What We Do

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 do all we can to create the sail you're looking for.

Our Vessels Captiva & Seguin

Captiva is a 45 foot Classic Chesapeake Skipjack. Built in 2011, she was crafted to the specifications of the 1890's version. Known for its spacious decks and stability, the "Skipjack" makes a perfect classic sailing charter boat. She was custom built generously using mahogany, teak, obeche and other exotic woods. With ample deck space for moving about, setting up a picnic, or just lounging.

Seguin is a fully restored 26 foot 1967  Chris-Craft Cavalier Cutlass. The newest addition to our fleet, she boasts gorgeous mahogany and plenty of room for guests to enjoy from the bow or deck. Small but mighty, a big 357 engine allows for quick access to the inner harbor, outer islands, lighthouses, up the Charles River and everything  in-between. This cutie has all the charm of a classic antique motor vessel.


Meet Your Captain

Capt. David Puett's idea for Classic Sail Boston was born from a desire to show people the way Boston is best seen, from the water. And what better way than from the decks of a classic wooden boat. 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 interests, be prepared for an exceptional experience on Boston Harbor