Business Details
32 Years
experience
Boston Harbor Sailing Cruises Aboard the Liberty Star
Liberty Fleet Of Tall Ships has been operating day sails in Boston Harbor for 30 years, offering immersive maritime experiences aboard historic tall ships. Founded in 1994, the company was acquired in 2024 by Troy and Monica Sullivan, who bring decades of combined sailing expertise from their extensive voyages across the Atlantic, Pacific, Great Lakes, and Caribbean. The Liberty Star, now the flagship vessel, provides guests with opportunities to engage with the crew and experience the golden age of sailing.The Sullivans, who met aboard a schooner in 2005, are committed to preserving maritime heritage while introducing new generations to the joys of tall-ship sailing through family-friendly adventures and educational programs.
Services
Day Sails
Sunset Cruises
Fireworks Voyages
Historic Tours
Private Charters
Educational Programs
Details
- Year established: 1994
Highlights and features
- 30 years of Boston Harbor sailing expertise
- Family-owned operation with professional mariners
- Authentic tall ship crew participation experiences
- Multi-generational family sailing adventures
- Strategic Seaport District location with easy access
What people say
Scenic views
Historic experience
Knowledgeable crew
Family-friendly
Unique adventure
Services
Day Sail
Enjoy a 1.5-hour Boston Harbor adventure aboard the Liberty Star schooner. Experience historic sailing with optional crew participation. Ideal for families and first-time visitors seeking scenic views of the Boston skyline and waterfront landmarks.
Sunset Sail
Two-hour twilight sailing experience showcasing Boston's waterfront at dusk. Combines historic sailing with panoramic views of the city's illuminated skyline. Recommended for romantic outings and special celebrations.
Pastries and Prosecco
Weekend 2-hour sailing featuring gourmet pastries and champagne service. Combines Boston Harbor sightseeing with luxury amenities. Includes tea, coffee, and premium sparkling wine with harbor vistas.
Fireworks Cruises
Fourth of July and Harborfest fireworks viewing voyages. Offers premium vantage points for Boston's major fireworks displays. Includes reserved seating and beverage service during special event nights.
USS Constitution Sail
Specialty sail past the USS Constitution with educational narration about Boston's naval history. 1.5-hour voyage includes close views of 'Old Ironsides' and harbor landmarks.
People
Troy Sullivan
Co-Owner & Captain
Professional mariner with 30+ years sailing experience across four oceans. Former crew member of international tall ship expeditions. Purchased Liberty Fleet in 2024 to realize his lifelong dream of operating a Boston-based sailing business.
Monica Sullivan
Co-Owner & Operations Director
Experienced maritime professional with expertise in nautical tourism operations. Met Troy aboard a Connecticut schooner in 2005. Oversees guest experiences and educational programming for Liberty Fleet's Boston Harbor voyages.
Questions
What sailing experiences are available in Boston Harbor?
Liberty Fleet offers day sails, sunset cruises, themed voyages, and special event fireworks cruises aboard the Liberty Star schooner.
Can guests participate in sailing activities?
Yes, guests can temporarily join the crew to handle sails and lines under professional supervision during most voyages.
What is included with the Pastries and Prosecco cruise?
This weekend cruise includes gourmet pastries, champagne, tea, and coffee with 2 hours of Boston Harbor sailing.
How to access the boarding dock?
Boarding is at Fan Pier Marina's outer dock via the gangway right of Reel House Oyster Bar in Boston's Seaport District.
What transportation options exist for the marina?
The marina is 20 minutes from South Station, 5 minutes from Courthouse MBTA stop, and accessible via Harbor Walk pedestrian routes.
Are private charters available?
Yes, the Liberty Star can be chartered for private events, corporate outings, and special celebrations in Boston Harbor.
