Explore Boston

6 Ways to Sail Away in Boston Harbor

From city skyline to untouched island, Boston Harbor views are dramatic, even more so as summer moves into fall

It might be the 21st century, but clippers, schooners, sloops and other sailing vessels still navigate Boston Harbor lending it the air of a bygone time. Eschew a typical harbor cruise and instead opt for something a little more majestic. You might hoist a sail or enjoy a lobster dinner, but you'll definitely experience New England maritime heritage.

Classic Harbor Line

Departs: Rowes Wharf

Classic Harbor Line's majestic 1890s-style wooden pilot schooner Adirondack III carries about 40 guests and cuts a clean line through Boston Harbor. Public voyages include day, sunset and city lights sails, as well as occasional specialty trips like the Boston Harbor Islands picnic sail and a Saturday morning mimosa-studded one.

Liberty Fleet of Tall Ships

Departs: Long Wharf

Help the crew haul a sail aboard the Liberty Fleet's 125-foot Schooner Liberty Clipper or her little sister, the 67-foot Schooner Liberty Star. Regular day and sunset sails and Sunday brunch trips are interspersed with the lively Boston Tea Party Reenactment and the historical Rum & Revelry Cruise for the 21+ crowd.  

Come Sail Away Now

Departs: Fan Pier Marina

On Come Sail Away Now's more intimate voyage that has the waters of the harbor lapping at your shoulders, Captain Don commands the 31-foot traditional gaff rigged friendship sloop Tupelo Honey, which seats about 12 for a Sunday afternoon public sail (or any day for small groups that want to schedule private ones).

World Ocean School

Departs: Fan Pier Marina

Built in 1925 in Essex, Mass., of white oak, World Ocean School's Schooner Roseway is one of only six original Grand Banks schooners and is now a National Historic Landmark. In the summer, it provides an educational environment for youth, but it also hosts the public at special events like beer tasting sails and the signature "Sunday Funday" event.

All Hands Sailing Charters

Departs: Constitution Marina, Charlestown

All Hands Sailing Charters captains Bob and Linda navigate Boston Harbor aboard the Argon. The 40-foot Tartan sloop accommodates up to six passengers for chartered two-, three- and six-hour harbor tours, one-way trips to destinations along the Massachusetts coast, or to favorite swimming spots. 

Sail Boston Harbor

Departs: Rowes Wharf or India Wharf

Boston Light, Sail Boston Harbor's Bristol sloop rig, dates back to 1970; aboard it, organize your own, personalized adventure with a few friends, whether it's a full-day cruise or the opportunity to weigh anchor at one of the harbor islands. You can also get as involved as you want, steering the ship or hauling lines.