Top Massachusetts Sailing Tours

Spend two hours sailing on the Boston Harbor as the sun goes down, taking in the sights of the city skyline. Your captain will set sail and take you on a smooth cruise along the waterfront in a comfortable schooner, with a friendly and informative crew who’s happy to help you have the best possible experience while you’re on the water.

See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Snap photos of Boston's coast from the water and feel free to ask the captain or crew questions about the passing landmarks.

Set sail on a private catamaran adventure aboard the Fountaine Pajot Mahe 36 Evolution, designed to accommodate up to 6 guests or more with prior arrangement). Captained by the knowledgeable Capt. Lu, enjoy the scenic Gloucester Harbor and rugged Cape Ann coastline in a relaxed atmosphere. This sailing experience is perfect for families, couples, and small celebrations, providing ample space to unwind and explore at your own pace. - Experience Gloucester's coastline from a spacious 36-foot catamaran - Tailored trips for special occasions like birthdays and proposals

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are welcome aboard. Whether you crave adventure, relaxation, or both, our charters promise a tailored maritime experience. Set sail with us and make lasting memories on the open water! Skip the bridge traffic, tourist traps and parking nightmares and visit a quiant New England coastal village instead. We are located at the Mattapoisett Boatyard, about 5 minutes off I - 195. Our itineraries depend on how you want to spend your time on the water. Whether you are looking for a sporty sail in the bay or a quiet cruise along the picturesque shoreline we will make your day. We also specialize in Bachellorette and engagement parties, wedding launch services, regattas and spectator fleet.