Sunset Sail Salem

Let us be your Salem, MA sailing experience. We offer day sails and private charters on the beautiful, historic Salem Sound. Take in the views of Boston’s North Shore, scenic islands, and abundant wildlife as the ocean laps against the hull and wind fills the sails.

Sunset Sail Salem will provide your perfect North Shore sailing experience.


Two Beautiful Yachts

Our Friendship Sloop, Wenonah, sails daily with Owner/Operator Captain Eric at the helm. This 30 foot sailing yacht specializes in private sailing charters for up to six guests. Wenonah is modeled after the lobster boats of the early 1900’s, and provides a truly special, classic sailing experience for all who sail aboard.

The historic schooner When And If, built for General George S Patton, takes up residence with Sunset Sail Salem under the care of Captain Dylan this summer. The When And If is a stunning, 1939 John Alden design. This vessel is your chance to enjoy truly glorious sailing with room for up to 30 guests on day sails or private charters.


Your Dream Sail Come True

No matter what type of trip you are looking for, we’ve got you covered.

Book a seat on a day sail or sunset sail aboard the majestic When and If.

For something more tailor-made, ask about a private charter aboard Wenonah. Our Friendship sloop accommodates up to six guests.

Schooner When and If is perfect for larger private groups, accommodating up to 32 people.

We are a small group of sailors who want to share the magic of these beautiful boats with you, and we’ll do everything we can to make your dream sail come true.

Friendship Sloop Wenonah
Sail a New England Classic

Whether you prefer sailing for 90 minutes, 2 hours, half the day or a full day, Friendship Sloop Wenonah is perfect for your private sailing party because every charter is a private charter.

See the local area’s coast, rich in maritime history, the way seafarers did over a century ago on a classic, traditionally rigged Friendship sloop departing daily from Pickering Wharf Marina in downtown Salem. Whether it be for a family outing, romantic getaway, or a fun day with good friends, join us for a classic New England sailing experience.

Schooner When And If
The Historic Ship Built For General George Patton

General George Patton said: “When the war is over, and If I live through it, Bea and I are going to sail around the world.” This magnificent vessel is the peacetime dream of an American war icon, and she was launched with her name full of hope and ambition precluding a destiny as yet unfulfilled.

The fame of this ship arises from her historical provenance and her heartwarming beauty: the meeting of minds between a great military figure and America’s premier naval architect of the time.

Come and be part of her present story! Help raise sail, take a turn at the helm or simply relax and enjoy the gorgeous New England scenery as we harness the fresh summer breezes of Salem Sound and enjoy a trip out on the water.

Most Popular Trips


Historic Schooner When And If

George Patton’s historic schooner yacht, proud to be a guest of Sunset Sail Salem for summer 2019


Shipwreck Ghost Story Sail

Sail over the sites of the North Shore’s most infamous wrecks and hear the chilling histories of the sailors lost below

Photography Sail2

Lighthouse Photography Sail

A beautiful tour of the most picturesque lighthouses in the area – enjoy a unique perspective from the water

for our daily Salem sailing trips

1.5 hr Daysail/ harbor tour on Wenonah$245 for up to six guests
2 hr Sunset Sail on Wenonah$295 for up to six guests
2 hr shipwreck/ghost story sailing tour on Wenonah$295 for up to six guests
3 hr Lighthouse/photography sailing tour on Wenonah$395 for up to six guests
4 hr Island Picnic Sail$550 for up to six guests
2 hr Daysail on When And If $40 per adult, $20/child
2 hr Sunset Sail on When And If$55 per adult, $35/child
2 hr Private Charter Daysail on When And If$1,200 for up to 32 guests
2 hr Private Charter Sunset Sail on When And If$1,650 for up to 32 guests

Soft drinks are provided on all of our trips, you may bring your own adult beverages and snacks. If you have any special requests for food or drinks please don’t hesitate to ask.

Salem harbor from the air. There are hundreds of sailboats in the surrounding bays, channels, and waters.

Contact Us
and book a sail today.

Please contact us to schedule a sailing excursion out of Salem Harbor.

We’re excited to hear from you!

Reach us at (978) 594-6299