Located 30 miles off the mainland coast and surrounded by the Atlantic, boating is one of the best ways to experience Nantucket Island. Charter a boat to explore the pristine waters, embark on a seal and whale watching excursion, or board a Hinckley yacht for an afternoon harbor cruise. Interested in navigating these waters yourself? Nantucket Community Sailing can help with that, offering lessons and rentals for voyagers of all ages! Whatever nautical adventure you crave, our beach hotel concierge can guide you in the right direction and assist with recommendations.


Nantucket Community Sailing:

Learn the skill of sailing and allow it to foster confidence, independence, teamwork and sportsmanship, all while engaging in the island’s exceptional marine environment. Both group and private sailing programs and boat rentals are available to people of all ages and skillsets, with locations at Polpis Harbor, Jetties Sailing Center and Children’s Beach Pier. Recognized by US Sailing for “Outstanding Seasonal Program” and “Outstanding Outreach and Inclusion.”


Nantucket Mermaids:

Enjoy all of the yachting perks – without any of the headaches – on a private Hinckley cruise around the harbor. Nantucket Mermaids is run by Leah Collins, who had years of experience as Chief Stewardess on mega yachts 150 plus in both the Caribbean and Mediterranean. With over 19 years experience living in Nantucket, Leah has a professional team that can do anything for the Islands many private boats, to working to fulfill any request a visiting yacht may require.


Endeavor Sailing:

Join U.S. Coast Guard Captain James Genthner for a beautiful and informative excursion aboard the longest operating sailing charter on Nantucket, where you’ll learn of the islands diverse maritime history while taking in the stunning coastal sights.


Shearwater Excursions: Seal & Whale Watching:

The first of its kind, Shearwater Excursions is a local family-run Eco-tour company providing memorable and educational experiences for all ages. In addition to seal and whale watching expeditions, the outfit offers harbor and sunset cruises, whaling history tours, clamming excursions and kid’s fishing trips. Shearwater’s close ties with many nationally recognized research organizations ensure passengers receive exceptionally educational tours.


Nantucket Regattas

Figawi Race Weekend:

Kickoff the summer racing season with the Northeast’s first major regatta, where over 200 boats and a thousand sailors compete in the Cape-Nantucket Figawi Race, recognized internationally as a top sailing event.


Nantucket Race Week:

Nantucket Race Week is nine days of regattas, awards ceremonies, and parties hosted by Nantucket Yacht Club and Great Harbor Yacht Club to benefit Nantucket Community Sailing. Sailors of all ages and abilities are encouraged to participate in this community-wide, beloved Nantucket tradition. Nantucket Race Week is a Clean Regatta as certified by Sailors for the Sea.


Opera House Cup Regatta:

The Opera House Cup marks the triumphant finale to Nantucket Race Week, attracting some of the finest, most revered boats in the country. The first all-wooden, single-hulled classic boat regatta on the East Coast, the Opera House Cup is a beloved tradition on Nantucket, enhanced further by the rainbow fleet escort of all competing boats to the starting point.

explore more