Witch of Endor

Sailing Charters

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 have enjoyed sharing our love of sailing with thousands of people over the years through our charter business. Many families return each summer to sail with us, as one of their Vineyard traditions. We also have repeat customers from many local businesses who choose to sail with us for their annual staff parties.

We have had numerous couples get married aboard 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 feel privileged to have been a part of the Vineyard sailing community for the past 25 years.

Sails of 3 hours or longer provide the opportunity to sail for a time and if you like, anchor and enjoy a swim. Many of our guests love destination sails, where we begin in one harbor and end in another, enjoying the views of the coast along the way.

During the many years we have been taking people sailing, we have noticed just how much people really do enjoy the one way excursions. There is less tacking back and forth and the longer reaches can allow for a more relaxing and comfortable ride, and also create the opportunity to see twice as much of the coastal scenery during the same amount of sailing time, giving our guests a feel for the topography of the island. It can be quite novel to step off of your private yacht just in time for your dinner or luncheon reservations in another town.

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 or uber. Popular options include sailing between Vineyard Haven and Edgartown (minimum 3 hours), Vineyard Haven and Menemsha (minimum 5 hours), or Vineyard Haven and Woods Hole (minimum 2.5 hours). We are also happy to discuss other destinations on the Cape or Islands.

Please contact us to discuss the many opportunities to customize your sailing experience.


Sunset Sail (2 hrs) - $550

2 Hour Sail (not sunset) - $500

Half Day Sail (4 hrs) - $800

Full Day Sail (8 hrs) - $1400

One Way Fees:

Vineyard Haven to/from Edgartown - $140

Vineyard Haven to/from Menemsha - $200

Vineyard Haven to/from Woods Hole - $140

Vineyard Haven to/from Oak Bluffs - $100

Vineyard Haven to/from Nantucket - $600

$150/hr after 2,4 or 8 hrs for as long as you like

2 hour sails can be scheduled for any time of day

For groups of more than 6 people, please call the Captain to discuss your options. These include part of your group sailing on our boat and the others sailing on one of our sister ships. Another possibility is the chance to do a destination sail, one of our most highly requested trips, with some people sailing one way to meet your friends and/or family, and the rest of the group sailing back with us on the return trip.

Contact Us For Your Reservation Today!



See Our Rating On Trip Advisor!

Please note that we are only able to serve hors d’oeuvres on charters of 2.5 hours or longer. Thank you for your understanding.


As they say in New England, "If you don't like the weather, wait 15 minutes and it will change!" The weather is extremely variable here and the forecasts can change on an hourly basis. If you have questions or concerns about the weather during the time of your sail, please check the following websites for the most accurate forecasting information.



NOTE: The NOAA site is the marine forecast with wind and sea conditions. Please scroll down until you are looking at the Vineyard Sound section.

Please note weather conditions can affect our pickup and drop off locations.
Weather may require us to make changes to maintain the safety of all our guests.

Pickup Locations

Vineyard Haven Pick Up

Vineard Haven Park And Ride

Edgartown Dock Pick Up

Edgartown Park And Ride

Edgartown Lighthouse Beach Pickup

Menemsha Pick Up

Menemsha Park And Ride

Woods Hole Pickup

Woods Hole / Falmouth Parking Lot

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.

A Conversation About COVID

We are fully vaccinated and boosted. We do have some family members who are in the higher risk categories, so we continue to be cautious and careful. As for life and work aboard Dulcinea, we were already in the habit of a daily 2 hour cleaning procedure, using disinfectant and sanitary wipes. Now we have added further cleaning on all surfaces before, during, and after each charter. During charters, masks remain mandatory inside the boat. While on deck, guests may decide whether or not to wear them given the wind and weather conditions. We want to maintain a safe and healthy environment for our family and our guests. We encourage you to do what feels safe and appropriate for you and your loved ones, and please reach out with any questions or concerns you may have.

Copyright 2021