• “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


Very early in the history of Annapolis Sailing School we realized that the best way to learn to sail was by sailing. All of our instruction, whether introductory or advanced, reflects this commitment to hands on, experience-based learning.

Some concepts are best conveyed in a classroom setting, and there is a place for formal theory in any learning program. The “Annapolis Way,” however, blends a minimum of theory with a maximum of hands on experience. In most of our introductory courses, students will be on the water, actually sailing, within an hour of the start of the class...

Beginner's Courses

Our beginner’s courses are designed to provide an enjoyable introduction to the sport of sailing.Our beginner’s level courses will give you the necessary basic knowledge to enjoy sailing.  

Certification Process

Of the many competing systems currently available we have identified the American Sailing Association system as the best and now offer it to our students as an extra cost option. 

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. 

Weather Forecast




Wind: N at 5 mph
48°F / 53°F
43°F / 56°F
36°F / 49°F

Current Conditions

Tampa Bay Location

  • Visiting St Petersburg, Florida?

    Come take a course in our Florida branch!

    Learn to Sail on a Hunter 36

    Course 122 is an introductory course designed for beginners with no prior sailing experience, but who do not want to learn on a small keelboat.

    Become a Sailor in One Weekend

    Course 132 is designed for people with previous sailing or boating experience. This course is taught entirely on board a cruising auxiliary and can be tailored exactly to the needs of the student.

    Weekend Intro to Cruising

    In two days and one night aboard, students can sample the joys and challenges of living and cruising on a sailboat. Many peaceful and attractive anchorages are attainable in a one-day sail from St. Pete
  • Visiting or Live In Tampa Bay?

    Take a course at our Florida branch!

    Tampa Bay Country Cruising Course

    Our Tampa Bay Country Cruising Course is designed for experienced small boat sailors who want to experience the cruising lifestyle. For one low tuition cost we provide it all: the boat, provisions, bedding and the round-the-clock services of an on board instructor.

    3 Day ASA Certification Course

    Designed for students who have already achieved the ASA 101 certification, this is the next step in ASA’s certification program. This is a live-aboard course that provides a hands-on introduction to cruising.

    Prep for Bareboat Chartering

    Most new sailors seem to have a plan, either immediate or long term, to bareboat charter in some exotic location such as the Caribbean, Europe or the South Seas.

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