Since 1998, Flagship Sailing has helped sailors of every level build real, lasting skill on Tampa Bay, one of Florida’s most accessible and rewarding cruising grounds. This area boasts steady breezes, open water, and easy access to the Gulf of America. We’re based at Little Harbor Marina in Ruskin, FL, a close reach to some of the state’s most beautiful coastline.
Our ASA-certified curriculum takes sailors from Basic Keelboat (ASA 101) to Offshore Passagemaking (ASA 108), taught by instructors who are both ASA-certified and USCG-licensed, including women instructors and a Master Instructor on staff.
What sets us apart is where our training can take you. Beyond our on-the-water courses, we run multi-day training cruises several times a year: a coastal cruising adventure along Florida’s west coast that builds real ASA 104-level skills in chart work, depth awareness, daymarks, and drawbridge navigation through the Intracoastal Waterway, and an offshore passage to Key West for sailors ready to test those skills on open water. Both are genuinely hands-on. You’ll be crewing the boat, not watching from the dock.
Our fleet includes a 22-foot Catalina sloop for beginners, a 31-foot Catalina for building skills, and a 41-foot Hunter for multi-day offshore trips.
We’re proud to offer a discount to veterans and first responders. We welcome sailors of every background, from someone who’s never touched a line to a boat owner sharpening specific skills. If you’re ready to build real confidence on the water, we’d love to have you aboard.
