What Schooner Woodwind does

Schooner Woodwind is a family-owned sailing tour operator based in Annapolis, Maryland, that runs public and private sailing experiences on the Chesapeake Bay from two identical 74-foot wooden staysail schooners — Woodwind (1993) and Woodwind II (1998). The vessels were custom-designed by John Scarano and built by Scarano Boat Builders using Port Orford cedar laminated frames, Alaskan cedar beams, Douglas fir decking, and fiberglass-sheathed wood/epoxy construction, displacing 52,000 lbs with a 7-foot draft and carrying 1,800 sq. ft. of sail area each. The company is USCG-certified for 48 day passengers (voluntarily capped at 30 for public cruises) and operates seasonally from mid-April through the end of October, departing up to four times daily from the Annapolis Waterfront Hotel.

The business sells tickets across a distributed channel mix — on-site dock ticket office, online booking, and phone reservations — and earns from public 2-hour cruises, sunset and specialty sails (wine tastings, beer tastings, lighthouse tours, brunch/dinner cruises), private charters (weddings, bachelorette parties, corporate events, team-building match racing between the two identical boats), educational student and scout programs, multi-day passages, branded merchandise, gift certificates, and 360 feet of managed transient dockage at the Annapolis Waterfront Hotel. Pricing is unit-based and varies by experience; contracts for private charters typically bundle gratuities and taxes. The customer base is highly fragmented across tourists, locals, corporate groups, students, scouts, and celebration hosts, with no individual customer representing material revenue.

The company has operated continuously for 30 years (founded 1993 by Captain Ken and Ellen Kaye, former Connecticut public school teachers; daughter Captain Jennifer Kaye joined in 1996), accumulating eight TRIFECTA wins in the Great Chesapeake Bay Schooner Race, a 4.8 Google rating across thousands of reviews, TripAdvisor Travelers' Choice recognition, and a feature in the 2005 film Wedding Crashers. In October 2025, 59° North Sailing acquired the vessels and operations, transitioning the business to focus on select passages and races while continuing the family legacy on the Bay.

Name

Schooner Woodwind

Legal name

Running Free, LLC

Website

https://schoonerwoodwind.com

Company type

Private

Founded year

1993

Operating status

Operating

Headcount range

11–50 employees

Short description

Schooner Woodwind is a family-owned Annapolis, Maryland sailing operator that runs public 2-hour cruises, private charters, specialty themed sails, and educational programs from two identical 74-foot wooden staysail schooners on the Chesapeake Bay from April through October.

Ownership category

akta.pro rank

Product category

Recreational Sailing Tours

NAICS

Scenic and Sightseeing Transportation, Water (48721)

SIC

Water Transportation (4400)

akta.pro primary industry

Sailing Experiences (Lessons, Regattas, Day Sails) (THAJAJAG)

akta.pro secondary industry

Luxury Sailing Cruises (Windjammers & Tall Ships) (THAEADAB)

Keywords

• Sailing cruises
• Private charters
• Recreational boating
• Chesapeake bay tours
• Team building sails

Headquarters

HQ city

Annapolis

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Infrastructure, Others

Revenue model

1. Public Sailing Cruises: Daily 2-hour sailing excursions on Chesapeake Bay departing up to 4 times daily from April through October. Tickets sold online, by phone, and at dock office.
2. Private Charters: Full-boat private charters for corporate events, bachelorette parties, birthdays, weddings, and team building. Includes custom catering options through exclusive caterer.
3. Specialty Cruises: Premium themed cruises including sunset sails, wine/beer tasting, lighthouse cruises, brunch cruises, and holiday fireworks cruises with higher ticket pricing.
4. Merchandise Sales: Ship's Store selling branded merchandise including t-shirts, hooded sweatshirts, hats, patches, postcards, and koozies. Available at dock office and online.
5. Gift Certificates: Print-at-home or email gift certificates available in various denominations for gift giving.
6. Dock Space Management: Manages 360 feet of wharf side dock space for transient dockage at Annapolis Waterfront Hotel.

Pricing tiers

Go-to-market motion2 records

Distribution channels4 records

Marketing channels8 records

Core offering

Schooner Woodwind sells recreational sailing experiences on two 74-foot wooden staysail schooners (Woodwind and Woodwind II) operating daily public 2-hour cruises, sunset sails, and specialty themed cruises (wine/beer tasting, lighthouse, brunch, dinner) from the Annapolis Waterfront Hotel on the Chesapeake Bay. It also offers full-boat private charters for weddings, corporate team building, bachelorette parties, and celebrations, plus student/scout educational programs, schooner racing, and multi-day sailing passages. Revenue is complemented by branded merchandise and gift certificates sold through the dock and online Ship's Store.

Product overview

Schooner Woodwind operates two identical 74-foot wooden two-masted staysail schooners (Woodwind and Woodwind II) for sailing experiences on the Chesapeake Bay from Annapolis, Maryland. The core offering consists of daily public 2-hour sailing cruises and sunset sails, supplemented by private charters for corporate events, team building, and celebrations. Specialty offerings include themed cruises featuring wine tastings, beer tastings, dinner service, brunch, and lighthouse tours. The company also offers student and scout educational programs, schooner racing participation (including Wednesday night races and the Great Chesapeake Bay Schooner Race), and multi-day cruise options. Merchandise and gift certificates are available as ancillary products.

Differentiator

Problem solved

Functional benefit

Brands

• Woodwind II: The second identical 74-foot schooner, launched June 10, 1998. Used in the movie 'The Wedding Crashers' and operates alongside Woodwind for public and private sailing cruises.

Quantifiable outcome

• Less than 1% seasickness rate among passengers due to heavy ballasted keel and protected waters
• +2 more outcomes

Named customers6 records

Segments5 records

Ideal customer profiles5 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

Six partnerships are on record, tiered core and minor.

• 59° North SailingcoreStrategic or Co-development Partner · 1 October 202559° North Sailing acquired Woodwind and Woodwind II in October 2025 and now offers select passages and races aboard the schooners. The partnership continues the family sailing legacy with professional sailing passages including the Great Chesapeake Bay Schooner Race and multi-day trips to Norfolk.
• Scarano Boat BuildersminorOthersAlbany, New York boat builder that custom designed and constructed both Woodwind (1993) and Woodwind II (1998). Designer John Scarano created the staysail schooner design specifically for Annapolis day charter operations.
• Annapolis Waterfront Hotel (Marriott)coreStrategic or Co-development PartnerLocation partner where Woodwind vessels are docked and cruises depart from. Schooner Woodwind manages 360 feet of wharf side dock space for transient dockage on behalf of the hotel. Hotel features Pusser's Caribbean Grille and provides guest referrals.
• Pusser's Caribbean Grille/Pusser's Dock BarminorGTM or Marketing PartnerOn-site restaurant and bar at Annapolis Waterfront Hotel where guests can wait before cruises. Reference in employment materials as nearby amenity for staff.
• Chesapeake Chapter of the U.S. Lighthouse SocietyminorStrategic or Co-development PartnerGuest lecturers from this organization accompany Lighthouse Cruises to provide historical and educational commentary about Chesapeake Bay lighthouses.
• Weems & PlathminorOthersAnnapolis-based company that gifted a Tamaya sextant to 59° North for celestial navigation aboard their vessels.

Scale indicators11 records

Recent moves7 records

Expansion highlights5 records

Direct peers

• Woodwind's Direct Competitor: H.M. Krentz / Schooner Wilbert Lee: A traditional wooden schooner offering public and private cruises in the Chesapeake Bay / DC area. Competes for the same day-sail and special-event cruise customers seeking an authentic wooden sailing experience.
• Bay Lady Cruises: Annapolis-based sailing tour offering public daytime and sunset cruises on the Chesapeake Bay. Direct competitor with similar vessel type, sailing experience, and tourist customer base.
• Mystic Whaler Cruises: Classic tall-ship schooner operator running day sails, sunset cruises, and private charters in New England waters. Comparable vessel type (wooden passenger schooner), product mix, and customer base to Schooner Woodwind, though on a different coast.
• Catherine Marie Charter Fishing: Annapolis-based charter operator offering private boat charters on the Chesapeake Bay. Competes for the same private-charter customer segment (corporate, events, groups) in the same geography.
• Schooner Adirondac III: Annapolis-based sailing tour operator running public 2-hour cruises, specialty cruises (lunch, sunset), and private charters on a wooden schooner. Direct day-sail competitor with overlapping product set and the same Chesapeake Bay footprint.
• Sail Annapolis: Annapolis sailing tour and charter operator providing public sails, private charters, and sailing lessons. Competes for both the tourist sailing experience and the private event market on the Chesapeake Bay.

Regional players

• Annapolis Sailing School: Long-established Annapolis sailing school offering ASA-certified courses and charter services. Overlaps in Chesapeake Bay sailing experiences and shares the same geography, but its core business is sailing instruction rather than passenger cruises.
• Severn River Sailing Association: Annapolis-based sailing organization offering sailing lessons, junior programs, and racing. Adjacent to Schooner Woodwind's student/scout sailing programs and racing activities in the same geographic market.

Broad incumbents

• City Experiences (City Cruises): National harbor cruise and water-tour operator (formerly Hornblower) running dining cruises, sightseeing tours, and private charters across multiple U.S. cities. Overlaps with Schooner Woodwind's specialty cruise and corporate event offerings but at much larger scale and in a different (motorized) vessel class.

Others

• 59° North Sailing: Acquired Schooner Woodwind in October 2025; operates multi-day sailing passages and races on the Chesapeake Bay. Now part of the same corporate family but represents the higher-end passage product line vs. Schooner Woodwind's day-sail core.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/annapsailing
• YouTubeyoutube.com/channel/UCVPpAcg5n5zXm0nsy9X0OSg
• Facebookfacebook.com/SchoonerWoodwind
• Instagraminstagram.com/schoonerwoodwind
• LinkedInlinkedin.com/company/schooner-woodwind

Revenue estimate

Valuation estimate

Number of profiles

Profiles3 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 Schooner Woodwind