Liberty Fleet of Tall Ships

What Liberty Fleet of Tall Ships does

Liberty Fleet of Tall Ships is a privately held sailing cruise operator (legal entity: Tops'L Adventures, Inc.) headquartered at Fan Pier Marina, 67 Long Wharf, Boston, MA. The company runs a fleet of two traditionally rigged wooden schooners — Liberty Star (a 67-foot gaff-rigged schooner, COI capacity 42 persons, originally built 1972 as a replica of an 1890s coastal schooner and rebuilt by Liberty Fleet in 2012) and Fame (a 70-foot Chebacco schooner, COI capacity 52 persons, a 2002–2003 Essex, MA build recreating the 1812 privateer Fame, joined the fleet in 2026) — offering 1.5- to 3-hour public and private sailing experiences on Boston Harbor from May through October. Customers include tourists, local residents, corporate groups, and private event planners (weddings, birthdays, retirements).

The core product set is structured across scheduled public sails (Boston Harbor Day Sail at $35, Sunset Sails at $62–$68, Pastries and Prosecco brunch sails at $65), premium special events (Fourth of July Fireworks at $175, USS Constitution Turnaround sails at $140, Harborfest Fireworks at $125, Sail Boston 250 sails at $68–$80), and private charters (up to 49 guests, customizable bar packages, contact for pricing). Distribution is direct-to-consumer via FareHarbor embedded on libertyfleet.com, supplemented by GetYourGuide and TripAdvisor listings and organic social (Facebook, Instagram). A Constant Contact newsletter, gift-card sales, and onboard beverage service (local craft beers, Boston-distilled spirits, $5 brunch mimosas) round out the monetization. Strategic local partnerships — Flour Bakery + Café, GrandTen Distilling, Boston By Foot Walking Tours — differentiate the brunch and educational-tour SKUs.

The business was purchased by Troy and Monica Sullivan in 2024 after approximately 30 years of operating day sails in Boston Harbor. Capacity effectively doubled in 2026 with the addition of Fame, enabling expanded parallel scheduling, broader event participation (notably the Sail Boston 250 tall ships gathering in July 2026), and a multi-vessel charter offering. The company remains privately held under Tops'L Adventures, Inc. with no disclosed institutional funding.

Name

Liberty Fleet of Tall Ships

Legal name

Tops'L Adventures, Inc.

Website

https://libertyfleet.com

Company type

Private

Founded year

1994

Operating status

Operating

Headcount range

11–50 employees

Short description

Liberty Fleet of Tall Ships, a private Boston Harbor sailing cruise operator owned by Tops'L Adventures, Inc., runs two traditionally rigged wooden schooners — Liberty Star and Fame — offering 1.5- to 3-hour public, special-event, and private charter sails from May through October for tourists, locals, corporate groups, and private event planners.

Ownership category

akta.pro rank

Product category

Maritime Tourism and Sailing Cruises

NAICS

Scenic and Sightseeing Transportation, Water (48721), Scenic and Sightseeing Transportation, Water (487210), Coastal and Great Lakes Passenger Transportation (483114)

SIC

Water Transportation (4400)

akta.pro primary industry

Luxury Yacht & Small-Ship Expedition Cruises (THAEABAF)

akta.pro secondary industries

Gulet & Traditional Wooden Yacht Cruises (THAEADAE), Crewed Yacht Charters (Luxury Crewed) (THAEAEAA), Private Yacht & Luxury Boat Charters (With Crew) (THAJALAE)

Keywords

• Sailing cruises
• Tall ship charters
• Harbor tourism
• Maritime experiences
• Boston harbor sailing

Headquarters

HQ city

Boston

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Supply Chain, Others

Revenue model

1. Public Cruise Tickets: Tickets sold for scheduled day sails, sunset sails, brunch sails, and special event cruises. Prices range from $35-$175 per person depending on cruise type and duration. Ticket sales include complimentary amenities such as pastries, coffee, and tea on specific sails.
2. Private Charters: Corporate events, teambuilding, birthday celebrations, weddings, and retirement parties. Available May through October with minimum 1.5 hours afternoons and 2 hours evenings. Can accommodate up to 49 guests plus crew. Multiple bar packages available including cash/consumption, beer/wine, or full open bar.
3. Gift Cards: Pre-purchased gift cards redeemable for any available sail or special event, including private charters. Provides advance revenue and customer acquisition.
4. Onboard Beverage Sales: Cash bar service on all cruises featuring local craft beers, Boston spirits, wine, cocktails, soda, juice, and water. Accepts cash, credit cards, and Apple Pay. Mimosas available at $5 during brunch sails.

Pricing tiers

Go-to-market motion3 records

Distribution channels4 records

Marketing channels6 records

Core offering

Liberty Fleet of Tall Ships operates scheduled public sailing cruises and private charters aboard two traditionally-rigged wooden schooners (Liberty Star and Fame) in Boston Harbor. Offerings include day sails, sunset sails, brunch sails, special event cruises, and private charters for corporate events and celebrations, departing from Fan Pier Marina May through October.

Product overview

Liberty Fleet of Tall Ships operates a portfolio of Boston Harbor sailing cruise experiences aboard two traditionally-rigged wooden schooners: the Liberty Star (67-foot gaff-rigged schooner, 42-person capacity) and Fame (70-foot Chebacco schooner, 52-person capacity). The core products include scheduled public sails — Boston Harbor Day Sail, Boston Harbor Sunset Sail, and Pastries and Prosecco brunch — along with seasonal special events such as Fourth of July fireworks cruises, USS Constitution Turnaround sails, and Harborfest fireworks cruises. The fleet also participates in the Sail Boston 250 international tall ships event in July 2026. Private charters of either vessel are available May through October for corporate events, celebrations, and teambuilding. Gift cards are sold for redemption against any cruise or charter. The company was purchased by Troy and Monica Sullivan in 2024 and has operated day sails in Boston Harbor for 30 years. Booking is handled through FareHarbor, with both vessels departing from Fan Pier Marina in Boston's Seaport District.

Differentiator

Problem solved

Functional benefit

Brands

• Liberty Star: The flagship of the fleet. A 67' sparreed length gaff-rigged schooner originally christened Rachel B. Jackson in 1972. Acquired and rebuilt by Liberty Fleet in 2012.
• Fame

Products and services

• Boston Harbor Day Sail A 1.5-hour daytime sailing cruise aboard one of the fleet's classic wooden schooners through Boston Harbor, offering scenic views of the city skyline. Priced at $35 per adult; also includes Sunday 'Pastries and Prosecco' sails and 'A Sail Through Time' narrated tours with Boston By Foot on select Sundays.
• Boston Harbor Sunset Sail

Quantifiable outcome

• 30 years of continuous operation in Boston Harbor
• +2 more outcomes

Named customers3 records

Segments5 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration3 records

Feature3 records

Partnerships

Three partnerships are on record, tiered core and minor.

• Boston By Foot Walking TourscoreStrategic or Co-development PartnerProvides knowledgeable guides for Sunday 'A Sail Through Time' educational cruises aboard Fame during midsummer. Guides narrate Boston's diverse neighborhoods and maritime history while guests enjoy spectacular harbor views. Creates differentiated educational tourism experience unavailable through standard sailing cruises.
• Reel House Oyster BarminorStrategic or Co-development PartnerLandmark restaurant adjacent to Liberty Fleet boarding location at Fan Pier Marina. Serves as visual reference point for customers navigating to the dock entrance via gangway to the right of the establishment.
• Flour Bakery + CafécoreStrategic or Co-development PartnerBoston bakery supplies freshly baked pastries for Pastries and Prosecco brunch sails. Featured as key included amenity differentiating brunch cruise from standard sails. Complimentary pastries from Flour enhance perceived value of $65 ticket price.

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Manhattan by Sail (Schooner Adirondack & Clipper City): NYC operator running traditional wooden gaff-rigged schooner Adirondack and 158-ft Clipper City tall ship for public sails, brunch cruises, and sunset sails. Nearest direct analog by vessel type, business model, and product mix.
• Bay State Cruise Company: Boston-based ferry, fast-ferry, and harbor cruise operator running scheduled services to Provincetown and themed Boston Harbor excursions. Competes for the same tourist segment via GetYourGuide and direct online booking from similar departure points.
• City Cruises Boston (Odyssey Boston): Premium dining and sightseeing cruises aboard Spirit of Boston/Odyssey vessels departing from Boston's Seaport and adjacent wharves. Directly overlaps with Liberty Fleet's premium-event and private-charter price tiers (private parties, corporate events, sightseeing).
• Mass Bay Lines: Boston Harbor day, sunset, and lighthouse cruise operator running vessels like the M/Y Bay Lady. Closest analog for general-admission scenic cruising competing head-to-head on price and duration (1.5–2 hour formats).
• Boston Harbor Cruises (City Experiences): Long Wharf-based operator running whale watches, harbor tours, sunset cruises, and ferry services from Boston Harbor on multiple vessels. Most direct competitor offering overlapping public sailing and special-event products to the same tourist and local base.

Regional players

• The Schooner Woodwind (Cruisers, LLC): 74-ft wooden schooner running 2-hour public sunset sails, private charters, and specialty cruises out of Annapolis, MD. Closely analogous sailing excursion product in a distinct geography and shoulder-season timing.
• Sail Newport (Sch. Aloft & America 2.0): Nonprofit sail training and excursion operator running public evening sails and tall-ship experiences out of Newport, RI. Comparable tall-ship excursion product and customer type, but serves a different (RI) geographic market.
• Schooner Ardelle (Yankee Fleet): 105-ft wooden gaff-rigged schooner running 2-hour public sails and private charters out of Gloucester, MA. Operates the same wooden-schooner excursion product, but in a different harbor (~30 miles from Boston).
• Clipper City Tall Ship (Sail Baltimore): Baltimore-based tall ship sailing cruise operator under the Clipper City / privateer-vessel tradition. Provides a comparable tall-ship excursion product outside the Northeast Boston market.

Emerging players

• Bay Lady Cruises / Mass Bay Lines (Boston Light & Lighthouse): Boston Harbor lighthouse and sunset cruise operator using smaller motor vessels, intersecting with Liberty Fleet on sunset-sail price points and tourist acquisition channels. Different vessel type but adjacent product offering.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key highlights7 records

Customer concentration

• Facebookfacebook.com/libertyfleetoftallships
• Instagraminstagram.com/liberty_fleet_tall_ships
• Xx.com/libertyfleet
• LinkedInlinkedin.com/company/liberty-fleet-of-tall-ships

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Liberty Fleet of Tall Ships