Top Massachusetts Sailing Tours

Enjoy unparalleled views of the Boston Harbor from the water during this 90-minute sightseeing cruise. Set sail aboard a classic tall-ship schooner. Enjoy plenty of time to ask the captain and crew about local landmarks and Boston’s history. You'll also have plenty of time to relax. Soft drinks and alcoholic beverages are available to purchase, including several beers brewed right in South Boston.

Experience Boston Harbor on a sunset cruise aboard a historic tall ship. Depart from Fan Pier Marina on the 67-foot Liberty Star enjoy views of the outer harbor, Fort Independence, East Boston, the Charlestown Navy Yard, and beyond. Relax and let the crew handle the sails or jump in the action and a grab a line on this fun and affordable outing.

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.

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. Feel free to bring your own food along if you prefer, but please no outside beverages and no coolers. Mimosas are $5 all morning! We also have our full drink menu available including local craft beers, cocktails, wine, soda, juice, and water. We accept Apple Pay, credit cards, or cash onboard.

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this public sail is a perfect outing for family and friends. All ticket proceeds contribute to the World Ocean School's educational programs, ensuring a meaningful experience on the water. Enjoy an enriching day while supporting maritime and experiential education.

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.