Tampa Bay · Cape Coral
Charlotte Harbor and Pine Island Sound bareboat operator working out of Tarpon Point Marina in Cape Coral. Sister to Florida Sailing & Cruising School. The same fleet runs ASA instruction one week and bareboat charter the next.
Southwest Florida Yachts is a bareboat operator based at Tarpon Point Marina in Cape Coral, dispatching a small fleet of cruising monohulls, a Jeanneau Sun Odyssey 440 and a Beneteau 38.1 as of September 2026, onto Charlotte Harbor and Pine Island Sound, one of the most forgiving cruising grounds in the state, with wide, protected water and short hops between Sanibel, Boca Grande, Cabbage Key, and Useppa.
The company shares its fleet with its sister business, Florida Sailing & Cruising School: the same boats run ASA instruction one week and bareboat charter the next. That gives a would-be charterer a clean path (earn the certifications on the boat, then take it out), and it means the fleet is maintained to a teaching standard. Bareboat trips require a cruising résumé on file and a demonstrated checkout rather than a certificate, with a captain available as an option for crews still building experience. The company says demand has outrun its fleet since Hurricane Ian, so book early.
Overnight and week-long liveaboard charters are the core offering, and the sheltered harbor makes it a common choice for first-time bareboaters stepping up from coastal daysailing.
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