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Big, forgiving bays with steady afternoons. St. Pete, Sarasota, and Punta Gorda anchor a Gulf-side scene heavy on club racing and shoal-draft cruising.
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Regattas, race series, and championships hosted by clubs and schools across Tampa Bay.
Davis Island Yacht Club · Details at diyc.org ↗
Women's dinghy regatta hosted by DIYC's Dinghy Dames on Hillsborough Bay.
Boca Ciega Learn to Race Sunfish Clinic and Regatta
Boca Ciega Yacht Club · Details at sunfishclass.org ↗
Open ISCA clinic and regatta run by the club's Sunfish Fleet 756 from the Gulfport small-boat launch, with practice racing and drills on Friday and Saturday and the regatta on Sunday.
Davis Island Yacht Club · Details at diyc.org ↗
DIYC Boat of the Year keelboat regatta on Hillsborough Bay.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
First of the Squadron's three Fall Trident series regattas on Sarasota Bay, open to one-design dinghy, multihull and PHRF fleets; run by the Flying Scot fleet.
Star Class North American Championship
Davis Island Yacht Club · Details at diyc.org ↗
Star class continental championship hosted by DIYC on Hillsborough Bay.
A-Class Catamaran Admiral's Cup
Davis Island Yacht Club · Details at regattanetwork.com ↗
Pre-Worlds regatta for the A-Class catamaran fleet, hosted by DIYC on Hillsborough Bay.
U.S. Windsurfer National Championships
Clearwater Community Sailing Center · Details at regattanetwork.com ↗
National championship of the Windsurfer LT one-design, raced in Clearwater Harbor off the center's beach; notice of race and entry on Regatta Network.
A-Class Catamaran World Championship
Davis Island Yacht Club · Details at regattanetwork.com ↗
World championship of the A-Class catamaran, hosted by DIYC in Tampa.
Davis Island Yacht Club · Details at regattanetwork.com ↗
Women's regatta on Hillsborough Bay for women skippers and crews, with PHRF and Portsmouth divisions sailing pursuit starts.
St. Petersburg Yacht Club · Details at yachtscoring.com ↗
Roughly 60-mile random-leg race for spinnaker, racer/cruiser, cruiser, double-handed and multihull classes; an SPYC Boat of the Year and Ocean Racing Series event.
Englewood Sailing Association · Details at regattanetwork.com ↗
One-day youth regatta on Lemon Bay off Indian Mound Park for sailors under 19. Optimist Green and RWB, ILCA 4 and 6, Pico, RS Quest and RS Zest. Sailed each November since 2022.
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.
Jeff Penfield Memorial Regatta
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
Flying Scot class regatta on Sarasota Bay, five races scheduled over the weekend.
Clearwater Community Sailing Center · Details at sailclearwater.org ↗
Six-day Optimist clinic with a team of international coaches, for intermediate and advanced sailors, ending in a regatta on Clearwater Harbor. Second running.
J/70 Mixed-Plus US National Championship
St. Petersburg Yacht Club · Details at j70class.com ↗
National championship for J/70 mixed-crew (Mixed Plus) teams, hosted by SPYC on Tampa Bay.
Davis Island Yacht Club · Details at regattanetwork.com ↗
PHRF distance race first sailed in 1935, from DIYC around Egmont Key and back (63 nm), with a 35 nm short course inside the Skyway. A Suncoast and DIYC Boat of the Year event.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
Second Fall Trident series regatta on Sarasota Bay for dinghy, multihull and PHRF fleets, run by Sunfish Fleet 154.
Tampa Yacht & Country Club · Details at regattanetwork.com ↗
Green Fleet Optimist youth regatta on Hillsborough Bay with daytime racing both days and a Saturday-night glow-decorated race, hosted by TYCC.
Davis Island Yacht Club · Details at diyc.org ↗
Club regatta on Hillsborough Bay.
Davis Island Yacht Club · Details at j70class.com ↗
Opening event of DIYC's J/70 winter series on Hillsborough Bay.
High School Keelboat Nationals
St. Petersburg Yacht Club · Details at spyc.org ↗
National championship for high-school keelboat sailing, raced in J/70s on Tampa Bay.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
Third and last Fall Trident series regatta on Sarasota Bay for dinghy, multihull and PHRF fleets, run by the Luffing Lassies.
Tampa Sailing Squadron · Details at tampasailingsquadron.com ↗
One-design dinghy and small-boat racing on Tampa Bay at Apollo Beach.
Davis Island Yacht Club · Details at diyc.org ↗
DIYC Boat of the Year keelboat regatta on Hillsborough Bay.
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.
Davis Island Yacht Club · Details at j70class.com ↗
Second event of DIYC's J/70 winter series on Hillsborough Bay.
St. Petersburg Yacht Club · Details at yachtscoring.com ↗
Two-day January regatta on Tampa Bay hosted by St. Petersburg Yacht Club.
St. Petersburg Yacht Club · Details at spyc.org ↗
Team-race regatta for senior helms, part of SPYC's winter one-design calendar.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
Opening event of the Squadron's Viper 640 winter series on Sarasota Bay.
Tampa Yacht & Country Club · Details at regattanetwork.com ↗
Youth regatta off Ballast Point for Opti, Open Skiff, ILCA and 420 fleets, hosted by TYCC each January.
St. Petersburg Yacht Club · Details at spyc.org ↗
Selection trials for Lightning-class Pan American Games berths, hosted by SPYC on Tampa Bay.
Davis Island Yacht Club · Details at diyc.org ↗
DIYC Boat of the Year keelboat regatta on Hillsborough Bay.
Platinum Point Yacht Club · Details at ppycbsm.org ↗
The club's annual two-day regatta on Charlotte Harbor, dates supplied by the club's principal race officer.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
First of the three Spring Blossom series regattas on Sarasota Bay for dinghy, multihull and PHRF fleets, run by the Viper and Laser fleets.
Davis Island Yacht Club · Details at diyc.org ↗
Regatta for the singlehanded 2.4mR keelboat class on Hillsborough Bay.
Flying Scot Florida District 5 Regatta
Davis Island Yacht Club · Details at fssa.com ↗
Flying Scot Florida District 5 event for the 2026-27 circuit, sailed on Hillsborough Bay.
Platinum Point Yacht Club · Details at ppycbsm.org ↗
Long-distance race down Charlotte Harbor to Useppa Island, on the club's published 2026-27 schedule.
John Jennings Memorial Regatta
St. Petersburg Yacht Club · Details at spyc.org ↗
One-day memorial regatta on Tampa Bay honoring the longtime SPYC sailor and race official.
Davis Island Yacht Club · Details at j70class.com ↗
Final event of DIYC's J/70 winter series on Hillsborough Bay.
St. Petersburg Yacht Club · Details at spyc.org ↗
Two-day February regatta on Tampa Bay hosted by St. Petersburg Yacht Club.
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.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
Second event of the Squadron's Viper 640 winter series on Sarasota Bay.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
Second Spring Blossom series regatta on Sarasota Bay for dinghy, multihull and PHRF fleets, run by the E Scow and multihull fleets.
L30 Double Handed North American Championship
St. Petersburg Yacht Club · Details at spyc.org ↗
Double-handed North American championship for the L30 class on Tampa Bay.
Helly Hansen Sailing World Regatta Series (Melges 24 Midwinters)
St. Petersburg Yacht Club · Details at spyc.org ↗
National one-design and offshore circuit stop hosted by SPYC; doubles as the Melges 24 Midwinter Championship.
St. Petersburg Yacht Club · Details at spyc.org ↗
Midwinter championship of the ILCA (Laser) class East circuit, hosted by SPYC on Tampa Bay.
Sarasota Bay Multihull Regatta
Sarasota Sailing Squadron · Details at sarasotasailingsquadron.org ↗
Multi-day multihull regatta hosted by the Squadron on Sarasota Bay.
Davis Island Yacht Club · Details at diyc.org ↗
DIYC Boat of the Year race on Hillsborough Bay.
Platinum Point Yacht Club · Details at ppycbsm.org ↗
Long-distance club race on Charlotte Harbor, on the published 2026-27 schedule.
USSCA Florida Regional Championship I
Boca Ciega Yacht Club · Details at sunfishclass.org ↗
First of the two Sunfish Florida regional championships and a qualifier for the ISCA Worlds, hosted on Boca Ciega Bay by the Boca Ciega Yacht Club Foundation.
Tampa Sailing Squadron · Details at tampasailingsquadron.com ↗
Gasparilla-season regatta on Tampa Bay, hosted by Tampa Sailing Squadron.
Dunedin Boat Club · Details at dunedinboatclub.org ↗
Gulf distance race co-hosted with Clearwater Yacht Club, a Gulf Region Boat of the Year stop.
Davis Island Yacht Club · Details at diyc.org ↗
South Atlantic Interscholastic Sailing Association high school regatta hosted at DIYC.
St. Petersburg Yacht Club · Details at spyc.org ↗
One-day regatta sailed out of SPYC's Pass-a-Grille station on Boca Ciega Bay.
St. Petersburg Yacht Club · Details at spyc.org ↗
One-day regatta sailed out of SPYC's Pass-a-Grille station, the day after the Pennington Cup.
62nd Dinghy Championship / Fireball & Friends Regatta
Davis Island Yacht Club · Details at diyc.org ↗
Dinghy championship weekend sailed with the Fireball fleet and invited classes on Hillsborough Bay.
Davis Island Yacht Club · Details at diyc.org ↗
DIYC Boat of the Year distance race from Davis Island to St. Petersburg Yacht Club.
Dunedin Boat Club · Details at dunedinboatclub.org ↗
The club's annual Boat of the Year regatta on the Gulf off Dunedin, moved from its former May slot to March for 2027.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
Final event of the Squadron's Viper 640 winter series on Sarasota Bay.
Sarasota Sailing Squadron · Details at regattanetwork.com ↗
Third Spring Blossom series regatta on Sarasota Bay for dinghy, multihull and PHRF fleets, run by the Melges 15 and monohull fleets.
Clearwater Yacht Club · Details at dunedinboatclub.org ↗
CYC's annual Gulf race and a Gulf Region Boat of the Year stop, dated on partner Dunedin Boat Club's public calendar because CYC's own calendar is members-only.
Platinum Point Yacht Club · Details at ppycbsm.org ↗
Season-closing long-distance race on Charlotte Harbor, dates supplied by the club's principal race officer.
Thistle Midwinters East Championship
Davis Island Yacht Club · Details at diyc.org ↗
Thistle class midwinters east championship hosted by DIYC on Hillsborough Bay.
St. Petersburg Yacht Club · Details at spyc.org ↗
Lightning-class winter championship on Tampa Bay in the run-up to the class world championship.
Sarasota Sailing Squadron · Details at sarasotasailingsquadron.org ↗
E Scow class midwinter championship on Sarasota Bay; practice race on the opening day.
Isles Yacht Club · Details at islesyc.com ↗
The IYC Sailing Club's open Harbor 20 charity regatta on Charlotte Harbor, on the fleet's final 2026-27 schedule.
Tampa Sailing Squadron · Details at tampasailingsquadron.com ↗
Invitational midwinter regatta on Tampa Bay out of Apollo Beach.
Venice Sailing Squadron, Venice Yacht Club · Details at venicesailingsquadron.org ↗
Two-day regatta off Venice, co-hosted by the Venice Sailing Squadron and Venice Yacht Club.
St. Petersburg Yacht Club · Details at spyc.org ↗
World championship of the Lightning class, hosted by SPYC on Tampa Bay.
Sarasota Sailing Squadron · Details at sarasotasailingsquadron.org ↗
Spring invitational regatta weekend at the Sarasota Sailing Squadron.
Davis Island Yacht Club · Details at diyc.org ↗
DIYC Boat of the Year keelboat regatta on Hillsborough Bay.
Bird Key Yacht Club · Details at sarasotasailingsquadron.org ↗
Bird Key Yacht Club's annual regatta on Sarasota Bay, listed on the Sarasota Sailing Squadron's 2026–27 regatta schedule.
Sarasota Sailing Squadron · Details at sarasotasailingsquadron.org ↗
Melges 15 fleet regatta on Sarasota Bay.
Davis Island Yacht Club · Details at diyc.org ↗
South Atlantic Interscholastic Sailing Association NIT championship hosted at DIYC.
Margarita Madness Ladies Regatta
Tampa Sailing Squadron · Details at tampasailingsquadron.com ↗
Women's one-day regatta on Tampa Bay out of Apollo Beach.
Davis Island Yacht Club · Details at diyc.org ↗
Women's dinghy regatta hosted by DIYC's Dinghy Dames on Hillsborough Bay.
TSS Tampa Bay Sea Scout Regatta
Tampa Sailing Squadron · Details at tampasailingsquadron.com ↗
Sea Scout camporee and regatta at the TSS clubhouse, with pierside competition and sailing on Tampa Bay; club members skipper the boats.
St. Petersburg Yacht Club · Details at spyc.org ↗
Two-day spring race weekend on Tampa Bay hosted by St. Petersburg Yacht Club.
The Ocean Race: St. Petersburg Stopover
St. Petersburg Yacht Club · Details at spyc.org ↗
The round-the-world Ocean Race calls at St. Petersburg, per SPYC's 2026–27 regatta schedule.
Davis Island Yacht Club · Details at diyc.org ↗
Distance race from Davis Island to Venice on Florida's Gulf coast.
Davis Island Yacht Club · Details at diyc.org ↗
Multi-day distance race hosted by DIYC out of Hillsborough Bay.
St. Petersburg Yacht Club · Details at yachtscoring.com ↗
Offshore race from the St. Petersburg Pier across the Gulf to Pensacola Bay, co-hosted with Pensacola Yacht Club; the cruiser class starts a day early.
Tampa Sailing Squadron · Details at tampasailingsquadron.com ↗
Tampa Sailing Squadron's season-closing regatta on Tampa Bay out of Apollo Beach.
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 →
ASA and US Sailing certifications, plus introductory programs. See all Florida schools →
Tampa Bay · St. Petersburg
Small instructor-led NauticEd school headquartered in St. Petersburg, teaching on the student's own boat or wherever a traveling engagement takes it. Certify through Bareboat Charter Master and the SLC license, then apply it on the school's week-long international flotillas.
Tampa Bay · St. Petersburg
St. Petersburg school specializing in private one-on-one instruction on a young, well-kept fleet. Covers the ASA pathway from beginner keelboat through advanced cruising and the docking endorsement.
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.
Tampa Bay · St. Petersburg
Private NauticEd instruction on Tampa Bay from the St. Petersburg Municipal Marina, on school boats or your own. Runs the full rank ladder through Bareboat Charter Master and the SLC international license, taught by a two-time American Sailing Instructor of the Year.
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 · Sarasota
Dual ASA sail and US Powerboating school serving Sarasota, Bradenton, and Tampa Bay, with boats based at Regatta Pointe Marina in Palmetto. Classes cap at four, on a fleet from a 13-foot dinghy to a Catalina 36, or aboard your own boat.
Tampa Bay · Longboat Key
ASA-affiliated school on Longboat Key overlooking Sarasota Bay, running the full Learn-to-Sail pathway through bareboat and catamaran cruising for nearly 20 years. Captained charters and rentals on the bay and Gulf.
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.
Tampa Bay · Punta Gorda
Year-round ASA instruction out of Burnt Store Marina on Charlotte Harbor. Private lessons, small-group sessions (up to four), or family classes on a fleet of 30–45-foot cruising sailboats.
Tampa Bay · Punta Gorda
Volunteer-run nonprofit teaching sailing from Punta Gorda's Bayfront Center on Charlotte Harbor since 2015. Adult private lessons taught by US Sailing-certified instructors on a dinghy fleet, plus summer youth camps with scholarships so cost is never the gate.
Tampa Bay · Punta Gorda
Charlotte Harbor ASA school running the full pathway from Basic Keelboat through Advanced Coastal on an unsinkable Etap 32, with liveaboard 104 and 106 courses, and a Mediterranean branch in Greece whose flotillas have run since 2009.
Tampa Bay · North Fort Myers
US Sailing-affiliated nonprofit on the Caloosahatchee River, running youth dinghy programs (ages 5–18) on Optimists, ILCAs, and C420s since 1983, plus US Sailing Basic Keelboat instruction.
Tampa Bay · Cape Coral
Liveaboard ASA school teaching from Tarpon Point Marina in Cape Coral since 1984, on the fleet it shares with sister charter operator Southwest Florida Yachts. Courses from Basic Sailing through Advanced Coastal Cruising run two to ten days aboard on Pine Island Sound.
Tampa Bay · Fort Myers Beach
ASA school and charter operation sailing from the Fort Myers Beach mooring field on a 45-foot Jeanneau. Liveaboard courses of two to seven days on the Sanibel and Fort Myers Beach waters, with combo packages through the bareboat certificate.
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Member-driven yacht clubs and community sailing centers. See all Florida clubs →
Featured Private Tampa Bay · Tampa
Member-owned private club at the south end of Davis Islands in Hillsborough Bay. Long-standing Thursday Night Races open to anyone, plus a robust junior program through the Davis Island Youth Sailing Foundation.
Featured Community Tampa Bay · St. Petersburg
City-owned sailing center at Demens Landing, operated under agreement with the St. Petersburg Yacht Club. Hosts youth and adult programs, adaptive sailing initiatives, and regional regattas, the city's public-access counterpart to SPYC.
Featured Private Tampa Bay · St. Petersburg · est. 1909
Founded 1909. Hosts the St. Petersburg stop of the Sailing World Regatta Series and anchors one of the deepest one-design and offshore racing scenes on the Gulf Coast. Mediterranean Revival clubhouse on the National Register of Historic Places.
Private Tampa Bay · Gulfport
Welcoming, affordable sailing club on Boca Ciega Bay in Gulfport, four miles from the Gulf: cruising, one-design and handicap racing, Sea Scouts, and a well-known basic sail school on a fleet of Catalina 16.5s.
Private Tampa Bay · Clearwater Beach · est. 1934
Founded 1934 at the north end of Clearwater Beach, on the Gulf and Mandalay Channel. Member-owned beach and yacht club with a clubhouse, marina, and small private beach.
Community Tampa Bay · Clearwater
Nonprofit public sailing center on Sand Key, launching from its own beach on Clearwater Harbor: more than fifty boats for hourly rental or unlimited member use, hourly lessons, a ten-week summer camp, Optimist, 420 and windsurfing race teams, and the regattas it hosts.
Private Tampa Bay · Clearwater Beach · est. 1911
Chartered February 1911, one of the original thirteen member clubs of the Florida Council of Yacht Clubs. Bayway Boulevard clubhouse on Clearwater Beach with deep Gulf Coast racing roots.
Private Tampa Bay · Dunedin · est. 1929
Volunteer-run boating club formed 1929 at the Dunedin Municipal Marina on St. Joseph Sound. Races the Gulf Races and Bay Twilight series under West Florida PHRF ratings and sails in the Gulf Region Boat of the Year rotation alongside Clearwater Yacht Club.
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Private Tampa Bay · Tampa · est. 1904
Founded 1904 by Tampa's leading business and professional men. Fourteen-acre clubhouse on the western shore of Hillsborough Bay just south of Ballast Point Pier; ~1,400 members make it one of the larger private clubs in the FCYC network.
Private Tampa Bay · Tarpon Springs · est. 1949
Founded April 1949 by Tarpon Springs boaters and civic leaders; clubhouse and docks built 1954 alongside the club's incorporation. North Pinellas private club at the upper end of Florida's Gulf Coast.
Private Tampa Bay · Sarasota
Private bay-front club on Bird Key in Sarasota. The clubhouse was demolished in fall 2025 and is being rebuilt on the same footprint, raised to meet FEMA standards; the club expects to open it in December 2026. Marina and tennis courts stay open to members and reciprocal guests.
Private Tampa Bay · Palmetto · est. 1946
Chartered in 1946 by 18 Manatee River boating enthusiasts. Now ~600 families across Snead Island, with a waterfront clubhouse and one of the larger member rosters on the upper Tampa Bay coast.
Community Tampa Bay · Sarasota · est. 1947
Community sailing club on the widest part of Sarasota Bay. Grew out of the Sarasota Yacht Club's youth program in the late 1930s by sailors who couldn't afford the YC dues; chartered independently 1947 after a wartime hiatus.
Private Tampa Bay · Sarasota · est. 1926
Incorporated 1926, founded around Fish class inter-club racing. Sits inside Big Pass on Sarasota Bay with an annual SYC Invitational Regatta running since 1979. Members-only learn-to-sail programs for all ages.
Community Tampa Bay · Venice · est. 1973
Founded 1973. Volunteer-run club of about ninety memberships and no clubhouse. Saturday buoy and distance racing off Venice and Nokomis, October to May, Gulf-coast cruises, and the Windjammer and Sharks Tooth regattas organized with Venice Yacht Club. Boat ownership optional.
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Private Tampa Bay · Venice · est. 1951
Founded 1951 at Tarpon Center on Roberts Bay, Venice. The Venice Youth Boating Association, a non-profit founded at the club in 1952, runs summer camps, after-school programs, and competitive sailing teams alongside the parent club's calendar.
Private Tampa Bay · Port Charlotte · est. 1973
FCYC member club founded 1973 on a five-acre property overlooking Charlotte Harbor; clubhouse broke ground September 1974. Compact private club with the harbor's broad shoal-draft cruising grounds at the dock.
Community Tampa Bay · Englewood · est. 2002
Volunteer-run youth and community sailing on Lemon Bay from Indian Mound Park, founded 2002 out of the Lemon Bay Rag Haulers. Summer camps and Saturday sailing for ages 9 to 17, a four-day adult intro course, an ILCA youth race team, and the Lemon Drop Regatta each November.
Private Tampa Bay · Punta Gorda
Private dining and social club on Charlotte Harbor in Punta Gorda. FCYC member with a marina at the head of the harbor, the city's other yacht club alongside Charlotte Harbor YC.
Private Tampa Bay · Punta Gorda · est. 1984
Founded 1984 by Burnt Store Marina boaters and named for the spit between the marina's two basins. Winter Monday keelboat racing on Charlotte Harbor plus the Golden Conch Regatta each January, open to all area racers; hosted the 1991-92 Olympic Soling trials.
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Private Tampa Bay · Captiva
Private club on the Gulf side of Captiva Island, between Pine Island Sound and the open Gulf. FCYC member with about 500 members, most of them Captiva and Sanibel residents, and a working dock for cruising members crossing between Charlotte Harbor and the Ten Thousand Islands.
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.
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Private Tampa Bay · Marco Island
Private FCYC member club just across the S.S. Jolley Bridge on Marco Island, looking out over the Marco River and Smokehouse Bay. Cruising-and-social calendar with a working marina at the heart of it.
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.
Private Tampa Bay · Fort Myers · est. 1947
Founded 1947 on the Caloosahatchee in downtown Fort Myers. A private yacht club for boaters and non-boaters with 70+ years of cruising and shared-passion calendar. Distinct from the unrelated Royal Palm YC in Boca Raton.
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Private Tampa Bay · Fort Myers · est. 1990
FCYC private club inside the gated St. Charles Harbour community on the south side of the Caloosahatchee, near the Sanibel Causeway. Working marina, dining room, and an active reciprocal-club calendar.
Private Tampa Bay · New Port Richey · est. 1965
Chartered 1965 on the Gulf Harbors North Channel in New Port Richey; neither boat ownership nor neighborhood residency is required. Runs a PHRF regatta series on 6-to-10-mile courses off Anclote Key, a youth sailing camp, adult sailing classes, and transient slips.
Private Tampa Bay · Apollo Beach
Member-owned sailing club on Tampa Bay at Apollo Beach: regattas and cruising on the bay, learn-to-sail for ages seven and up, a youth program and Sea Scouts, plus wet and dry slips for members.
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Bareboat, crewed, daysail, and membership charters: sail without owning. Rent a boat you sail yourself in Bradenton Beach, Cape Coral, Captiva, Fort Myers Beach, Naples, and Sarasota. All Florida sailboat rentals → See all Florida charter companies →
Crewed Tampa Bay · Dunedin
Daily captained sails from the Dunedin Marina aboard Miracle, a 41-foot Morgan Out Island skippered by Captain Herman. Sunset and dolphin cruises and full days at the barrier islands. A separate business from Wind Star Sailing, which keeps a similar Morgan at the same marina.
Daysail Tampa Bay · Clearwater Beach
A 52-foot steel staysail schooner built in Clearwater in 2016, sailing daily from the Clearwater Beach Municipal Marina. Two-hour afternoon and sunset sails by the seat, 22 guests at most, plus private charters. The course follows the wind, and guests can help raise sail.
Crewed Tampa Bay · St. Petersburg
Captained sails on Tampa Bay from the Harborage Marina, run by a couple who cruised the Caribbean aboard the boat that is now the fleet's flagship. Three boats, a Morgan 44, a Catalina 355 and a Leopard 45 catamaran, out for one to four hours with six aboard.
Daysail Tampa Bay · Treasure Island
Gaff-rigged topsail schooner sailing from Treasure Island out through John's Pass into the Gulf. Suncoast Horizon is 55 feet, built in 2000 to a Merritt Walter design, certified for 28 guests and held to about 21. Sunset and day sails by the seat, plus private charters.
Crewed Tampa Bay · St. Petersburg
Sweet Escape is a 2023 Bali 4.2 catamaran running private all-inclusive charters for up to six on Tampa Bay out of St. Petersburg. Captain and first mate, paddleboards, kayaks, snorkelling gear and refreshments come with every booking. Sunset, swim and full-day sails.
Daysail Tampa Bay · St. Petersburg
Between boats. Hawkeye, the 47-foot sailboat behind these two-hour sunset sails from downtown St. Petersburg, was sold in June 2026, and the sails are on hold until the company finds another vessel.
Crewed Tampa Bay · Gulfport
Private sails for up to six on Boca Ciega Bay and Tampa Bay from the Gulfport waterfront aboard Cay Michele, a 1981 Hardin Voyager 45 staysail ketch, hull 92 of the 130 built. Sunset sails, barrier-island runs with a dinghy ashore, and sandbar afternoons, every trip yours alone.
Crewed Tampa Bay · Dunedin
Wind Star is a 41-foot Morgan Out Island ketch at slip 8 in the Dunedin Marina, with Captain Harry at the helm. Half days on St. Joseph Sound, full days to Anclote Key or Three Rooker Bar, sunset and dolphin cruises, and overnight to week-long charters for up to four.
Tampa Bay · Bradenton Beach
Gulf-front beach rental on Anna Maria Island, family run for forty years and, by its own account, the only place on the island renting sailboats. Hobie Wave and Hobie Getaway catamarans by the hour or half day, first come, first served, with a short lesson for first-timers.
Daysail Tampa Bay · Holmes Beach
Capt. Kit Baxter sails Flip Flops, a Maine Cat 30 catamaran, out of Holmes Beach on Anna Maria Island, six guests at most. Public sails go with two aboard, private sails need three spots. Sunset and day sails on the bay, and four- to six-hour runs to Passage Key and Egmont Key.
Daysail Tampa Bay · Sarasota
Three 30-foot sailing catamarans, two Maine Cat 30s and a Stiletto 30, on Sarasota Bay and the Gulf passes since 2007. Public seat sails from Marina Plaza downtown, private charters from there or Longboat Key, and custom six-hour days out of Holmes Beach on Anna Maria Island.
Tampa Bay · Sarasota
One-boat bareboat operation at Sara Bay Marina, renting a Catalina 30 by the half day, the day or the week on Sarasota Bay. No certificate is asked for. The bar is experience instead, extensive for a day charter and two recent years to take her overnight, and renters must be 25.
Daysail Tampa Bay · Venice
Two-hour sails into the Gulf from the Crow's Nest Marina at the Venice jetties aboard Inspiration, with Captain Dove and mate Tim. Six passengers at most, by appointment, guests welcome at the wheel. Hauled out for maintenance July 14 to October 15, 2026, per the operator.
Featured 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.
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.
Daysail Tampa Bay · Fort Myers Beach
Copacetic is a 36-foot sailing catamaran her captain spent years building by hand in Fort Myers, now carrying 24 guests off Fort Myers Beach and Sanibel. Day and sunset sails by the seat, a Saturday yoga sail, and private charters to Lovers Key and Upper Captiva.
Crewed Tampa Bay · Goodland
Easy Breezy, a 30-foot Stiletto sailing catamaran, launched from the Goodland Boat Park ramp on the Ten Thousand Islands side of Marco Island, Nick Rezac at the tiller. Private two-hour, half-day and full-day sails and a sunset cruise for up to six, with an island stop.
Tampa Bay · Fort Myers Beach
The same Fort Myers Beach family has run the beach stands at the Diamond Head and Best Western resorts on Estero Boulevard since 1991, and the Hobie 14s and 16s go off the sand there by the hour, booked online, with safety gear and a short orientation included.
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 · Fort Myers Beach
Husband-and-wife operation sailing Orion's Child, a 2004 Hunter 386 monohull, from slip C-18 at Salty Sam's Marina on Fort Myers Beach since 2009. Sunset sails and daytime trips into the Gulf off Fort Myers Beach and Sanibel, six guests at most, sold private or by the seat.
Crewed Tampa Bay · Marco Island
Mariah is a 40-foot catamaran at Riverside Marina on the Marco Island Yacht Club property, and Captain Ron sails her one group at a time. Private day sails and sunset cruises for up to six, about three hours on the Gulf off Marco, with fifty years of sailing behind the skipper.
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.
Tampa Bay · Captiva
The one sailboat rental on Sanibel or Captiva as of September 2026. Fourteen-foot Hobie Waves from the shop on Andy Rosse Lane, the Captiva village street that ends on the Gulf beach, by the hour up to a full day and reservable in person, online or by phone.
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