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 are offered a discover-sailing cruise and a discount on the courses, one weekend a month through the winter season.
Captain Brad Lockwood founded the school in 2014 and still runs every class: thirty-plus years on the water, more than a thousand sailors trained, “70 years young” by his own count, and a veteran himself. Classes are two to four students, nine to four, hands-on from the first hour.
The teaching water is a deliberate choice. The school sails the Gulf side of Key West, where the island blocks the Atlantic swell, so beginners learn in flat water instead of fighting four-foot chop; Basic Keelboat (101) runs in two days, with Basic Coastal Cruising (103), Bareboat Cruising (104), and the docking endorsement (118) behind it.
The veterans program is the standout: the second weekend of every month from November through May, up to four veterans are taken out on a discover-sailing cruise and offered a discount on the school’s courses. For everyone else the school is the certification answer at the bottom of the island chain, based at Sunset Marina on Stock Island, a mile and a half from the airport.
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.