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 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.

About Your Vessel 'Captiva'

Captiva, our new flagship, 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 even dancing if you like! We love taking photos of our guest amidst the old rigging and lines with the beautiful Boston skyline as a backdrop.  We look forward to having you aboard!

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 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!