Tampa Bay · Gulfport
Private liveaboard ASA instruction for couples and families from Gulfport Municipal Marina, on a pair of air-conditioned Hunter 295s. Two to seven days aboard on Boca Ciega Bay; the instructor goes home each evening and you keep the boat.
The format is the whole pitch: private instruction only, for couples and families, taught liveaboard on Hunter 295s fitted with air conditioning, hot water, and chartplotters. The instructor teaches through the day and leaves each evening, so students get the boat, and the practice of actually living on it, to themselves. Kids can join free within limits, and linens and cookware come with the boat.
Courses stack from Basic Keelboat (101) in two days to a seven-day run through Bareboat Cruising, Coastal Navigation, and Advanced Coastal Cruising (104, 105, 106), and most end with a day of solo chartering practice. The advanced courses are taught on real repositioning passages: the Gulf, the ICW, the Keys, rather than laps of the bay.
SmarterSail has taught out of Gulfport since around 2008, moving to the municipal marina in 2022, with Boca Ciega Bay off the dock and the open Gulf about forty-five minutes out. Instructor Gary Wall took ASA’s Outstanding Instructor award in 2014, and the staff are USCG-licensed captains.
Featured Tampa Bay · Sarasota
Founded by Olympian Steve Colgate in 1964 and relaunched in 2026 under Seaworthy Academy, teaching from the Quay in Sarasota and the Vinoy Marina in St. Petersburg. NauticEd pathway from Learn to Sail to Bareboat Charter Master, on 40 to 48 foot monohulls and catamarans.
Tampa Bay · Fort Myers Beach
Small instructor-led NauticEd school sailing from Matanzas Pass at Fort Myers Beach on a Beneteau 323. Certify locally through Bareboat Charter Master and the SLC license, then apply it on the school's week-long international flotillas.
Tampa Bay · Punta Gorda
US Sailing-certified school out of Burnt Store Marina on Charlotte Harbor, running coastal cruising, liveaboard, and offshore courses on a fleet that includes Beneteau Oceanis monohulls and Excess catamarans.