Ranked #1 on TripAdvisor 2018, 2019, 2020 & 2021

Sea Witch Sailing Charters
  • Welcome
  • Our Services
    • Martha's Vineyard
    • The Caribbean
    • Our Sister Ship
    • Other Services
  • About Us
    • Our Vessel & Crew
    • Reviews
  • FAQs & Polcies
  • Contact Us
  • More
    • Welcome
    • Our Services
      • Martha's Vineyard
      • The Caribbean
      • Our Sister Ship
      • Other Services
    • About Us
      • Our Vessel & Crew
      • Reviews
    • FAQs & Polcies
    • Contact Us
Sea Witch Sailing Charters
  • Welcome
  • Our Services
    • Martha's Vineyard
    • The Caribbean
    • Our Sister Ship
    • Other Services
  • About Us
    • Our Vessel & Crew
    • Reviews
  • FAQs & Polcies
  • Contact Us
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Sea Witch Sailing Charters

Sea Witch Sailing ChartersSea Witch Sailing ChartersSea Witch Sailing Charters

"We sail not to escape life, but for life not to escape us."

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Set Sail with us and see why life at sea is better

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 voyages or learning opportunities, call or email us!  Wake up from your dreams and live the reality aboard our magical sailing vessel.


Whatever your preference, Sea Witch offers something for everyone.  We look forward to having you aboard!


We are fully compliant with all current regulations for charter boats and carry a maximum of 6 guests per U.S. Coast Guard Code of Federal Regulations, Subchapter C.  Visit our "Services" page for options for more than 6 guests.

508.631.6535

There's much to see here. So, take your time, look around, and learn all there is to know about us. We hope you enjoy our site. Take a moment to drop us a line or give us a call.

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New Options for Groups Larger Than 6!

Check out The Vineyard's Newest, Exclusive Sailing Option

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