About Windward Sailing
Windward Sailing brings true sailing to Amelia Island, operating private charters and an American Sailing Association school out of Fernandina Harbor Marina. Every charter is private — just your group and a USCG-licensed captain — sailing the Amelia River, Cumberland Sound, and out toward the Atlantic, with dolphins, wild horses on the Cumberland shoreline, and pelican squadrons as the regular supporting cast.
Charters run day and evening, and because the boats are not tide-limited, guests choose the departure time that suits them, with sunset sails the perennial favorite. On the instruction side, Windward is a full ASA sailing school teaching the 101, 103, and 104 certification sequence, taking students from first tack to bareboat-competent cruiser. Graduates and experienced sailors can also arrange bareboat charter packages on the company's Hunter 34 monohull or Voyage 37 catamaran.
The blend of private charters, serious instruction, and bareboat access makes Windward the most complete sailing operation on this stretch of coast. Reviews consistently praise the captains' depth of knowledge and easygoing teaching style — several students complete the full certification ladder here in a single trip. The office is on South 8th Street, with all sailing departing from the downtown marina at Front Street.
