Tour operator
Boston Duck Tours
Amphibious sightseeing tours that cover central Boston by road before splashing into the Charles River, departing from the Prudential Center, Museum of Science and Aquarium.
Liberty Fleet of Tall Ships
Seasonal harbour sails on classic wooden schooners from Fan Pier Marina, including day, sunset and pastries-and-prosecco sailings; the fleet returns in May 2027.
At a glance
- Type
- Tall ship harbour sails
- Area
- Seaport, Boston, United States
- Official site
- libertyfleet.com
Good to know
- Classic wooden schooners
- Day and sunset sails
- Private charters
Why we recommend it
Liberty Fleet of Tall Ships, owned by TOPS'L Adventures, runs harbour sails on classic wooden schooners from Fan Pier Marina in Boston. A trip under sail is a very different experience from a motorised cruise: it is quieter and slower, and it gives you a sense of the city's long history as a seafaring port.
The most popular trip is the Boston Harbor Day Sail, which lasts about an hour and a half. The two-hour Sunset Sail is timed for the evening light over the harbour, and the two-hour Pastries and Prosecco sail is a relaxed morning or daytime option that includes tea and coffee. The company also offers special event sails and private charters, which work well for celebrations, corporate outings and family groups. Boston By Foot has partnered with the fleet for a historical sail.
The fleet operates seasonally. Its 2026 season has finished, and the company has announced that it will return to Boston in May 2027, so plan a sail for the late spring, summer or early autumn. As a general tip, book ahead for sunset sails and weekends, and check the website for exact sailing times once the new schedule is published.
As a general tip, dress in layers and bring a windproof jacket, since it is often cooler and breezier on the water than in the city, and wear flat, non-slip shoes for moving around the deck. Bring sun protection on summer afternoons. If you are prone to seasickness, a calmer harbour sail is usually gentler than open-sea trips, but it is still worth taking precautions.
Ask about accessibility when booking, since boarding a traditional sailing vessel can involve steps and uneven surfaces. Families should also check any minimum age requirements, and anyone planning a charter should contact the company well before the season opens to secure a date.
The sails suit couples, families with older children and anyone with an interest in maritime history or photography. A sail combines easily with an afternoon in the Seaport, a drink at Rooftop at The Envoy or dinner at one of the Seaport and Fort Point restaurants. To book or ask about charters, contact the company by phone or email.
Liberty Fleet of Tall Ships FAQs
Where do the sails depart?
From Fan Pier Marina in Boston.
What kinds of sails are there?
The Boston Harbor Day Sail, the Sunset Sail and the Pastries and Prosecco sail, plus private charters.
How long is a sail?
The Day Sail lasts about 1.5 hours; the Sunset and Pastries and Prosecco sails last two hours.
When does the fleet operate?
Seasonally. The fleet has announced it will return to Boston in May 2027.
What are the boats like?
Classic wooden schooners.
Can you charter a boat?
Yes. Private charters and special event sails are available.
What should you wear?
Layers, a windproof jacket and flat, non-slip shoes.
How do you contact the company?
Call 617-742-0333 or email [email protected].