Sail Away to the Vineyard.

Arabella
Depart with up to 42 of your associates from the quaint fishing village of Menemsha, and sail to Cuttyhunk, one of the Elizabeth Islands, with Captain Hugh Taylor (of the famed musical Taylor family) aboard his classic 50-foot catamaran. Enjoy his easy-going tour of waters and wildlife and then spend the day where time seems to have stood still. If your day is already filled, why not take in a sunset sail and let Captain Taylor and his crew share their love of Vineyard waters while you enjoy cocktails and light fare on the open seas. Private charters available.

Mad Max
Sail Edgartown Harbor and its surroundings aboard this 60-foot state-of-the-art catamaran, departing three times daily on regularly scheduled tours. Private charters are available. Coastguard approved for up to 49 passengers, guests can enjoy the sun, wind, and water on the vessel’s spacious decks or in the comfort of the shaded cabin. Add snacks and beverages, then just sit back, relax and enjoy the ride.

The Alabama & The Shenandoah
Be welcomed aboard one of these wind-jamming schooners for the experience of a lifetime. You will be swept away into the bygone era of wooden ships and pirates. At 90 feet and 108 feet respectively, the Alabama and the Shenandoah are like no other vessels, with no auxiliary power. Luckily our area is blessed with reliable southwesterly winds. Both boats boast a full galley kitchen and we’d love to cater your reception, luncheon or dinner for up to 49 sailors!

Private Boats
Smaller groups of 6–15 people can charter several exquisite classic sailing craft, based on size and availability.

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