Go to Annapolis Sailing Lessons - Schedule & Availability
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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 4-day Instant Cruiser® ASA 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.

Fair Wind Sailing School now offers sailing lessons in Annapolis. We have added a second Chesapeake Bay sailing school in America's sailing capital -- Annapolis, Maryland. Close to airports, easy access from Virginia, DC and Maryland and rich in sailing history, Annapolis is a perfect location for Chesapeake Bay sailing lessons. Fair Wind Sailing School offers our Instant Bareboater® sailing lessons. These sailing lessons feature the opportunity for weeklong, live-aboard sailing lessons and ASA certification at the ASA 101, 103, and 104 (Bareboat Chartering) levels. We will operate out of slip G-19 in Jabin's Boat Yard. For directions to Jabin's, click here.

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 Instant 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! See our Annapolis Sailing Lessons schedule here.

We also offer advanced sailing instruction in a complete circumnavigation of the Delmarva Peninsula. These are advanced sailing lessons covering the material in ASA 105 (Coastal Navigation) and 106 (Advanced Sailing). 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. Prerequisite for the advanced sailing lessons is prior certification in ASA 101. 103 and 104.

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.