SAILING . . . An exciting link to our romantic, seafaring past, ecologically in harmony with nature, and the perfect recreational pursuit for the new millennium. What's more, it is FUN and a skill that you can enjoy for a lifetime. Whether you are a novice searching for the perfect place to learn the basics or an experienced sailor seeking to fine tune skills, Chesapeake Sailing School offers the courses and qualified instructors that will charter the way. Since 1980, Chesapeake Sailing School has been developing and adapting its highly respected instructional programs to meet the needs of individuals and groups pursuing the joy and enthusiasm of the 'sailing life'.

We celebrated 30 years of sailing in 2010! Thirty years of Putting the Fun in Sailing.   We gathered old friends and new together 'on the hill', and are looking forward to to 2011 as we begin the next chapter...

Looking for the PERFECT GIFT? Gift Certificates are available for all of our programs!  And don't forget to Check us out on Facebook and Meetup for current news and upcoming events.

Voted "Best Sailing School for Adults" in Annapolis in 2012

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Be the FIRST TO KNOW about what is happening at CSS and on the water by joining us on Facebook! Or just send us your email and we will add you to the "SeaBag Messenger" for current & future sailing fun events.

Online bookings now available for Seminars, Tiller Club events and more on our Meetup page.