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.
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
- Island Water Sports, Vineyard Haven, MA. Phone: 508-693-7767.
- Winds Up, Vineyard Haven, MA. Phone: 508-693-4252.
Martha’s Vineyard Sailing Regattas
- Edgartown Yacht Club 12 Metre Regatta – Held in August.
- Edgartown Yacht Club Regatta – Held in July.
- Edgartown Yacht Club ‘Round the Island Race – Held in July.
- Moffett Race– Held the Saturday after Labor Day.
- Vineyard Cup Regatta – Held in July.
- Vineyard Haven Yacht Club Junior Regatta – Held in July
Martha’s Vineyard Yacht Clubs and Sailing Organizations
- East Chop Yacht Club
- Edgartown Yacht Club
- Holmes Hole Sailing Association
- Sail Martha’s Vineyard
- Vineyard Haven Yacht Club
Other Martha’s Vineyard Attractions / Things to Do[catlist orderby=title order=asc name=marthas-vineyard-attractions numberposts=30]
Photo credits: The great picture of the sunset aboard the Sea Witch was provided to us by Sea Witch Sailing Charters.