Regattas, race series, and championships hosted by clubs and schools across Naples.
Gulf Coast Sailing Club · Details at gulfcoastsailingclub.org ↗
The club's season-opening Boat of the Year distance race up the coast from Naples to Fort Myers Beach, open to everyone.
Gulf Coast Sailing Club · Details at gulfcoastsailingclub.org ↗
The first Boat of the Year regatta of 2027, short races of about 20 minutes each on triangle buoy courses.
Gulf Coast Sailing Club · Details at gulfcoastsailingclub.org ↗
Boat of the Year pursuit race, slowest boats first, with a beat about 12 miles down the coast to the Caxambas Pass mark and a downwind leg to the finish.
Live wind and sky, spot by spot, straight from the National Weather Service. Each card opens the full point forecast. NWS Tampa Bay marine forecast →
Member-driven yacht clubs and community sailing centers. See all Florida clubs →
Private Tampa Bay · Naples · est. 1974
Southwest Florida's racing and cruising club since 1974, drawing sailors from Marco Island to Punta Gorda: offshore, distance, pursuit, and buoy racing under PHRF, a casual summer series, plus day sailing and cruising.
View details →
Community Tampa Bay · Naples · est. 1991
Nonprofit community sailing center on Naples Bay, teaching Naples-area kids to sail since 1991: week-long summer camps from age seven, then Optimist race teams and a C420 high-school team that train through the school year and race the Florida youth circuit.
Private Tampa Bay · Naples · est. 1964
Founded 1964 on the Gordon River in Naples, this is the city's sailing-leaning private club, distinct from the older Naples Yacht Club a few blocks south. FCYC member with a marina and member-only access to Gordon Pass.
Private Tampa Bay · Naples
Member-owned equity club on its own island at Wiggins Pass, north Naples, with 190 marina slips and direct Gulf access via the pass.
Bareboat, crewed, daysail, and membership charters: sail without owning. Rent a boat you sail yourself in Naples from Island Sailing and Sailboats Unlimited. All Florida sailboat rentals → See all Florida charter companies →
Featured Daysail Tampa Bay · Naples
Naples's longest-running sailing catamaran by its own account, a 53-foot Gold Coast cat carrying 44 passengers from the Naples City Dock since 1991. Daily sunset, shelling and sightseeing seat sails and private charters. The company's Sweet Tiki is a motor boat.
Daysail Tampa Bay · Naples
Champagne sunset and daytime dolphin sails by the seat aboard Cool Beans, a Coast Guard-inspected 42-foot sailing catamaran for 20, from the dock at Osteria Capri on the Isles of Capri, plus private charters. The sister Lil' Beans is a pontoon; the shelling runs go under power.
Tampa Bay · Naples
Island Dreams, a 31-foot Catalina, goes out bareboat by the half day, full day or night from the Naples City Dock, with a checkout sail in place of a certificate. Captained charters for six as well, and a members-only club that sells sailing in blocks of days.
Daysail Tampa Bay · Naples
A 48-foot catamaran built to a Kurt Hughes design, carrying up to 48 from Port O Call Marina on Naples Bay. Narrated shelling, sightseeing and sunset trips daily, year-round, sailing into the Gulf when the weather allows. Private charters too. Sister boat to the Naples Princess.
Tampa Bay · Naples
Naples City Dock operation running since 1985. Public and private sails on Danmark, a 40-foot sloop the company says is the only Coast Guard inspected sloop in Southwest Florida, plus bareboat rental of a smaller Beneteau by the half day or the week.
Crewed Tampa Bay · Naples
One captain, one boat, every trip. Jeff Gage runs private charters for up to six from the Naples City Dock aboard Sea Suite, his 2011 Leopard 39 catamaran, the route set by the guests. Sunset sails, days on the Gulf, afternoons at anchor, and informal instruction on request.
The closest other metros we cover.
Looking wider than Naples? See everything in Tampa Bay & the Gulf Coast, or browse all Florida sailing schools, yacht clubs, and charter companies.
