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Set sail on a 3.5-day liveaboard adventure with Starboard Sailing in Maryland. Master navigation, sail trim, and emergency protocols aboard a classic sloop. Perfect for aspiring sailors seeking certification and scenic waters.
Set sail on a 3.5-day liveaboard adventure with Starboard Sailing in Maryland. Master navigation, sail trim, and emergency protocols aboard a classic sloop. Perfect for aspiring sailors seeking certification and scenic waters.
Book with Starboard Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by Starboard Sailing · Middle River, Maryland
Maryland's coastline offers a perfect backdrop for sailors eager to take their skills to new heights. Starboard Sailing specializes in providing hands-on sailing experiences that combine skill development with the thrill of open water. Their flagship offering, the 3.5-day liveaboard adventure, is an immersive journey tailored for those ready to helm their own vessel. Participants learn essential techniques, including coastal navigation, emergency procedures, and sail trim, all while cruising aboard a 30'-45' sloop-rigged sailboat. The goal? To earn ASA 104 certification and gain the confidence to command your own boat.
Based out of Maryland, a state rich in maritime history and scenic anchorages, Starboard Sailing’s trips bring sailors to some of the area’s most picturesque spots. You'll stop at pristine coves and hidden inlets, often inaccessible by land, where quality time at anchor offers spectacular sunsets and tranquil waters. The region’s unique blend of Chesapeake Bay ecology, with its vibrant birdlife and dynamic tidal systems, creates a captivating environment for both beginners and seasoned sailors.
What makes Starboard Sailing a standout? Their focus on personalized instruction combined with the vibrant local waters makes each trip an intense, rewarding experience. Whether you're aiming to earn your ASA 104 certification or simply sharpen your skills, this adventure offers practical, real-world sailing in a scenic, accessible setting. Maryland’s maritime legacy and the warm, experienced crew at Starboard Sailing make each voyage memorable — a true highlight for any aspiring sailor.
For anyone looking for a comprehensive, adventure-packed introduction to sailing, this trip offers both the challenge and the beauty of Chesapeake Bay, mixed with expert guidance and community camaraderie. It’s more than just a sailing trip; it’s a compelling leap into the world of coastal navigation and boat handling at sea.
moderate.
3.5 days.
Participants should be comfortable with physical activity and able to manage some movement on deck.
No prior experience is necessary; this trip is designed for beginners and those looking to improve their skills.
You'll earn ASA 104 certification in coastal navigation and sail trim, validated upon successful completion.
Yes, meals and beverages are included during the trip.
Sea sickness can be managed with over-the-counter remedies; alert your crew if you feel unwell.
Bring comfortable clothing, sun protection, personal items, and any necessary medications.
Guests are welcome for certain activities but must adhere to safety protocols.
Maryland’s Chesapeake Bay has been a hub of maritime activity since the 17th century, shaping local communities and navigation traditions.
Starboard Sailing emphasizes eco-friendly practices, including responsible anchoring and minimal ecological impact to preserve Chesapeake Bay's fragile ecosystem.
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