Coconut Grove Sailing School

Captain Jeff runs the school personally out of Dinner Key in Coconut Grove: booking a class means calling him directly, and the private and small-family format follows from that. No experience is required to start, and Biscayne Bay does the rest: it is the most forgiving serious training water in Florida, big enough for real passages and protected enough that a first-time family is never in over its head.

Basic courses teach on a sloop-rigged keelboat in the 20-to-27-foot range; the advanced end moves onto catamarans. The pathway runs from Basic Keelboat through Coastal Cruising, Bareboat Captain, and Coastal Navigation to the Cruising Catamaran ticket. The school’s intensive packs the whole run, 101 through 114, into a single week for students who can commit the time.

The live-aboard option is the distinctive offer: spend the week living on the boat at Dinner Key while earning the certification, which turns a course into something closer to a shakedown cruise for the life the certification is for. Veterans, active military, and reservists get a discounted 101 through ASA’s Veterans Sailing Education Program.