Best Day Ever

The Best Sailboat Companies on Nantucket Island

by California Chaney
The Photo courtesy of The Blue Peter.

NANTUCKET — Is there any greater feeling in the summertime than pulling up anchor and setting sail for an adventure at sea? Swaying to the rhythm of the boat's slow rock, feeling the coastal breeze on your face, allowing the destination to be determined by the winds.

Thirty miles off the southern coast of Cape Cod, Nantucket Island is a seafarer's paradise. Nicknamed "the little grey lady of the sea," the curved, fourteen-miles-long and three-miles-wide island charms and delights with endless sandy beaches, surf breaks, miles of bike paths, quaint lobster shacks, and weathered, shingle-style houses to pile the whole family into. But to truly embrace the remote island's beauty, it's best to throw off the bow lines, cruise past Brant Point Lighthouse, and sail into the Atlantic.

These are the outfitters we trust to turn our Nantucket sailing fantasies into reality.

Photo courtesy of The Blue Peter.

The Blue Peter
Greydon House is a former sea captain's house that's been converted into a charming, 20-room boutique inn. The hotel partners with Mat Barker, owner and captain of The Blue Peter for four-hour private picnic lunches and sunset champagne charters for up to six guests. A rare and majestic classic built in the 1930s from teak originating from Thailand in 1870, she (boats are powerful ladies) was named after the nautical flag used as a preparatory signal before a race. The 65-foot sailboat is perfect for sailing enthusiasts who aren't afraid to take over the ropes or tackle a jib. And although guests are encouraged to skipper or take the helm, it's equally encouraged to sit back and sip champagne. Barker has sailed the Atlantic six times since restoring the boat in 1999 and delights in sharing tales from his voyages into the deep blue.

Nantucket Mermaids
These ladies at sea offer the largest fleet of sailboats and yachts, including catamarans, Hinckley picnic boats (the Nantucket classic cruiser), sailboats, luxury sports fishing, and even a 90-foot houseboat for larger events and cruises.

Photo courtesy of White Elephant.

James Genthner, better known at sea as Captain Jim, has been sailing the Nantucket harbor for over 40 years and runs the longest operating sailing charter on the island. So let's just say he knows a thing or two about local maritime history. He offers 90-minute tours in the afternoon and at sunset on Endeavor, the sailboat he built himself. 

Barton & Gray
Through an exclusive partnership with the members-only yacht club, guests of White Elephant Resorts (the collection includes the newly renovated White Elephant, The Wauwinet, Jared Coffin House, and The Cottages at the Nantucket Boat Basin) can charter classic Hinckley yachts to cruise the intracoastal and Coskata-Coatue Wildlife Refuge – a remote area on the northern point of the island.

Photo courtesy of The Wauwinet.

Wauwinet Lady
Nestled on the northeast shore of the island, The Wauwinet offers cruises to White Elephant for lunch and dinner aboard Wauwinet Lady, their private water taxi. On a slow, scenic cruise along the shoreline, captain Rob McCullen stops to check up on the Retsyo Oysters that are cultivated mere yards from Wauwinet. Free champagne is given to the best shucker on board.

Keep Exploring Nantucket

A Nantucket Guide for All Seasons (But Especially the Summer)
The Great Sail: Nantucket to Menemsha
Insider's Guide to Nantucket's Beaches

We make every effort to ensure the information in our articles is accurate at the time of publication. But the world moves fast, and even we double-check important details before hitting the road.