Sara-Bay Sailing School & Charters

The teaching roster is four USCG-licensed captains. Bill Brooker holds a 100-ton Near Coastal Master ticket with more than fifty years of sailing behind it, and two of the others have each spent over a decade as ASA instructors. The fifth name on the team page, First Mate Barney, is a dog.

Sarasota Bay makes an orderly classroom: light easterlies through the morning, then a west sea breeze that fills in at 10 to 15 knots after lunch, so a course day starts in drill-friendly water and finishes in real wind. Basic Keelboat (101) seats two students, three at most, which buys each of them most of a day on the tiller.

The boats grow with the course. 101 teaches on a Catalina 22; Bareboat Cruising (104) moves to a 35-foot sloop for a two-day cruise that works the Gulf, the Intracoastal, and the bay in a single pass, with the student running the boat as skipper and crew. Cruising Catamaran (114) rides on top as a one-day addendum, and the Catalina 22 rents bareboat afterward to anyone who has passed Basic Coastal Cruising (103).

Captained charters run half or full days on the bay, on the Catalina 22 or the six-passenger Nightwind 35. Veterans get ten percent off instruction through ASA’s Veterans Sailing Education Program.