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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.
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.
Book with Starboard Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by Starboard Sailing · Middle River, Maryland
Experience an invigorating four-day liveaboard sailing adventure with Starboard Sailing in Middle River, Maryland. Designed for those aiming to master essential sailing skills, this trip guides you through operating 30'-45' sloop-rigged boats while navigating the picturesque Chesapeake Bay waters. Alongside honing critical techniques like advanced sail trim, emergency procedures, and navigation, you’ll earn your ASA 103/104 and IPC certifications, validating your readiness for independent coastal cruising. The course balances hands-on instruction with ample time to explore Maryland’s stunning coastal environment. Whether you’re steering past serene inlets or mooring at charming local harbors, every moment showcases the region’s rich maritime heritage and natural beauty. Ideal for adventurous sailors looking to gain confidence and credentials, this immersive journey by Starboard Sailing offers a solid foundation for future bareboat charter vacations anywhere in the world.
moderate.
4 days.
Participants should have a moderate fitness level and be comfortable moving around on a boat, handling lines, and performing physically active maneuvers.
While some basic sailing experience is helpful, this course is designed to build on foundational skills and prepare you for ASA certifications.
You'll sail on 30'-45' sloop-rigged monohull boats that are ideal for coastal cruising and beginner to intermediate sailors.
Meals are typically self-catered; participants should plan to bring their own food or arrange provisions before departure.
Yes, upon successful completion you will receive ASA 103 Coastal Cruising, ASA 104 Bareboat Chartering, and IPC certifications.
The course requires moderate physical effort including handling lines and moving on deck, so being in moderate shape is recommended.
Yes, although spring through fall is most popular, winter courses are available with extra preparation for cold weather.
Middle River has a rich shipbuilding heritage and its waterways have long supported commercial and recreational boating.
Efforts are ongoing to protect Chesapeake Bay's water quality and marine habitats, encouraging sustainable boating practices among sailors.
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