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Join a four-day sailing course in Middle River, Maryland, designed for beginners looking to master keelboat handling, earn certifications, and explore the stunning Chesapeake Bay coastline.
Join a four-day sailing course in Middle River, Maryland, designed for beginners looking to master keelboat handling, earn certifications, and explore the stunning Chesapeake Bay coastline.
Book with Starboard Sailing
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Operated by Starboard Sailing · Middle River, Maryland
Experience the thrill of sailing with Starboard Sailing’s four-day Basic Sailing and Coastal Cruising course in Middle River, Maryland. Designed specifically for beginners, this immersive adventure equips you with the knowledge and confidence to skipper a 25'-35' keelboat along Maryland’s scenic coastline. Throughout the course, you’ll learn essential sailing skills including navigation, docking, sail trim, and weather reading, all while enjoying breathtaking Chesapeake Bay views. Beyond hands-on instruction, the program awards you with ASA 101 and 103 certifications upon completion, plus a trial membership to keep exploring the waters long after the course ends. Whether you're aiming to sail for leisure or gear up for more advanced lessons, this experience sets the perfect foundation. With expert guidance and a friendly community on board, you’ll gain confidence, competence, and a love for coastal cruising while connecting with nature and the sea’s tranquility. Middle River’s calm waters and unique charm make it an ideal launchpad for your sailing journey.
easy.
4 days, roughly 6–8 hours per day.
Moderate fitness recommended to handle boat movements and physical tasks aboard
No prior experience is required. This course is designed specifically for beginners.
You will receive ASA 101 (Basic Keelboat) and ASA 103 (Coastal Cruising) certifications.
Bring non-slip shoes, sun protection, weather-appropriate clothing, and a water bottle.
Participants should be at least 14 years old and in good physical health.
Yes, hands-on practice skippering the keelboat is a core part of the program.
Sessions may be rescheduled or modified for safety if unsafe weather conditions arise.
Middle River has a rich maritime heritage linked to Chesapeake Bay’s shipbuilding and fishing industries.
The area is actively involved in preserving local water quality and blue crab habitats through community initiatives and clean boating practices.
Starboard Sailing operates from Annapolis, Maryland, offering a full range of ASA-certified sailing courses and instructor clinics. Using 25'–45' vessels, the program includes multi-day liveaboard courses and one-day clinics designed for both new sailors and experienced skippers seeking formal certification. Courses include Coastal Cruising (ASA 103/104/IPC), Advanced Coastal Cruising and Navigation (ASA 105/106), Cruising Catamaran training (ASA 114), docking and boat handling (ASA 118), and a series of Instructor Qualification Clinics (ASA 203, ASA 204, ASA 214 and full Instructor Qualification Clinic). Liveaboard courses focus on practical seamanship: sail trim, emergency procedures, navigation (traditional and electronic), anchoring, and skipper decision-making in coastal conditions. Instructor clinics equip candidates to teach on 30'–45' cruisers and 25'–35' keelboats, and include certified training materials and evaluation for qualification. The docking course is a concentrated day clinic with hands-on practice and an ASA 118 certificate. Starboard Sailing emphasizes safety, standardized ASA curriculum, experienced instructor evaluators, and clear certification outcomes that prepare students for chartering and advanced cruising. Starboard Sailing builds credibility through ASA-aligned syllabi, structured IQCs, liveaboard experience, and practical skills training—making it a reliable choice for sailors who want measurable progress, certified credentials, and real-world coastal cruising experience.
Book with Starboard Sailing