Windward Sailing

Windward Sailing School started in 1997 by Captain Charlie and was purchased by Tony and Cindy Jones in 2006. For 17 years Tony and Cindy thoughtfully grew and nurtured the business; attracting loyal customers and experienced USCG qualified charter and sailing school captains. Roelie and Sharon Le Roux bought the business in 2022 to shepard the business on its next phase.

Windward Sailing has been an American Sailing Association affiliate school since 2000 and has won ASA Outstanding School 4 times and 3 of our instructors have received ASA Outstanding Instructor, 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. Currents here are strong and offer challenging conditions, as well as pristine sailing areas. We have favorable winds for year-round sailing. A student can expect to gain experience in an array of conditions and circumstances.

Windward Sailing offers combo courses that are competitively priced, as well as stand alone ASA courses. We also offer bareboat chartering, captained charters, and private lessons.