On the water classes offered through mid-Nov

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'.

Need a refresher before your course or first rental?  Our 1st DVD "Basic Sailing" is now available.  Formatted after our highly successful Basic Course. Just call today to purchase for only $25 today!

We turned 30 in 2010! Thirty years of Putting the Fun in Sailing, and we can't wait to celebrate with our graduates and new students.  Keep an eye out for our 30th Anniversary Party dates in 2010 where we'll have prizes, giveaways and contests celebrating the history and 'sea stories' of Chesapeake Sailing School, the Tiller Club and our Charter Company.