“We sail not to escape life, but for life not to escape us.”

Our guest, Rusty Carter, shares his experience aboard Sea Witch

We've flown south for the winter. ✈️  Let it snow someplace else and come visit us in the Caribbean!  Or call now to book your Summer 2020 sail in The Vineyard.

Set sail with Sea Witch Sailing Charters and see for yourself why life is better at sea.  Bask in the sea breezes and warm sun, unplug from the stress and rush of daily life, and live the dream for an afternoon, a day or a week.  With the wind in your hair and the warmth of the sun on your skin, you’ll get bewitched by the magic of the sea aboard our sailing yacht.

Based in Martha's Vineyard, Massachusetts, from June to mid-September and the Caribbean Islands from November through April, we offer everything from day sails, to live-aboard vacations, to offshore passages for guests with the right skill set.  In addition, Sea Witch Sailing Charters offers expedition point-to-point sailing opportunities as well as sailing vacations in world-wide destinations such as the islands of the South Pacific, Australia and the Mediterranean.  We will whisk you away to the best anchorages featuring tranquil coves, seaside towns and perfect islands during your time aboard.

Aspire to living your own dream at sea?  We can provide you with opportunities to learn to sail, gain offshore experience and carve a path to fit your future plans.  As a certified American Sailing Association Instructor and 100-Ton Master Mariner, our Senior Captain, John Stephenson, offers not only a genuine, easy personality but also a wealth of knowledge and experience that adds to any sailing trip.  Our support captains, crew and staff offer additional knowledge and experience to provide a well-rounded experience aboard any of our sailing charters.

For more information about any of our sailing vacation options, excursion vogayes or learning opportunities, call or email us!  Wake up from your dreams and live the reality aboard our magical sailing vessel.


From June to mid-September, Martha's Vineyard comes alive with colorful cottages, seaside bistros and long stretches of warm, sandy beaches, and lighthouses like the Gayhead Light (pictured at left).  Click here to learn more about our east coast sailing adventures.

Experience the ultimate adventure with a Caribbean sailing vacation! From November thru April, Sea Witch treats guests to azure blue waters, tranquil coves, hopping beach bars, and just about any water activity imaginable - including boulder jumping at the famous Baths on Virgin Gorda (shown at right).

Click here for more.

Whatever your preference, Sea Witch offers something for everyone.

We look forward to having you aboard!