The Sailing Academy
The Sailing Academy is a family-owned ASA-certified sailing school in Tracys Landing, MD, offering beginner-to-offshore certification courses, bareboat charters, a subscription Sailboat Club, and family sailing vacations on Chesapeake Bay and in the Bahamas for adult learners, families, and youth ages 5-15.
- Company typePrivate
- Founded2002
- HeadquartersTracys Landing, United States
- Headcount11–50
- GTM typeB2C
- OfferingServices
What The Sailing Academy does
The Sailing Academy is a private, family-owned sailing instruction and water sports education business founded in 2002 and based at Herrington Harbour Marina in Tracys Landing, Maryland, the closest sailing school to the Washington DC Beltway. The company delivers American Sailing Association (ASA) certification courses ranging from beginner (Sailing Basics, ASA 101 Basic Keelboat Sailing) through advanced coastal and offshore levels (ASA 103, 104, 105, 106, 114 Catamaran Cruising), plus DELMARVA Circumnavigation and Bay-to-Bahamas/Bay-to-Bermuda offshore passages. It serves adult learners, families, and children ages 5-15, with all instruction conducted aboard a premium fleet of VIKO yachts (26-35 ft) equipped with wheel steering, inboard engines, roller furling, chart plotters, GPS, and autopilot.
The core technology platform is a fleet of premium cruising yachts (VIKO 26/30/35, Catalina 270, Beneteau 331, Sabre 425, Jeanneau 36), each with modern amenities, that the company states is the only such fleet offered by a sailing school on Chesapeake Bay. The supporting infrastructure includes a Wix-hosted website with Peek scheduling integration, sailingcamp.org for youth camp enrollment, and content distribution across Instagram, TikTok, Facebook, X, and YouTube.
The business operates five interlocking revenue streams: ASA course fees (professional services), bareboat yacht charters on a unit-pricing basis ($550-$1,285/day), a Sailboat Club subscription membership (7 half-day sails per month, May 1 to November 1), all-inclusive family sailing vacations in Abaco, Bahamas ($4,900-$9,500) and Chesapeake Bay, and youth sailing camps delivered through a partnership with Planet Hope Land and Sea. Pricing is fully disclosed on the website, all charters carry an 11% Maryland tax plus a $150 cleaning fee, and a 50% non-refundable deposit is required. Distribution is direct-to-consumer via website booking, supplemented by phone/email and an external channel for youth camps. The company has trained 30,000+ students over its history and is led by founder Captain Jeff Bowen, with three USCG-licensed captains and six sailing instructors in the Bowen family and extended team.
The Sailing Academy firmographics
Firmographics- Name
- The Sailing Academy
- Legal name
- The Sailing Academy
- Website
- https://thesailingacademy.com
- Company type
- Private
- Founded year
- 2002
- Operating status
- Operating
- Headcount range
- 11–50 employees
- Short description
- The Sailing Academy is a family-owned ASA-certified sailing school in Tracys Landing, MD, offering beginner-to-offshore certification courses, bareboat charters, a subscription Sailboat Club, and family sailing vacations on Chesapeake Bay and in the Bahamas for adult learners, families, and youth ages 5-15.
- Ownership category
- akta.pro rank
The Sailing Academy industry classification
Industry- Product category
- Maritime Sailing Instruction
- NAICS
- Marinas (713930)
- SIC
- Services-Educational Services (8200), Services-Miscellaneous Amusement & Recreation (7990)
- akta.pro primary industry
- Sailing Experiences (Lessons, Regattas, Day Sails) (THAJAJAG)
- akta.pro secondary industries
- Navigation, Seamanship & Offshore Operations (EDAOANAE), Luxury Sailing Cruises (Windjammers & Tall Ships) (THAEADAB), Cruise Yacht Charters (Private Crewed) (THAEADAG), Educational Cruises & Shipboard Learning Programs (THAKAGAM)
Keywords
Where The Sailing Academy is headquartered
LocationHeadquarters
- HQ city
- Tracys Landing
- HQ country
- United States
- HQ region
- North America
Offices4 records
Markets served
The Sailing Academy business model
Business model- GTM type
- B2C
- Offering type
- Services
- Cost components
- Personnel, Operations, Infrastructure, Marketing or Sales, Others
Revenue model
- Sailing Courses and Certifications: ASA-certified sailing courses from beginner to advanced levels including Sailing Basics, ASA 101-106, coastal navigation, catamaran cruising, and offshore passages. Revenue generated from course fees which include instruction, materials, boats, and certification.
- Bareboat Yacht Charters: Day-sail and multi-day bareboat charters on Chesapeake Bay. Charters include VIKO 26, VIKO 30, VIKO 35, Catalina 270, Beneteau 331, Sabre 425, and Jeanneau 36. First-time charters require checkout sail with captain.
- Sailboat Club Membership: Monthly membership providing guaranteed sailing access from May 1 through November 1. Members receive 7 half-day sails per month (5 weekday, 2 weekend) on shared vessels. Requires sailing resume submission and approval.
- Sailing Vacations: Family sailing adventures in Abaco, Bahamas (February-April) and Chesapeake Bay (May-October). Includes 6-day all-inclusive packages with captain, lodging aboard for up to 6 guests, breakfasts, and adventure activities.
- Youth Sailing Camps: Summer sailing camps through Planet Hope Land and Sea partnership. Programs include Mini Mariners (ages 5-7), Youth Sailing (ages 8-13), and CAPS leadership program (ages 13-15) at Herrington Harbour South.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Other | Multi-year contract | Abaco Bahamas Sailing Vacation - 6 day family adventure |
| Other | Multi-year contract | Chesapeake Bay Weekend Adventure |
| Other | Multi-year contract | Chesapeake Bay 5-Day Adventure |
| Unit Pricing | Pay-as-you-go | VIKO 35 Day Sail |
| Unit Pricing | Pay-as-you-go | VIKO 26 Day Sail |
| Unit Pricing | Pay-as-you-go | Catalina 270 Day Sail |
| Unit Pricing | Pay-as-you-go | Beneteau 331 Day Sail |
| Unit Pricing | Pay-as-you-go | VIKO 30 Day Sail |
| Unit Pricing | Pay-as-you-go | Sabre 425 Multi-Day |
| Unit Pricing | Pay-as-you-go | Jeanneau 36 Multi-Day |
| Other | Pay-as-you-go | Sailing Basics - 2-Day Beginner Course |
| Other | Pay-as-you-go | ASA 101 Basic Keelboat Sailing |
| Other | Pay-as-you-go | Basics + ASA 101 Combo - 4-Day Course |
| Other | Pay-as-you-go | ASA 103/104 Combo - 5-Day Coastal and Bareboat Cruising |
| Other | Multi-year contract | Bahamas ASA 103/104 Combo Course |
| Other | Multi-year contract | Bahamas ASA 101 Course |
Go-to-market motion1 record
Distribution channels3 records
Marketing channels9 records
The Sailing Academy product offering
Product offeringCore offering
The Sailing Academy delivers hands-on American Sailing Association (ASA) certified sailing courses from beginner to advanced offshore levels aboard a premium VIKO yacht fleet on Chesapeake Bay and seasonally in the Bahamas. Its commercial portfolio spans certified instruction (ASA 101-114 and Sailing Basics), bareboat yacht charters, a recurring Sailboat Club membership, multi-day family sailing vacations in the Bahamas and Chesapeake Bay, youth sailing camps (ages 5-15), and offshore passage experiences (Bay-to-Bahamas, Bay-to-Bermuda, DELMARVA Circumnavigation).
Product overview
The Sailing Academy operates as a sailing instruction and water sports education company offering a comprehensive portfolio of courses and services. The core offering consists of American Sailing Association (ASA) certification courses ranging from beginner (Sailing Basics, ASA 101) through advanced levels (ASA 103, 104, 105, 106, 114). These are delivered primarily from Chesapeake Bay (Tracys Landing, MD) and the Bahamas (Marsh Harbor/Abaco). Specialty programs include offshore sailing trips (Bay-to-Bahamas, Bay-to-Bermuda, DELMARVA Circumnavigation), youth sailing camps (Mini Mariners, Youth Sailing, CAPS), and family sailing vacations in both the Bahamas and Chesapeake Bay. The company supplements instruction with a Sailboat Club membership (premium yacht access), bareboat yacht charters (VIKO, Sabre, Jeanneau, Catalina, Beneteau vessels), and introductory programs (Try Sailing, Skill Builder sessions). The portfolio also includes destination-specific courses offered in tropical locations. The company is an ASA affiliate school since 2002, operating from Herrington Harbour Marina, and maintains a fleet of premium VIKO yachts.
Differentiator
Problem solved
Functional benefit
Brands
- Sailboat Club: Membership program offering guaranteed monthly sailing on chosen vessels with monthly sail credits to access shared yachts from May 1st through Nov 1st.
- Yacht Charters
Products and services
- Sailing Basics (2-Day Beginner Course)
- ASA 101 Basic Keelboat Sailing
- ASA 103 Coastal Cruising Course
- ASA 104 Bareboat Chartering
- ASA 105 Coastal Navigation
- ASA 106 Advanced Coastal Cruising
- ASA 114 Catamaran Cruising
- ASA 103/104 Combo Course (Chesapeake Bay)
- ASA 105/106 Combo Course
- Tracys Landing Combo Course (Sailing Basics + ASA 101)
- Bahamas ASA 103/104 Course
- Bahamas ASA 101 Course
- Bay-to-Bahamas Offshore Trip
- Bahamas-to-Bay Offshore Trip
- Bay-to-Bermuda Offshore Trip
- DELMARVA Circumnavigation
- Try Sailing
- Skill Builder Sessions
- Bareboat Yacht Charters
- Sailboat Club Membership
- Family Sailing Vacations - Bahamas (Abaco)
- Family Sailing Vacations - Chesapeake Bay
- Mini Mariners Youth Sailing Camp
- Youth Sailing Camp (Ages 8-13)
- CAPS (Coach Assistant Program)
Quantifiable outcome
- 30,000+ students trained over the years
- +2 more outcomes
Companies that use The Sailing Academy
Customer profileNamed customers6 records
Segments5 records
Ideal customer profiles5 records
The Sailing Academy technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Feature2 records
The Sailing Academy partnerships and signals
Strategic signalPartnerships
Three partnerships are on record, tiered core.
- Herrington Harbour MarinacoreMarina location where The Sailing Academy has operated since 2008 when they began offering courses to the general public (previously only club members). Primary location for sailing school operations and sailboat club.
- American Sailing Association (ASA)coreOfficial American Sailing Association affiliate school since 2002. Provides ASA certifications (101-118) including Basic Keelboat, Coastal Cruising, Bareboat Cruising, Coastal Navigation, Advanced Coastal Cruising, and Catamaran Cruising. Students receive ASA membership with certification.
- Planet Hope Land and SeacorePartnership with Planet Hope Land and Sea (a youth sailing and adventure organization) to provide sailing camps and courses for young people on the Beach at Herrington Harbour South. Programs include Mini Mariners (ages 5-7), Youth Sailing (ages 8-13), and CAPS leadership program (ages 13-15). Enrollment managed through sailingcamp.org.
Scale indicators7 records
Recent moves6 records
Expansion highlights6 records
The Sailing Academy competitors and assessment
Company assessmentDirect peers
- Blue Water Sailing School: ASA-affiliated sailing school offering basic through offshore certifications. Operates bluewater-focused offshore passages (including Bahamas-to-Annadel voyages) and liveaboard instruction directly comparable to the anchor's Bahamas and offshore passages programs.
- Offshore Sailing School: Founded by Steve and Doris Colgate, this is one of the most recognized ASA sailing schools in the US with multi-location curriculum (Florida, New York, British Virgin Islands). Comparable ASA curriculum, premium positioning, and tiered certification depth make it a strong comparable.
- Annapolis Sailing School: Established 1959 ASA-affiliated sailing school in Annapolis, MD on the Chesapeake Bay. Offers similar ASA certification courses (101-106), bareboat charters, and youth programs - directly competing for the same Chesapeake Bay customer base.
- J/World Annapolis Performance Sailing School: Performance-oriented ASA sailing school based in Annapolis, MD. Runs ASA certification courses and keelboat instruction in the Chesapeake Bay market, closely overlapping the anchor company's course offerings.
- Nautilus Sailing School: ASA-affiliated sailing school offering basic and bareboat certification courses. Comparable ASA curriculum and small private school positioning with similar product portfolio.
- Pineapple Sailing School: ASA-certified sailing school in the Chesapeake Bay area offering cruising courses and certifications. Direct geographic overlap with the anchor and a similar curriculum focus on adult certification and charter readiness.
Broad incumbents
- The Moorings: World's largest bareboat charter fleet operator with destinations globally (Caribbean, Mediterranean, Pacific). Significant incumbent competitor in the bareboat charter segment the anchor operates in, though without the ASA instructional focus.
- SailTime: Fractional sailing membership franchise offering shared yacht access through monthly dues. Direct comparable to the anchor's Sailboat Club membership model, with broader geographic footprint via franchise network.
- Dream Yacht Charter: Global bareboat charter company with extensive fleet and destinations worldwide. Comparable to The Moorings as a broad incumbent in the bareboat yacht rental segment directly competitive with the anchor's charter stream.
Regional players
- Herrington Harbour Sailing School / Sailing Center: Sailing program operated within Herrington Harbour Marina, the anchor's primary venue partner. Operates sailing lessons and youth programs in the same Chesapeake Bay geography with comparable instructional offerings.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat5 records
Key risks6 records
Key highlights7 records
Customer concentration
The Sailing Academy social profiles
Digital presenceThe Sailing Academy financial estimates
Financial estimateRevenue estimate
Valuation estimate
The Sailing Academy leadership team
Management profileNumber of profiles
Profiles6 records
The Sailing Academy funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
The Sailing Academy M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about The Sailing Academy
What does The Sailing Academy do?
The Sailing Academy delivers hands-on American Sailing Association (ASA) certified sailing courses from beginner to advanced offshore levels aboard a premium VIKO yacht fleet on Chesapeake Bay and seasonally in the Bahamas. Its commercial portfolio spans certified instruction (ASA 101-114 and Sailing Basics), bareboat yacht charters, a recurring Sailboat Club membership, multi-day family sailing vacations in the Bahamas and Chesapeake Bay, youth sailing camps (ages 5-15), and offshore passage experiences (Bay-to-Bahamas, Bay-to-Bermuda, DELMARVA Circumnavigation).
Is The Sailing Academy a public or private company?
The Sailing Academy is a private company. It is classified as family owned and is currently operating.
When was The Sailing Academy founded?
The Sailing Academy was founded in 2002. It employs 11 to 50 people.
Where is The Sailing Academy based?
The Sailing Academy is headquartered in Tracys Landing, United States, in the North America region.
How does The Sailing Academy make money?
Five revenue lines are on record. Sailing Courses and Certifications are the primary driver. The others are bareboat Yacht Charters, sailboat Club Membership, sailing Vacations and youth Sailing Camps.
Who are The Sailing Academy's main competitors?
Direct peers on record are Blue Water Sailing School, Offshore Sailing School, Annapolis Sailing School, J/World Annapolis Performance Sailing School, Nautilus Sailing School and Pineapple Sailing School. Broad incumbents are The Moorings, SailTime and Dream Yacht Charter. Herrington Harbour Sailing School / Sailing Center is listed as a regional player.
Does The Sailing Academy have an API?
No public API is recorded for The Sailing Academy.
What industry is The Sailing Academy in?
The Sailing Academy's product category is Maritime Sailing Instruction. Its primary akta.pro industry code is THAJAJAG, Sailing Experiences (Lessons, Regattas, Day Sails), with a secondary code of EDAOANAE, Navigation, Seamanship & Offshore Operations. Its NAICS code is 713930 and its SIC code is 8200.