Classic Sail Boston has been showing people the best of Boston Harbor since 2014. Our goal is to make each of our charters a memorable and unique experience for our guests. Whether special occasion or just enjoying an afternoon on the water, we customize and design the perfect environment according to your specifications. Take a moment to click below and read our Yelp / TripAdvisor reviews if you would like to hear our guests experiences and view their photos.
Meet Your Captain
Capt. David Puett's idea for Classic Sail Boston was born from a desire to show people the way Boston ought to be seen, from the water. And what better way than from the decks of a wooden sailboat. A United States Coast Guard licensed Master, he is experienced and knowledgeable in the art of sailing classic boats. David loves to share this knowledge with any looking to learn. Want to get on the lines for some hands on experience? No problem. And, with a passion for Boston Harbor's rich history, you're sure to hear something new about our spectacular city. Whatever your interest be prepared to board as a guests, but leave as a friends!