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.