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.
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Difficulty
easy
Duration
4 days, roughly 6–8 hours per day
Fitness Level
Moderate fitness recommended to handle boat movements and physical tasks aboard
Wildlife
History
Middle River has a rich maritime heritage linked to Chesapeake Bay’s shipbuilding and fishing industries.
Conservation
The area is actively involved in preserving local water quality and blue crab habitats through community initiatives and clean boating practices.
Starboard Sailing
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.
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.
Base Location
Annapolis, MD
Chesapeake Bay departure point
Certifications
ASA Certifications
Instructor and student courses available
Course Lengths
1–4.5 days
Short clinics and multi-day liveaboards
Tours Offered
10 courses
Beginner to advanced class range
Check available dates for ASA courses and instructor clinics—book a liveaboard or day clinic and advance sailing skills from Annapolis.
Wear Non-Slip Boat Shoes
Opt for shoes with good traction to stay safe on wet decks while maneuvering the boat.
Stay Hydrated and Use Sunscreen
Exposure to sun and wind on the water can be intense—protect your skin and keep water nearby.
Listen Carefully During Docking Practice
Mastering docking is tricky but essential; focused attention here can make all the difference.
Check Weather Before Trips
Weather conditions on Chesapeake Bay can change rapidly; always review forecasts and be prepared.
Non-slip sailing shoes
Provide stability and safety on wet boat surfaces.
Waterproof windbreaker
Keeps you warm and dry against coastal winds and light rain.
spring
Polarized sunglasses
Reduce glare on the water for better visibility and eye protection.
summer
Wide-brimmed hat
Offers additional sun protection during sunny sailing days.
summer|spring