Tall Ship Sailing Cruise Boston Harbor: Classic Wooden Schooners

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Free cancellationTravelers' pick

1/9

Duration1h 30m–2h

GroupUp to 49

Mobile ticketAccepted

Step aboard a wooden schooner and see Boston from the water instead of the street.

A classic tall ship cruise in Boston Harbor aboard the Liberty Star or Fame, two wooden schooners offering 90-minute to two-hour day sails with views of the city skyline and harbor landmarks. No formal tour narration—the captain and crew share stories about local history and landmarks if you ask. You can bring your own snacks or bagged lunch, though coolers and outside beverages are not permitted. Arrive 15–20 minutes before departure.

1h 30m–2h

Step-by-step itinerary

Classic sailing adventure in Boston Harbor

Board classic wooden schooner
Enjoy 90-minute sail in harbor
View Boston city skyline
Ask captain and crew questions
Relax and enjoy fresh air

The Experience

What does it feel like to sail instead of ride? You get deck space to move around, fresh air and direct sun, and the actual motion of the boat beneath your feet—something you don't get on a harbor tour that motors past the same sights. The 90-minute to two-hour sail takes you out into Boston Harbor aboard either the Liberty Star or the Fame, both classic wooden schooners built to move under sail. There's no script, no audio guide, no predetermined stops: the route depends on wind and water conditions, which means every sail is different. If you want to know what you're looking at—a landmark, a piece of history, why a building matters—you ask the captain or crew, and they'll tell you.

On Sundays at 11am, the Liberty Star runs a Pastries & Prosecco sail, a two-hour option that includes complimentary pastries and coffee from Flour Bakery plus mimosas. Beyond that, drinks are available for purchase onboard—several beers brewed in Boston, locally-distilled spirits, wine, soda, juice, and water, plus snack options. You're welcome to bring your own food or bagged lunch; just leave the coolers and outside beverages at the dock. Children must be accompanied by an adult, and infants sit on an adult's lap. Service animals are welcome. Arrive 15–20 minutes early so the crew can get you settled before departure.

If weather or unforeseen circumstances force a cancellation, you can reschedule or get a full refund. The three options—A Sail Through Time, the Fame Daysail, and the Liberty Star Daysail—let you choose which schooner and which sail time work for your schedule.

What’s included

The 90-minute to two-hour sail aboard a classic wooden schooner.
deck space and fresh air.
views of Boston Harbor and the city skyline.
access to the captain and crew for questions about local landmarks and history.
on the Pastries & Prosecco sail, complimentary pastries and coffee from Flour Bakery plus mimosas.

Good to know

Easy physical levelPets welcomePublic transport nearbyInfants must sit on laps

Operated by Liberty Fleet of Tall Ships

Is this one for you?Choose the Pastries & Prosecco sail on Sunday mornings if you want a relaxed brunch experience on the water; pick a standard daysail if you prefer flexibility on timing and want to spend your time on deck without a set menu. Either way, the lack of formal narration means you're not locked into a script—you steer the conversation with the crew toward what interests you.