About Us

The Sailing

 Coming to the Vineyard and missing an opportunity to sail on this 105 ft puppy  would be like visiting Niagra Falls, NY and not seeing a waterfall.

See and Feel the Islands......under Sail. It just doesn't get any better than this. Come back refreshed, inspired and ready to take on the world with a new and healthier perspective. Make it happen. You and your family and friends, on vacation, deserve no less.​


Menemsha offers some of the best sailing on the planet as well as being uniquely situated to have (on the Eastern seaboard) sunsets over the ocean and the alluring  Elizabeth Islands.


The Elizabeth Islands, remote and pristine, seductive, unknown (but from a distance) ......these are what make Vineyard Sound the protected, sailing paradise it has come to be. Feel the excitement and what it's like, up close, to sail between and brush through and around these glacier-made gems, through colorful and narrow, challenging passageways and crystal clear channels leading through Quick's Hole and Robinson's Hole from Vineyard Sound into Buzzards Bay..... then back-around-through again, heading home.......under the glory of sail. 

These are the stomping grounds for "Mass Transit 105," a gorgeous, powerful, mega-yacht with finely tuned, in-line five spreader mast, and fractional (7/8) rig; the perfect, efficient wind machine and companion for such a setting.  She has been custom designed and hand built (by captain himself) for your sailing pleasure.


At Sailing Martha's Vineyard we offer both the ultimate Sailing experience and a hardy Vineyard experience combined,  a virtual "2 fer 1," guaranteed to be the highlight of your island vacation, for sailors and non-sailors alike. Guaranteed. 

Please scroll up to the menu at top to learn more about the boat, the captain and crew and the many different sailing options we offer, tailored to your individual needs and budget.