Witch of Endor Sailing Charters

Martha's Vineyard, MA

Let us show you the beauty of Martha's Vineyard from the water. Explore the lovely harbors of the nearby Elizabeth Islands and Cape Cod coastline. We offer instruction, hands on sailing, private catered parties, or just the chance to relax, sit back and enjoy the wind and waves.

All charters include bottled water, ice, fresh chilled fruit (organic when available), gourmet cheeses, dried meats and a fresh French baguette. Please note that safety is always our main priority, so if it is blowing 18 knots or above, we may not offer the hors d'oeuvres.

We also offer one way sails, which are very popular. Sails of 3 hours or longer provide the opportunity to sail for a time and if you like, anchor and enjoy a swim. 4 hours allows enough time for a swim and/or a meal on board. Instead of leaving from and returning to the same harbor, consider a destination sail, where you step aboard in one harbor, sail all along the coastline, gaining a new appreciation for the beauty of the land as seen from the ocean, and step off your private yacht in a different port, ready for luncheon or dinner reservations.

To return to your lodgings, there are many options - leave a car ahead of time in the destination harbor, use the excellent public bus system or hire a taxi. Popular options are sailing between Vineyard Haven and Edgartown (approximately 2.5 - 3 hours), Vineyard Haven and Menemsha (about 4 hours), or Vineyard Haven to Woods Hole (about 2.5 hours). We are also happy to take you wherever else you might like to go!

Many of our guests love the destination cruise, as they have the opportunity to enjoy viewing more of the coast from one harbor to another. Please contact us to discuss the endless options for customizing your sailing experience.

On March 3rd, 2018, we experienced every boat owner’s worst nightmare - an unexpectedly violent storm caused our beloved sailboat “Witch of Endor” to break free of her mooring and wreck on the concrete pilings of a nearby dock. We had visited the boat the day before and checked all of our mooring lines and chafing gear, but the strong storm surge was too much even for our oversized lines. We have enjoyed sharing our love of sailing with thousands of people over the years through our charter business. Many families return each year to sail with us, as one of their Vineyard traditions. We also have repeat customers with many local businesses who host their annual staff parties aboard. We have had four couples get married on the Witch over the years in small, intimate ceremonies full of love. We have been honored with the scattering of loved ones’ ashes at sea several times, and have had all ages, from babies to great-grandparents, enjoy sailing with us. We have donated many charters over the years to causes such as the Possible Dreams Auction on MV and The Children’s Trust in Boston.

We are happy to announce that after an extensive search, we have found a new boat to sail and enjoy with our guests. She is a 42’ Tayana Vancouver in beautiful condition, ready for this sailing season. Her name is “Dulcinea”, which means sweetheart. We look forward to introducing her to our new and returning charter guests and friends.

SUNSET SAIL (2 hrs) $400

HALF DAY SAIL (4 hrs) $600

FULL DAY SAIL (8 hrs) $1000

$100/hr after 2,4 or 8 hrs for as long as you like

Sunset sails can be scheduled for any time of day





Vineyard Haven


Up Island




Cancellation Policy - There is a 20% service fee for any cancellations. Refunds are available with 30 days notice of the reservation date. If cancellations are made with less than 30 days notice, we will do our best to rebook the charter. If we are able to rebook the date the deposit will be refunded, less the service fee. If we cannot rebook the date the deposit is then forfeited. No refunds will be given for late arrivals or early departures. Rain shall not necessarily constitute a reason for cancellation or rescheduling. In the case of extreme weather, the Captain and Charter guests shall attempt to find a mutually convenient date to reschedule the charter. If rescheduling is not possible, the 20% fee may still apply. It will be up to our discretion based on the specific scenario. Since we are in a marine environment we suggest that all electronics, including cell phones and computers, be stowed away for your protection. Witch of Endor Sailing Charters cannot be held responsible for water damage to your possessions.