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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
moderate
Duration
3.5 days
Fitness Level
Participants should be comfortable with physical activity and able to manage some movement on deck.
Wildlife
History
Maryland’s Chesapeake Bay has been a hub of maritime activity since the 17th century, shaping local communities and navigation traditions.
Conservation
Starboard Sailing emphasizes eco-friendly practices, including responsible anchoring and minimal ecological impact to preserve Chesapeake Bay's fragile ecosystem.
Starboard Sailing
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.
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.
Prepare for variable weather
Check the forecast and pack layers to stay comfortable on the water.
Bring sun protection
Use sunscreen, hats, and sunglasses to shield against the sun during daytime sailing.
Practice emergency drills
Participate actively in safety exercises to ensure confidence in unexpected situations.
Get familiar with navigation tools
Review basic chart reading and GPS use before your trip start.
Sunscreen
Protect your skin from sun exposure during long hours on the water.
summer
Hat and sunglasses
Shield your eyes and face from the sun for better visibility and comfort.
summer
Layered clothing
Dress in layers to handle changing weather conditions on the water.
spring;summer;fall
Personal flotation device
Always wear a PFD for safety during sailing trips.