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Cape Sailing Charters

Cape Sailing Charters


About Us

Cape Sailing Charters is your guide to connecting with what Cape Cod is truly about: a link to the marine world and the rich maritime history of this place. Situated on the elbow of Cape Cod where Nantucket Sound meets the Atlantic Ocean, quaint and historic Chatham is the perfect port from which to sail. Captain Chris Sammartino grew up sailing these waters and has been leading sailing charters out of Chatham since 2000. Our 38-foot sailboat, Hannah, is a safe, spacious, and beautiful vessel. We look forward to having you sail with us!

Your group of up to six people has private and exclusive use of Hannah for the duration of your charter. This means whether you’re envisioning a fun family excursion, a romantic sunset sail, or gathering with good friends to share stories and a bottle of wine, Hannah is all yours. Coming aboard is as easy as stepping off the Chatham town dock at Stage Harbor and onto the boat, an ideal setup for children and elderly family members.

We specialize in personalizing your onboard experience. We’ve celebrated birthdays and retirements, seen marriage proposals, served as a unique photo shoot locale, whisked brides and grooms off into married life, and more. We'd love to have you aboard.


  • Sailing into Nantucket Sound from Stage Harbor, Chatham
  • Private Charters - 6 passengers maximum
  • 2 hours to all day - it's up to you!
  • Sunset Cruises
  • Family Adventures


Cape Sailing Charters: Slowing Down the Speed of Life
Come Sail With Us!
She Said Yes!
Up on the Bow With Cape Sailing Charters
No filter needed with Cape Sailing Charters
Bring us that breeze!

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