Windward Sailing is a Fernandina Beach, Florida sailing provider offering guided day sails, sunset cruises, and structured sailing courses along the northern tip of Amelia Island. The company operates both monohull and catamaran options for recreational sails and instruction.
Trips include the Sea-breeze (8AM to Sunset) experience, where guests can sail along Amelia Island’s northern tip and look for dolphins and wild horses. Instructional offerings range from Intro To Sailing to certified-style courses, including Basic Keelboat Class 101 — an 18-hour program for learning to handle 25–30 foot boats in light to moderate conditions.
Hands-on clinics use a Hunter 34 to give practical on-water practice and preparation for ASA qualifications. Multi-day combos provide extended time aboard and progressive skill development: Combo Course 103/104 is a four-day progression focused on local and coastal cruising; Combo Course 101/103/104 is a 6.5-day package with two nights on the water and five meals included; Combo Course 101/103 offers a 4.5-day training pathway.
Windward Sailing operates from Fernandina Beach and emphasizes safety, seamanship, navigation, and practical boat handling. Instructors deliver hands-on teaching aboard appropriately sized keelboats and the Hunter 34 for clinics. Trips and courses are bookable through The Adventure Collective listing or by contacting Windward Sailing directly. Boats include both monohull and catamaran options, and sessions accommodate individual guests and small groups for private or shared experiences.