Windward Sailing

Windward Sailing School started in 1997 and has been an American Sailing Association affiliate school since 2000. We have won ASA Outstanding School 4 times and 3 of our instructors have received an ASA Outstanding Instructor award, certifying hundreds of sailors on the process. We currently have 9 certified ASA instructors.

Our sailing area offers deep water sailing inshore and offshore with easy access to the Atlantic. Our boats are docked on the Inter Coastal Waterway (ICW) and we are able to sail right off the dock and year-round.

Windward Sailing also offer private, captained charters, catering for romantic getaways, family fun, and social and corporate events. Whether you join us for a sail on one of our keelboats or stretch out on the trampoline of the catamaran, one of our friendly US Coast Guard licensed captains will share the magic of sailing as well as the sights and history of Amelia Island.

Explore the beautiful Cumberland Sound with its wildlife, Fort Clinch, and wild Cumberland Island horses. Extend your charter and we might venture into the Atlantic Ocean, or visit St Marys GA for lunch

  • Key Details
  • Discounts: Military
  • Hours of Operation:
  • MON: 9:00 AM - 5:00 PM
  • TUE: 9:00 AM - 5:00 PM
  • WED: 9:00 AM - 5:00 PM
  • THU: 9:00 AM - 5:00 PM
  • FRI: 9:00 AM - 5:00 PM
  • SAT: 9:00 AM - 5:00 PM
  • SUN: 9:00 AM - 5:00 PM



Award-winning American Sailing Association School

Weddings at Windward Sailing

Fun Sails Are Great For romantic getaways, family memories, social events, small weddings, and even corporate charters


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Meetings at Windward Sailing

We offer team building events and corporate regattas aboard sailboats, up to 7 boats at once. We sail from Fernandina Harbor Marina out to Cumberland Island, and beyond, into the ocean, or to St. Mary's, Georgia.

All of our charters are private. These are on sailboats with cabins below with restrooms.

Key Details:
  • Max Attendees: 22


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