Set sail on a four-day liveaboard adventure in Middle River, Maryland, mastering coastal cruising and bareboat chartering with expert instruction and stunning Chesapeake Bay views.
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Difficulty
moderate
Duration
4 days
Fitness Level
Participants should have a moderate fitness level and be comfortable moving around on a boat, handling lines, and performing physically active maneuvers.
Wildlife
History
Middle River has a rich shipbuilding heritage and its waterways have long supported commercial and recreational boating.
Conservation
Efforts are ongoing to protect Chesapeake Bay's water quality and marine habitats, encouraging sustainable boating practices among sailors.
Starboard Sailing
Set sail on a four-day liveaboard adventure in Middle River, Maryland, mastering coastal cruising and bareboat chartering with expert instruction and stunning Chesapeake Bay views.
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.
Check Weather Forecasts Daily
Weather on Chesapeake Bay can change quickly, so review forecasts each morning before departure.
Wear Non-Slip Footwear
Boat decks can be slippery; use shoes with good grip for safety during maneuvers.
Stay Hydrated and Protect from Sun
Bring water and sun protection to avoid dehydration and sunburn on the open water.
Familiarize Yourself with Sailing Terms
Review basic sailing vocabulary before the trip to enhance learning and communication on board.
Non-slip sailing shoes
Ensures safety and stability while moving around the wet deck.
UV-protective clothing
Protects skin from strong sun exposure during long hours on deck.
summer
Waterproof jacket
Keeps you dry during rain showers and protects against wind.
spring
Hydration pack or water bottle
Important to stay hydrated under the sun and during active sailing.