The Keys · Tavernier
Upper Keys ASA school founded by a Navy SEAL, with a "crawl, walk, run" curriculum built around veterans, their supporters, and couples. Active-duty and honorably discharged military earn their ASA certifications free of charge.
The headline fact deserves to be stated plainly: 375 veterans have learned to sail here for free, by the association’s own count. The association is a 501(c)(3) nonprofit, and for active-duty military and honorably discharged veterans the course fees are simply waived. Not discounted, waived. Everyone else (couples, supporters, civilians) pays ordinary tuition.
The instruction itself holds up on its own terms; the founder took ASA’s Instructor of the Year award in 2023 and again in 2025. The curriculum runs Basic Keelboat (101) and Basic Coastal Cruising (103), with a couples-only course alongside. Courses run from Tavernier in the Upper Keys, and the curriculum leans on where it is: students sail, snorkel, spearfish, kayak, and run eco-tours through the reefs, mangroves, and backcountry waterways of the Keys as part of learning to handle a boat. That mix is deliberate: the “crawl, walk, run” structure builds competence in layers, and the Keys make every layer worth showing up for.
For a veteran anywhere in Florida thinking about sailing, this is the obvious first call. For anyone else, it is a small Keys school with an unusually decorated instructor, where the tuition does double duty.
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 · Marathon
Middle-Keys ASA school running the full coastal-cruising pathway from Basic Keelboat through Advanced Coastal Cruising out of Marathon.
The Keys · Key Largo
Nonprofit youth sailing program on Buttonwood Sound, sailing from the Upper Keys Sailing Club beach in Key Largo. Summer, fall, spring and homeschool sessions for ages 6 to 18 in Optis, Club 420s and RS dinghies, scholarships, and host of the Buccaneer Blast each February.