Paddle boarding in the Ocean

Boating on Nantucket


Sailing and boating are such a big part of Nantucket's culture, and many of our guests want to get out on the water during their time on the island. From cruising the bay at sunset to exploring for the day, we've got three recommendations for boating on Nantucket. Next time you're visiting Nantucket, get a different look at Nantucket by going out on one of these boating charters.


Endeavor Sailing | Straight Wharf, Nantucket | (508) 228-5585

You may see this picturesque sailboat cruising the waters of Nantucket when you arrive. The Endeavor is a Friendship sloop, a style of sailboat once used for fishing in Maine and Massachusetts. Endeavor was built by Captain Jim, who now runs charters, taking groups out for a sail around Nantucket Sound four times a day. Help set sail, take a turn at the helm, or just sit back and take in the beautiful sights of Nantucket during this sailing trip on Nantucket.

ACK Sail | 34 Washington St., Nantucket | (508) 423-9985

Looking for a more private experience? Book a trip on a Private Chartered Sailboat that can be chartered for afternoon and sunset sails. The captain will set sail for Nantucket Sound, going wherever the wind takes you and sharing his local knowledge of the area. Bring along drinks and snacks and enjoy the boat to yourself, on this private sailing charter on Nantucket.

Nantucket By Water | Straight Wharf, Nantucket | (508) 228-7037

From whale watching to sunset cruises, this charter company, formerally known as Shearwater Excursions, has a trip for all ages and interests. Poke around the harbor and learn all about grey seals or hop off on a sandbar and dig for clams. Or sightsee with a drink in hand on board the cocktail or sunset cruise. Most trips take place on Minke, an adorable 26-foot launch with a canopy, while the whale watch trip is on a comfortable 47-foot power catamaran, perfect for spotting a number of whale species off Nantucket.

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