Boston Sail Tours... Looking for a unique way to explore the beauty of Boston Harbor and the surrounding islands? You can go ahead and book a private sailing charter for an unforgettable experience. With various options available, you can customize your adventure and sail in style while taking in the stunning views of the city skyline and the natural wonders of the harbor and islands. Experience the beauty of Boston Harbor & Islands like never before with Boston Sail Tours. Book your private adventure today, May to October aboard the classic sailing vessel Francesca for up to 6 guests.