ASA-certified catamaran and keelboat courses, instructor clinics, and navigation training taught as liveaboard and day clinics from Annapolis, Maryland.
From one-day instructor qualifications to multi-day liveaboard certifications — practical, skill-focused sailing experiences.
boat-charters · Middle River
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Chesapeake Bay departure point
Instructor and student courses available
Short clinics and multi-day liveaboards
Beginner to advanced class range
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Starboard Sailing listing.
Starboard Sailing offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Check available dates for ASA courses and instructor clinics—book a liveaboard or day clinic and advance sailing skills from Annapolis.
others · Middle River
Become a certified ASA 204 Bareboat Chartering Instructor in just one day with expert training from Starboard Sailing in Middle River, Maryland. Discover how this immersive course can advance your sailing skills and teaching credentials.
others · Middle River
Become a certified coastal cruising sailing instructor in just one day in Middle River, Maryland. Learn essential instructor skills with hands-on training on beautiful Chesapeake Bay waters.
others · Middle River
Earn your ASA Sailing Instructor certification in just three days with Starboard Sailing near Middle River, MD. Gain essential skills and internationally recognized credentials while training on the beautiful Chesapeake Bay.
others · Middle River
Learn to skipper a keelboat with a private three-day Coastal Cruising ASA 103 course in Middle River, Maryland. Build hands-on experience sailing Chesapeake Bay and boost your confidence on the water.
others · Middle River
Master the essential skill of docking boats safely with Starboard Sailing’s ASA 118 course in Middle River, Maryland. Gain hands-on experience and earn certification in one immersive day!
boat-charters · Middle River
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.
boat-charters · Middle River
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.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.