What annapolis sailing school does

Annapolis Sailing School is a privately held sailing instruction business operated as Scuttlebutt, LLC from a single waterfront campus at 7001 Bembe Beach Road in Annapolis, Maryland. Founded in the early 1970s (claiming 50+ to 65+ years of operation), the school delivers American Sailing Association (ASA) accredited certification courses ranging from ASA 101 Basic Keelboat through ASA 114 Catamaran Cruising, alongside a TrySail introductory experience and a Beyond Basic Sailor advanced module. It serves adult beginners, intermediate and advanced sailors, youth ages 5-17 through the KidShip subsidiary, and corporate groups seeking team-building experiences.

The school's underlying technology asset is its specialized training fleet, headlined by the proprietary Rainbow 24 sloop designed by Sparkman & Stephens with a fixed 1,100 lb keel, cuddy cabin, and large cockpit, supplemented by Beneteau 37 cruising sailboats and Tartan 245/Caraluna sport boats. Youth instruction uses American 14.6, RS Quests, Precision 15, Hobie Getaways, Lasers, and RS Zests. Distribution combines direct-to-consumer bookings via FareHarbor, a TellTales email newsletter, Logbook blog, Instagram, YouTube educational content, and on-site sales.

Revenue is generated across multiple streams: one-time course fees ($825-$1,650 per certification), subscription-based KeelBoat Club memberships ($750-$4,000 annually with initiation fees), usage-based boat rentals ($175-$250), youth camps ($400-$650), corporate events, Bembe Beach venue rentals, and Square-powered merchandise. The KeelBoat Club three-tier structure and ASA credential ladder are the primary retention and pricing-power mechanisms.

Name

annapolis sailing school

Legal name

Scuttlebutt, LLC

Website

https://annapolissailing.com

Company type

Private

Founded year

1972

Operating status

Operating

Headcount range

11–50 employees

Short description

Annapolis Sailing School is a privately held ASA-accredited sailing school in Annapolis, Maryland, offering certification courses (ASA 101-114), youth programs (KidShip), boat rentals, a three-tier KeelBoat Club membership, corporate events, and waterfront venue rentals at Bembe Beach.

Ownership category

akta.pro rank

Product category

Sailing Instruction & Recreational Boating Services

NAICS

Marinas (713930)

SIC

Services-Educational Services (8200), Services-Membership Sports & Recreation Clubs (7997)

akta.pro primary industry

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

akta.pro secondary industry

Sailing & Water Sports Teams/Clubs (Sailing, Rowing, Surfing) (MPAKABAH)

Keywords

• Sailing instruction
• ASA certifications
• Boat rentals
• Youth sailing camps
• Sailing club membership

Headquarters

HQ city

Annapolis

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Infrastructure, Marketing or Sales, Technology or R&D

Revenue model

1. Sailing Courses: ASA-certified sailing courses from beginner (ASA 101) through advanced (ASA 114), offered as multi-day intensive programs with textbook, testing, and certification fees included.
2. KeelBoat Club Membership: Three-tier annual membership program (Social $750, Rainbow $2,100, Ultimate $4,000) with one-time initiation fees, providing discounts, unlimited rentals, racing access, and social events.
3. Sailboat Rentals: Day and half-day rentals of Rainbow 24 sloops to qualified sailors with ASA 101 certification or equivalent. Weekday full-day rentals at $175, weekend half-day rentals at $225.
4. Youth Sailing Camps: KidShip sailing camps for children ages 5-17, including Li'l Sailors (half-day $400, full-day $650), with various session options throughout the summer.
5. Corporate Events: Team-building sailing experiences, corporate regattas, and leadership retreats for businesses, with customizable half-day and full-day options.
6. Property Rentals: Event venue rentals at Bembe Beach including a lit 40'x80' pavilion tent, private sandy beach, and waterfront views for weddings, reunions, corporate events, and parties.
7. TrySails: Two-hour introduction to sailing experiences at $99 per person or $165 for two people, providing an entry-point for prospective customers to experience sailing.

Pricing tiers

Go-to-market motion3 records

Distribution channels5 records

Marketing channels8 records

Core offering

Annapolis Sailing School provides American Sailing Association (ASA)-certified sailing instruction across progressive levels from ASA 101 Basic Keelboat through ASA 114 Catamaran Cruising, using a proprietary fleet that includes Sparkman & Stephens-designed Rainbow 24 sloops, Beneteau 37 cruisers, and Tartan 245 sport boats. The school also runs the KeelBoat Club annual membership program, KidShip youth sailing camps, day and half-day Rainbow 24 sailboat rentals for certified sailors, corporate team-building regattas, and Bembe Beach event-venue rentals.

Product overview

Annapolis Sailing School offers a comprehensive sailing education platform centered on American Sailing Association (ASA) certification courses. The core offering consists of progressive ASA certifications (ASA 101, 102, 103, 104, 114) ranging from beginner to bareboat cruising levels, supplemented by advanced courses like Beyond Basic Sailor (spinnaker work) and TrySails (introductory experiences). The school operates a membership-based KeelBoat Club with tiered benefits including unlimited boat rentals and racing access. Additional revenue streams include recreation sailing (boat rentals, evening charters), youth sailing (KidShip program), corporate events, property venue rentals (Bembe Beach Events), yoga classes, and retail merchandise. The school utilizes its own fleet including Rainbow 24 daysailers, Beneteau 37 cruising boats, Tartan 245/Caraluna sport boats, and various dinghies (RS Quest, Hobie Getaway, American 14.6, Lasers, RS Zests).

Differentiator

Problem solved

Functional benefit

Brands

• KidShip: Youth sailing camp program for children ages 5-17, offering Li'l Sailors (ages 5-7), half-day and full-day camps, and various youth sailing instruction programs.
• KeelBoat Club
• Bembe Beach Events

Products and services

• ASA 101 Basic Keelboat Sailing Course Entry-level ASA-certified sailing course teaching terminology, theory, points of sail, rigging, winch techniques, tacking, jibing, steering, and basic rules of the road. Available as 3-day weekday ($825), 3-day weekend ($875), or part of the 5-day Complete Sailor course. Includes textbook, ASA testing fees, logbook, and 3-month ASA trial membership.
• ASA 101 Complete Sailor Course Comprehensive 5-day beginner sailing course combining ASA 101 and ASA 102 Basic Keelboat certifications. Covers introduction to spinnakers, docking under sail, and advanced sail trim on Rainbow 24s and Tartan 245s. Includes textbook, testing fees, logbook, and 3-month ASA trial membership.
• ASA 101 & 103 Advanced Sailor Course Accelerated 5-day combined course covering both ASA 101 and ASA 103 certifications at $1,650/person. Combines Rainbow 24 training with Beneteau 37 cruising sailboat experience. Includes textbooks, testing, certification fees, and 3-month ASA trial membership.
• ASA 103 Basic Coastal Cruising Course Three-day intermediate sailing course at $1,150/person for ASA 101 graduates. Covers cruising sailboat terminology, auxiliary engine operation, docking, intermediate sail trim, navigation rules, anchoring, and weather interpretation on Beneteau 37s. Includes Basic Coastal Cruising textbook, ASA 103 testing fees, and certification.
• ASA 104 Bareboat Cruising Course Live-aboard 3-day, 2-night certification course at $1,450/person on Beneteau 37s preparing students for bareboat chartering. Includes onboard accommodations with provided linens and provisions, Bareboat Cruising textbook, testing, and ASA 104 certification fees.
• ASA 114 Catamaran Cruising Course Advanced catamaran certification course at $1,045/person covering differences between mono-hull and catamaran operation, docking, anchoring, and systems. Prerequisites: ASA 101, 103, and 104. Requires minimum 2 students. (Listed as currently unavailable as of 2023.)
• Beyond Basic Sailor Advanced Course Two-day advanced course at $600/person covering spinnaker handling, advanced sail trim, teamwork, weather planning, anchoring under sail, and reefing. Taught on Caraluna 245 by Tartan sport boats. Ages 16+.
• TrySail Introductory Sailing Experience Two-hour introduction to sailing aboard Rainbow 24s at $99 per person or $165 for two people. Covers basic boat parts, steering, tacking, and jibing. Offered May–August weekends 10am–12pm or 2pm–4pm. Minimum 2 people, maximum 5 per boat. Ages 10+.
• Private Sailing Instruction Personalized one-on-one sailing instruction at the student's individual pace. Includes 2-hour private instruction sessions, also available as a benefit to KeelBoat Club members.
• Powerboat Operation Courses Powerboat operation instruction offered separately from sailing courses under the Annapolis Powerboat School brand.
• KidShip Youth Sailing Camps Youth sailing program for children ages 5–17 operated by wholly owned subsidiary KidShip Sailing School. Includes Li'l Sailors (ages 5–7, half-day $400 / full-day $650), older youth camps, Family TrySails, and CIT (Counselor-in-Training) program. Uses American 14.6 training boats and other age-appropriate vessels.
• KeelBoat Club Membership Three-tier annual membership program — Social ($750/yr), Rainbow ($2,100/yr), Ultimate ($4,000/yr) — each with a one-time initiation fee. Members receive course discounts (10–20%), unlimited or discounted Rainbow 24 rentals, Sunday and Monday night racing, social events, seminars, Dinghy access, and clubhouse amenities (SailShed). Ultimate tier adds Newport 30 and Sabre 34 access plus singlehanded Rainbow endorsement eligibility.
• Rainbow 24 Sailboat Rentals Day and half-day rentals of Rainbow 24 sloops to qualified sailors holding ASA 101 certification or equivalent. Weekday full-day rentals $175 (9am–4pm); weekend half-day rentals $225 (9am–12:30pm or 1pm–4:30pm).
• Evening Sail Charters Sunset sailing experiences aboard Rainbow 24 sloops departing from Bembe Beach on the Chesapeake Bay.
• Corporate Sailing Events and Regattas Team-building and corporate events including half-day and full-day sailing experiences, corporate regattas, client entertainment, and leadership retreats on Chesapeake Bay. Custom quote-based pricing.
• Bembe Beach Event Venue Rentals Event venue rentals at Bembe Beach featuring a lit 40'x80' pavilion tent, private sandy beach, and waterfront views of the Severn River and Chesapeake Bay. Hosts weddings, reunions, corporate events, and parties.
• Outdoor Yoga Classes Outdoor yoga sessions offered April through October on a floating platform at Bembe Beach, in partnership with Blue Lotus Yoga Studio and Groundswell Yoga.
• Sailing Gift Vouchers Gift certificates available for sailing courses and experiences, valid for 5 years from purchase.
• Sailing Flotilla Trips Group multi-day sailing flotilla trips, including the 2027 Flotilla now open for booking, providing immersive multi-vessel cruising experiences for sailing enthusiasts.
• Annapolis Sailing School Merchandise Shop Online merchandise store selling branded apparel and accessories via the Square e-commerce platform.

Named customers4 records

Segments6 records

Ideal customer profiles7 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration4 records

Feature3 records

Partnerships

One partnership is on record.

• FareHarborcoreTechnology or IntegrationOnline booking platform integrated into the school's website for real-time availability and reservations for courses, TrySails, and rentals.

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Offshore Sailing School: Founded by Steve Colgate, Offshore Sailing School is a long-established ASA-accredited sailing school offering beginner-to-bareboat certification courses at multiple U.S. and Caribbean locations. Directly comparable to Annapolis Sailing School in curriculum (ASA ladder), target customer (adult learners seeking certification), and delivery model (multi-day hands-on courses on fleet of training vessels).
• J/World Annapolis Performance Sailing School: J/World Annapolis is a sailing school based in the same Annapolis market offering performance-oriented sailing instruction with a focus on racing skills. Directly comparable as a co-located, ASA-aligned sailing school competing for the same Mid-Atlantic adult beginner-to-advanced customer base.

Broad incumbents

• US Sailing Association: US Sailing is the national governing body for the sport of sailing in the United States, providing accreditation standards, instructor certification, and sailing programs. Comparable as the broader umbrella organization whose certification ecosystem Annapolis Sailing School operates within; also offers its own instruction programs competing for the same adult sailor market.
• Sunsail: Sunsail is a global bareboat yacht charter company operating fleets in the Caribbean, Mediterranean, and other cruising destinations. Comparable because graduates of ASA 104 Bareboat Cruising (Annapolis Sailing School's top course) frequently feed into Sunsail's charter customer base, making it a downstream channel partner as well as a destination competitor for advanced sailors.
• Dream Yacht Charter: Dream Yacht Charter is one of the world's largest bareboat and crewed yacht charter operators with destinations worldwide. Comparable to Annapolis Sailing School in that it represents the downstream opportunity for ASA-certified sailors and competes for the same aspirational recreational sailing customer.

Others

• SailTime: SailTime is a fractional sailboat ownership and membership program providing access to a fleet of sailing yachts in multiple U.S. locations. Comparable as an adjacent business model targeting sailing-interested consumers seeking ongoing boat access without full ownership — overlapping with the KeelBoat Club's value proposition.
• Freedom Boat Club: Freedom Boat Club is a membership-based recreational boat club operating franchise locations across the U.S. with a model similar in concept to Annapolis Sailing School's KeelBoat Club (annual membership for boat access). Comparable because it competes for the same recurring-revenue recreational boater customer seeking boat access without ownership.
• Annapolis Yacht Club: Annapolis Yacht Club is a premier private sailing and social club located on the Chesapeake Bay in the same market as Annapolis Sailing School. Comparable as an adjacent sailing organization — it competes for club-membership dollars and regatta participation while also being a corporate events partner (per the school's customer list).
• SpinSheet Sailing Magazine: SpinSheet is a Chesapeake Bay-based sailing publication covering regional sailing news, racing, and cruising. Comparable as an adjacent ecosystem participant — not a direct competitor, but a media channel that amplifies the school's community events (Sunday/Monday night racing, flotillas) and influences the Mid-Atlantic sailing consumer base.

Emerging players

• NauticEd: NauticEd is an online sailing education platform offering theoretical sailing courses, certification, and bareboat charter readiness preparation. Comparable as an alternative delivery model addressing the same certification pathway (theoretical knowledge portion of sailing instruction) at lower cost and with greater convenience — a partial substitute rather than full direct competitor.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks5 records

Key highlights7 records

Customer concentration

• Instagraminstagram.com/annapolissailingschool
• LinkedInlinkedin.com/company/annapolis-sailing-school

Compliance1 record

Revenue estimate

Valuation estimate

Number of profiles

Subsidiaries1 record

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 annapolis sailing school