Sailing Private Charters on the Liberty Star, Boston

Read the full experience

Boston Harbor offers a unique blend of urban history and maritime tradition, best experienced from the deck of the Liberty Star. This beautifully maintained 67-foot wooden schooner, crafted in the style of the 1890s, provides visitors with an immersive sailing experience that highlights Boston’s rich nautical heritage. Operating as a private charter vessel, the Liberty Star can host up to 39 guests who are invited to participate in the authentic experience of raising sails or simply relax and enjoy panoramic views of the city’s waterfront and historic landmarks. The schooner itself is a remarkable example of classic shipbuilding, featuring traditional rigging and timber construction that evoke the golden age of sailing. Cruising Boston Harbor aboard the Liberty Star reveals water views framed by iconic sites such as the Boston Skyline, Charlestown Navy Yard, and nearby islands that tell stories of maritime innovation and early American history. This hands-on experience is perfect for groups seeking a private event with a nautical twist—be it corporate gatherings, celebrations, or educational trips. What sets Liberty Star apart in Boston’s outdoor recreation scene is its dedication to authentic sail training on a historic vessel. Guests don’t just watch from the sidelines; they can engage with the crew and learn elements of traditional sailing, fostering a deeper connection with Boston’s maritime roots. This is an adventure that combines heritage, education, and breathtaking scenery in one unique package. Whether you’re a history buff, sailing enthusiast, or simply looking for an unforgettable way to experience Boston’s waterfront, the Liberty Star private charters offer an unmatched journey on the water. It stands as a stellar example of how Boston preserves and celebrates its seafaring legacy through interactive adventure.

Trip highlights

Difficulty

moderate.

Duration

2–4 hours.

Fitness level

Moderate fitness recommended to participate in sail handling; relaxed options available for non-active guests.

Frequently asked questions

Can guests actively participate in sailing?

Yes, guests are encouraged to help raise and handle sails under crew supervision.

What is the typical duration of a private charter?

Most charters last between two and four hours, customizable to your group’s preferences.

Is the Liberty Star wheelchair accessible?

The schooner’s traditional design limits accessibility; please inquire about accommodations.

Are refreshments provided on board?

Food and drink policies vary; many charters allow you to bring your own or arrange catering.

What should I wear for a charter on the Liberty Star?

Wear layers with wind- and water-resistant outerwear, plus flat, non-marking footwear.

How far in advance should I book a charter?

We recommend booking at least a month in advance to secure preferred dates, especially in peak season.

Local insights

Wildlife

Harbor seals often spotted near islands
Ospreys nesting on harbor piers

History

Boston Harbor has been a center of American maritime trade since the 17th century, with schooners like the Liberty Star echoing this rich heritage.

Conservation

The Liberty Star promotes sustainable boating practices to protect the delicate marine ecosystems of Boston Harbor.

About Liberty Fleet of Tall Ships

Liberty Fleet of Tall Ships operates from Boston, MA, offering authentic schooner sails aboard the 67’ wooden Liberty Star. The company presents a variety of public and private experiences on Boston Harbor, including the Boston Harbor Day Sail, Boston Harbor Sunset Sail, Pastries and Prosecco, 4th of July Fireworks cruise, the Annual USS Constitution Turnaround Sail, and private charters. Each public cruise departs from Fan Pier Marina or other Boston Harbor launch points and invites up to 39 guests to enjoy skyline views, drinks, and light snacks while sailing aboard a classic vessel built to evoke 1890s craftsmanship. On special-event sails, Liberty Fleet provides themed amenities: the 4th of July Fireworks cruise features a fully stocked bar and a 2.5-hour itinerary; the USS Constitution Turnaround Sail includes a continental breakfast and a chance to witness the historic ship’s 21-gun salute; Pastries and Prosecco offers complimentary pastries and a drink menu with $5 mimosas. The Boston Harbor Day Sail and Sunset Sail focus on scenic harbor views, knowledgeable crew interaction, and a relaxed atmosphere. Private charters aboard the Liberty Star accommodate groups up to 39 and allow guests to participate in raising the sails or simply relax while taking in historic Boston. With clearly described itineraries, onboard provisions, and a professional crew, Liberty Fleet of Tall Ships provides transparent, bookable maritime experiences rooted in Boston’s harbor history. Reservations and trip details are listed online for each scheduled sail, including durations, amenities, ticketing, clear departure times, boarding information, and accessibility notes available.

Base locationBoston, Massachusetts

Tours offered6+

Specialty

Adventure tips

Book in advance for prime datesLiberty Star charters fill quickly during summer weekends and holidays; early reservations secure your preferred slot.

Dress for changing weatherBring layers as conditions on the water can shift quickly, even on sunny days.

Wear non-marking, flat shoesProtect the vessel’s deck and ensure safe footing by opting for appropriate footwear.

Arrive early for boardingPlan to arrive 15 minutes before your charter start time to meet the crew and get safety instructions.

Recommended gear

Windbreaker jacket: Keeps you warm and dry against cool spring breezes on Boston Harbor.
Sunscreen: Protects against sun exposure during the open water daytime hours.
Hat with a brim: Shields your face from sun glare while sailing.
Comfortable layered clothing: Allows quick adjustment to temperature changes common in coastal fall weather.