
easy
1.5–2 hours
Suitable for most fitness levels; you should be able to step up a short gangway and stand or sit for the duration.
Step aboard the schooner Adirondack for a 1.5 or 2-hour sail from Rowes Wharf and see Boston from the water—lighthouses, Fort Independence, Spectacle Island and a skyline that loosens its grip as the harbor takes over.
The schooner slips free of Rowes Wharf with a soft sigh of rigging and the city releases you. Glass towers of the Seaport recede into a low-brick shoreline punctuated by the squat mass of Fort Independence on Castle Island. Salt air moves through the rigging like a living thing, and within minutes downtown Boston is a backdrop to gulls, lighthouses and a chain of harbor islands that have shaped New England’s maritime story.

Even summer afternoons feel cooler on the water—bring a windproof layer and a hat to block spray.
Picnics are permitted and make the trip more relaxed—use a soft cooler and no glass.
Drinks are card-only aboard the boat—have a card ready to avoid last-minute scrambling.
Plan to be at Rowes Wharf 15–30 minutes before departure; boarding closes five minutes prior.
The harbor islands and piers were central to Boston’s shipbuilding and trade; Fort Independence on Castle Island has fortified the harbor since colonial times.
The Boston Harbor Islands National Recreation Area and long-term cleanup projects have restored water quality and wildlife habitat, but visitors should avoid disturbing nesting birds and pack out all trash.
Blocks chill and spray encountered once you clear the pier.
spring specific
Helps reduce glare off the water and keeps sunglasses from blowing overboard.
summer specific
Useful for spotting seals, birds, and distant lighthouses around the islands.
fall specific
Allowed onboard and makes for a leisurely snack while sailing.
summer specific