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    • Home
    • Our Services
      • Vineyard Day Sails
      • Special Events
      • Off The Vineyard
    • Book Now
    • About Us
    • Photo Gallery
    • Directions
    • Contact Us
    • The Vineyard
    • Policies & FAQ
    • News & Updates
  • Home
  • Our Services
    • Vineyard Day Sails
    • Special Events
    • Off The Vineyard
  • Book Now
  • About Us
  • Photo Gallery
  • Directions
  • Contact Us
  • The Vineyard
  • Policies & FAQ
  • News & Updates

See our Special Events Page for more

Sailing Vacations

Sailing Vacations

Sailing Vacations

Dreaming of getting away from it all, sailing from one island to another, and waking in a new cove each morning?   Captain Wendy's expertise in monohull and catamaran sailing offers you an opportunity to spend your vacation time living aboard a sailboat without the worry of how to sail it.  With 25 years of travel planning experience and a wealth of knowledge about many island destinations, Captain Wendy can offer you a vacation you'll remember for years to come.  

Call or email for more information.

Vessel Deliveries

Sailing Vacations

Sailing Vacations

Need to move your boat from one destination to another but don't have the time or the training to do it yourself?  Captain Wendy offers point-to-point vessel delivery service.  In addition to a USCG Master Captain's License, Captain Wendy is also certified in STCW and Officer in Charge of Navigational Watch.  She has additional crew to help with deliveries, all of whom have thousands of ocean nautical miles, STCW credentials, and experience; plus most have Captain's Licenses as well.  Call or email for more information. 

Instruction

Sailing Vacations

Instruction

Interested in learning to sail?  Captain Wendy is the only American Sailing Association Certified Instructor on Martha's Vineyard.  She can offer you and your friends sailing instruction during any of our sailing charters or charter vacations.  


For more advanced training, we offer destination sailing training with trips from the Caribbean to the US East coast.  Learn about offshore sailing, liveaboard cruising, weather & routing and much more. 

Call or email for more information. 

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We sailed south for the winter

We'll reopen on May 26, 2023. Use our "Book Now" button to reserve your sail for our 2023 sailing season.

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