• “Annapolis Sailing School lived up to its 50 year tradition of offering sailing courses that provide an excellent foundation for safe and effective sailing...”

    W.B. , Bethesda, MD
  • “Annapolis Sailing School has changed the way I sail. I've been sailing for 10 years and I learned more in these two days than the last 10 years.”

    H.G. , Owings Mills, MD
  • “When on the water I found it very effective when the instructor walked through the maneuver beforehand for context, explaining what would happen with the wind, boat, sails...”

    C.H. , Palo Heights, IL
  • “[The Instructor] was great, he taught us to not only react but anticipate what move we should be ready to do. This course has made me more excited to learn more...”

    J.G. , Minneapolis, MN

certification Modular Courses

Basic Keelboat courses can be taken as one day modules in order to accommodate any schedule and let students focus on topics of their choice


Basic Courses

Our Basic Courses are designed to provide an enjoyable introduction to the sport of sailing.Our courses will give you the necessary basic knowledge to enjoy sailing.  

Cruising Courses

When you’re ready to step up to handling a larger cruising sailboat, we can help. We also have refresher courses for those who have some “big boat” experience but want to hone their skills. 

Popular at The Sailing School

  • Learn To Sail

    Come take a class. Experts and amateurs welcome!
    11755104 1006745692690875 1148811817935041135 n

    Learn Sailing on Your Schedule

    Take any of our modules that range from the basics to refinement of skills.
    beginning classes

    Save on Modules

    Save on our basic sailor modules when you purchase a them together as a course.
    IMG 7617

    Evening Sails

    Book an evening sail and enjoy a beautiful sunset cruise on the Chesapeake Bay.

S5 Box



You need to enable user registration from User Manager/Options in the backend of Joomla before this module will activate.