The Keys · Marathon
Middle-Keys ASA school running the full coastal-cruising pathway from Basic Keelboat through Advanced Coastal Cruising out of Marathon.
Everything here is private (the school’s own emphasis, capitals theirs): classes, day sails, and charters run for your party alone, never assembled groups. Teaching in the Keys has run this way at Florida Keys Sailing since the 1990s, which makes it one of the older sailing schools working anywhere in the islands.
The base is Keys Fisheries Marina on the gulfside of Marathon at mile marker 49, working-waterfront Keys rather than resort Keys, with the flat, protected waters of Florida Bay off the dock and Hawk Channel a bridge away when a course needs open water. The fleet is honest cruising stock: a Catalina 30, an Irwin 34, a Catalina 36. These are the boats students will actually charter later.
Formats run from a two-day beginner fundamentals course to seven-day live-aboard bareboat programs, with the live-aboard sailing vacation (course and cruise at once) as the signature offering. For a couple that wants the bareboat ticket and a week in the Middle Keys in the same booking, this is exactly the shape of school to want. The 101 is discounted for veterans, active military, and reservists through ASA’s Veterans Sailing Education Program.
The Keys · Key Largo
ASA school on Buttonwood Sound, teaching from the Key Lime Sailing Club cottages at mile marker 99. Courses run on demand 363 days a year; stay in a cottage, learn on Florida Bay, and keep sailing the club's Catalina 22s free after you certify.
The Keys · Key West
Catamaran charter operation at Stock Island Marina Village with an ASA school built in, teaching Basic Keelboat through catamaran cruising on multi-day training cruises. Courses run as customized liveaboards toward the Dry Tortugas, the Marquesas, or the Bahamas.
The Keys · Key West
Key West ASA school sailing from Stock Island since 2014, in classes of two to four on the calm Gulf side of the island. Veterans train at no charge one weekend a month through the winter season.