Edgartown Sailing Charters

Take a 2 hour private sail aboard the restored 1927 catboat “Tigress”

Our 2023 season is open for booking.

We believe that sailing around Edgartown harbor on a catboat is the most relaxing way to experience the island of Martha’s Vineyard. We will sail past the historic Edgartown lighthouse, the Chappaquiddick Ferry, and along the charming shores of Edgartown. While on this scenic adventure under sail, you may even spot some wildlife such as a family of Osprey or a seal swimming in the distance.

Our boat “Tigress” is a restored 30’ wooden catboat built in 1927 by Charles Anderson in Wareham, Massachusetts. Catboats were originally used as workboats for fishing, hauling cargo, or ferrying passengers. Tigress is perfect for exploring Edgartown Harbor and Katama Bay because of her seaworthy hull shape, shallow draft, and retractable centerboard. The wide structure of catboats make them spacious and comfortable for families and friends. Tigress is a sturdy and slow-moving boat, so you will have plenty of time to relax and enjoy the scenery. We also encourage you to bring a picnic to enjoy while you are sailing.

If you are looking for a unique and unforgettable experience, sailing around Edgartown aboard Tigress is the perfect option for your private group of up to six.

Here are some tips for planning your sailing trip:

  • Book your private charter in advance, especially during the peak summer season.
  • Children under the age of 12 are required to wear a life jacket at all times while onboard.
  • Bring sun protection like a hat, sunscreen, and sunglasses. 
  • Bring extra clothing layers because it is usually cooler on the water- blankets are provided.
  • Bring snacks or beverages to enjoy while you are sailing – water, cups, and ice are provided. 
  • Your captain and crew will do everything possible to ensure that you have a great experience. Tips are never expected but are always appreciated.