Book your seat on When And If this Summer