Chesapeake Bay Sailing School

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New! Sailing Lessons in Annapolis

We have two sailing schools on the Chesapeake Bay. We operate the Upper Bay Sailing School at Green Point Marina in Worton, Maryland where we offer our 3-day Instant Cruiser® Sailing Lessons. These sailing lessons are great way for beginners to learn to sail or to prepare for day chartering. Our Upper Chesapeake Bay Sailing School provides some of the best sailing opportunities on the bay, with open water just 5 minutes from the dock. We are also close to the most popular destinations on the bay and frequently visit St Michaels, Annapolis and the Baltimore Inner Harbor. In addition, it provides convenient and easy access from all points on the Western Shore as well as Pennsylvania, New Jersey, Delaware and points north.

We also offer our Instant Bareboater® class.  This trip offers some of the finest sailing the Chesapeake Bay with typical visits to St Michael's, the Baltimore Inner Harbor and of course some of our favorite Eastern Shore secluded anchorages. (click here to see a typical Bareboater® sailing lessons itinerary). The Instant Bareboater® sailing instruction fee is inclusive of on board meals, mooring and docking fees and all other on board expenses (except alcohol). This is a great way to see the best of the Chesapeake Bay while learning how to sail! 

We also offer advanced sailing instruction in a complete circumnavigation of the Delmarva Peninsula. These are advanced sailing lessons covering the material in US Sailing's Coast Navigation course and the fun Night Time Sailing Course too.  This is fantastic sailing covering the entire length of the Chesapeake Bay and C&D canal, plus extended time in the open ocean and the Delaware Bay. While this sailing instruction is advanced, these sailing lessons are great fun (and ok, some hard work too!) covering just about all the sailing environments the East Coast has to offer. A super advanced sailing trip for the advanced sailor. 

We also offer Ocean Passage Sailing Lessons in our annual trip from the Chesapeake Bay to the Bahamas.

For more information, please visit our Chesapeake Bay sailing school FAQ page.  

Click here for our Chesapeake Bay Class Schedule.


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