Go to Annapolis Sailing Lessons - Schedule & Availability

New! Sailing Lessons in Annapolis

Fair Wind Sailing School operates from our Chesapeke Bay sailing school at Green Point Marina in Worton, Maryland where we offer a complete choice of ASA Sailing Lessons from Begninning through Ocean Passage, including our new Docking Bootcamp. Our 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 some of the most popular destinations on the bay and frequently visit St Michaels, Annapolis and the Baltimore Inner Harbor. The Upper Bay is an ideal location to learn how to sail or just cruise. 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. For a complete schedule from the Upper Bay, please visit our Chesapeake Bay Sailing School schedule.

New for 2008, Fair Wind Sailing School 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. For 2008, Fair Wind Sailing School will offer our Instant Bareboater sailing lessons. These sailing lessons feature the opportunity for weeklong, live-aboard sailing lesons 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 favoriteEastern Shore's pretties secluded anchorages. (click here to see a typical Instant Bareboater sailing lessons itinearary). 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.

Fair Wind Sailing School will continue to off our Instant Cruiser 4 day sailing lessons which provide ASA certifications at the 101 and 103 levels over an extended weekend in Worton, Maryland. These are the perfect classes for those preparing to day charter.

We also offer advanced sailing instruction in a complete circumnavigation of the Delmarva Penisnsula. These are advanced sailing lessons convering the material in ASA 105 (Coast Navigation) and 106 (Advanced Sailing). This fantastic sailing, covering a sail the entire length of the Chesapeake Bay and C&D canals, plus extended time in the open ocean and the Delaware Bay. While this sailing instruction is advanced, these sailing lessons are 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. Pre-requesite for the advanced sailing lessons is prior certification in ASA 101. 103 and 104. Our complete schedule can be found here: Chesapeake Bay Sailing School schedule.

We also offer Ocean Passage Sailing Lessons in our annual trip from the Cheasapeake Bay to Bermuda and then St Thomas, USVI.