Capacity 6

Private Charters from $545
Sailing Charters For Up To 6 Guests Around Boston Harbor & Islands

Boston Sailing Tours offers private sailboat charters in the Boston Harbor and the Boston Harbor islands. We offer relaxing private tours of the inner harbor where you can enjoy your favorite food and wine for your special occasion and also extended sailing tours and exploration of the islands that are only accessible by private boats. Consider booking one of our private sailing charters for an unforgettable experience.

With a variety of options available, you can relax and take in the stunning views of the city skyline or go on a sailing adventure to the harbor islands where you will see deer, wild life, and enjoy magnificent beaches with no one around.

We are the only sailing tour operator who can take you to Lovells, Grape, and Bumpkin Islands and allow you to explore these islands as part as your charter.

This unique sailing experience promises to provide you and your guests with a memorable and breathtaking journey through the beauty of Boston Harbor and its islands.

2 Hour Daytime / Sunset Sail

Spectacular views of the Boston Harbor skyline, a very relaxing sailing experience for your special event. The perfect stage for a unique moment… Birthdays, proposals, memorials, or simply cruising along.

This is a complete tour of the inner harbor. You will sail by the USS Constitution, the North End, the Seaport District, Castle Island, and East Boston.

Full Day Sailing & Island Experience

We will sail to the islands that are not accessible by ferry. Depending on the wind, tide, and your preferences we will stop at Lovells, Bumpkin, or Grape islands.

There is, most of the time nobody, or very few people on the islands. You will get to spend a few hours a shore while the boat will be waiting for you.

On the way back, we will take a different route. At all times you will be welcome to participate in the navigation.

Melissa Carvalho

Charter Manager