Sailing on Martha’s Vineyard

Picture of the Sailing Boat the Witch of Endor

The Witch of Endor

As you might expect, on the Island of Martha’s Vineyard sailing is a very popular pastime. Whether you want to take a 2 hour or a sunset cruise, or an overnight or multi-day sailing adventure, Martha’s Vineyard has offerings to fulfill any sailing dream. Regularly scheduled sailings, charters, instructions, and even regattas for the more competitive in spirit are all available.

Martha’s Vineyard Sailing Charters

  • Black Dog Tall Ships, Vineyard Haven, MA – Kids cruises, day sails, and charters. Phone: 508-693-1699. Ships in the Black Dog Tall Ships fleet:
    • Alabama – 90 foot schooner
    • Shenandoah – 108 foot top sail schooner
  • Ena, Vineyard Haven, MA – 34 foot wooden sloop. Charters and sailing instruction. Phone: 508-627-0848.
  • Mad Max, Edgartown, MA – 60 foot catamaran. Daily cruises at 2 PM and 6 PM. Phone: 508-627-7500.
  • Magic Carpet, Edgartown, MA – 56 foot wooden yawl. Daily cruises and private charters. Phone: 508-627-2889.
  • Picture of a Sunset on the Sailboat Sea Witch

    Sunset Aboard the Sea Witch

    Sea Witch Sailing Charters – 58 foot LOA Pearson Ketch Cutter. Charters of 2, 4 ,8 hours as well as overnight, weekend, and week-long charters. Phone: 508-631-6535.

  • Witch of Endor, Vineyard Haven, MA – 41 foot Formosa ketch. 2 hour, 1/2 day, full day, overnight, and multi-day charters. Phone: 508-685-1212.

Martha’s Vineyard Sail Boat Rentals

Picture of a Vinyard Cup Regatta Flyer

Martha’s Vineyard Sailing Regattas

Martha’s Vineyard Yacht Clubs and Sailing Organizations

Other Martha’s Vineyard Attractions / Things to Do

Photo credits: The great picture of the sunset aboard the Sea Witch was provided to us by Sea Witch Sailing Charters.

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