Adventure brief
ASA 101 - Basic Keelboat
Master the essentials of keelboat sailing on Chesapeake Bay with SailTime Annapolis’s immersive two-day course. Learn, practice, and earn certification in iconic sailing waters.
SailTime Annapolis delivers a hands-on gateway into the world of sailing with its ASA 101 - Basic Keelboat course, set against the backdrop of Maryland’s vibrant capital city, Annapolis. Known as the “Sailing Capital of the United States,” Annapolis sits at the confluence of the Chesapeake Bay and the Severn River, offering a dynamic mix of tidal waters, scenic shorelines, and historic maritime culture that enrich every nautical experience. This intensive two-day course invites aspiring sailors aboard the Beneteau/ASA First 22, a reliable and responsive keelboat.
Through light to moderate winds typical of Chesapeake Bay spring and summer days, students dive straight into essential skills: sail trim, helm commands, navigation rules, and safety awareness. The curriculum balances technical instruction with on-water practice, ensuring each participant masters handling and seamanship under real-world conditions. SailTime Annapolis stands out for its small class sizes and seasoned instructor-captains who bring decades of local sailing expertise.
Beyond the classroom, completing the course earns sailors an ASA certification and a year-long American Sailing Association membership, opening up opportunities to rent a boat or charter with confidence. The area itself boasts unique features like the calm tidal flats of the Severn River and the historic Annapolis Harbor, dotted with classic schooners and racing yachts. These waters invite both beginners and experienced sailors to engage closely with Chesapeake Bay’s natural rhythms.
The city’s deep-rooted maritime history and commitment to environmental stewardship add a meaningful context to every voyage. SailTime Annapolis’s programs encourage sustainable practices, helping sailors appreciate and protect this iconic sailing hub. Whether new to boating or seeking formal certification, this course offers an accessible, authentic introduction to keelboat sailing in one of America’s most cherished sailing destinations.
Adventure tips
Plan your experience.
Curated tips for an optimal adventure.
- 01Dress in layersessential
Chesapeake Bay weather can shift quickly; layering helps you adapt to cool mornings and warmer afternoons on the water.
- 02Bring non-slip shoesessential
Deck surfaces get slippery when wet; shoes with good grip ensure safety while handling sails and lines.
- 03Stay hydratedinfo
Even on breezy days, you can lose fluids quickly—carry water to stay alert and comfortable during lessons.
- 04Listen for safety briefingsessential
Pay attention during pre-sail instructions to understand emergency procedures and safe boat handling practices.
Recommended gear
What to bring.
Waterproof jacket
Protects against wind and spray during variable weather on the bay.
spring|summer|fallEssentialSunglasses with UV protection
Reduces glare off the water and protects eyes during long afternoon sails.
summerEssentialNon-slip footwear
Improves footing on wet decks for safety and mobility.
EssentialReusable water bottle
Keeps you hydrated during active learning on deck.
EssentialLocal insights
Context for the journey.
Nearby secrets
Quiet coves on the Severn River for casual sails after class, Historic Thomas Point Shoal Lighthouse visible from course waters
Local fauna
Ospreys diving for fish, Blue crabs along the shoreline
Historic heritage
Annapolis has hosted elite sailing events since colonial times and remains a cornerstone of American sailing tradition.
Mindful exploration
Local organizations actively preserve Chesapeake Bay’s health, emphasizing clean water and habitat restoration for sustainable sailing.
Photography tips
Capture the moments
- Viewpoints
- From the boat looking back at Annapolis Harbor, Eastern Ave waterfront docks, Near the Thomas Point Shoal Lighthouse
- Subjects
- Sailboats under full sail, Reflections on Chesapeake Bay, Historic waterfront architecture
- Best times
- Golden hour, Midday with clear skies, Early morning mist
Frequently asked questions
Before you go.
Do I need any prior sailing experience to take this course?
No prior experience is required. The course is designed to introduce beginners to keelboat sailing fundamentals.
What certification will I receive upon completing this course?
Students earn the ASA 101 Basic Keelboat certification and a one-year American Sailing Association membership.
What is the typical class size for ASA 101 with SailTime Annapolis?
Classes keep small group sizes to ensure personalized instruction and hands-on practice.
Is the course weather dependent?
Yes. Lessons run in light to moderate wind and safe water conditions; rescheduling may be necessary for severe weather.
Can I rent a sailboat after completing the course?
Yes. Certification makes you eligible to rent ASA First 22 boats from SailTime and other members.
What should I wear for the two-day sailing course?
Wear layers, non-slip shoes, and bring sun protection to stay comfortable and safe on the water.