Windward Sailing School
Amelia Island, North East Florida
| (904) 441-9105 |

Windward Sailing has been in business since 1997 and has certified hundreds of sailors. Our sailing area offers deep water sailing in shore and offshore with easy access to the Atlantic. Our boats are docked on the 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 and sail year-round. A student can expect to find an array of conditions and circumstances that would be useful for future sailing.

Windward Sailing offers combo courses that are competitively priced, as well as normal ASA courses. We offer bareboat chartering, captained charters, and private lessons. We have won ASA Outstanding School 4 times and 3 of our instructors have received ASA Outstanding Instructor.

American Sailing Certifications Offered

ASA 101, Keelboat Sailing 1
ASA 101, Keelboat Sailing 1
Learn to skipper a 20' - 27' sloop-rigged keelboat by day, in light to moderate winds and sea conditions. Learn basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards.
ASA 103, Coastal Cruising
ASA 103, Coastal Cruising
Learn to skipper a sloop-rigged auxiliary powered 25'-35' keelboat by day in moderate winds and sea conditions. Learn cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather, safety and seamanship.
ASA 104, Bareboat Cruising
ASA 104, Bareboat Cruising
Learn how to sail a sloop-rigged, auxiliary powered 30'-45' sailboat during a multi-day cruise upon inland/coastal waters in moderate/heavy winds and sea conditions. Learn about provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring / mooring, docking, emergency operations, weather, and more.
ASA 106, Advanced Coastal Cruising
ASA 106, Advanced Coastal Cruising
Learn to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.
ASA 114, Cruising Catamaran
ASA 114, Cruising Catamaran
Learn to skipper an auxiliary-powered sailing cruising catamaran of approximately 30-45' feet in length during a multi-day liveaboard cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions.
ASA 118, Docking Endorsement
ASA 118, Docking Endorsement
The successful sailor will have the knowledge and skills to safely and competently dock and maneuver a sailboat under auxiliary power in a variety of conditions. Includes knowledge of steering and propulsion theory, wind and current, single and double-rudder monohulls, catamarans, safety precautions, knots and line handling, fixed and floating docks.

Other Services Available

  • Couples Courses
  • Private Courses
  • Weekday Courses
  • Weekend Courses
  • Corporate Team Building Courses
  • ASA 'Challenges'
  • Day Sail Charters (public)
  • Sunset Cruises


ASA Veterans Sailing Education Program - Sign Up Now >>

At ASA we recognize the sacrifices made by the brave men and women who have served or are serving in our country's armed forces. As a token of our appreciation, and our way of saying thank you, we are inviting veterans and active military personnel to share our passion for sailing by offering a discount on our ASA 101 Basic Keelboat Sailing course. Windward Sailing School is offering a minimum of $50.00 or 10% off their ASA 101 Basic Keelboat Sailing course.

Sailing School Reviews / Testimonials

  • Last week, my son, Zach and I took the ASA 101 class. We had Charlie Weaver teach the classroom portion and Jerry Miller handle the on the water instruction. I just want you to know how very pleased we were with all aspects of this

    Jeff Linder - ASA 101, Keelboat Sailing 1

  • I want to thank you for accommodating my schedule in the recent 105 class. Jerry is a great teacher who has the experience to give the content of the class real meaning. He was very patient and clearly interested that we learn the material

    Jonathan Brewster - ASA 105, Coastal Navigation

  • Charley's name appears in the current ASA Bearings newsletter as part of the National Standards Committee. His challenge to become a 'subject matter expert' continues to be resonant with every student I instruct.

    Marla Keith - Windward Sailing School

  • I thought you'd enjoy reading this review that recently came through for Dominic DiFrancesco. Thanks for always doing an awesome job and taking such great care of our customers, it's greatly appreciated.

    Dominic DiFrancesco - Windward Sailing School

  • We had a wonderful time, it was the highlight of our Amelia Island stay! Captain Tony was courteous, very knowledgeable and well seasoned. He was both informative of the area and demonstrated excellent sailing skills.

    Sam Enfinger - Windward Sailing School

Contact Information

Windward Sailing School

Address 714 Beech StreetAmelia IslandFL32034United States
Phone (904) 441-9105
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