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Sugar-white beaches, Pensacola Bay, and Choctawhatchee: the Gulf's clearest sailing water. Smaller fleets, bigger sandbars, and the kind of harbors where someone always comes by with a tow line.
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Sailing by city: Pensacola Destin & Fort Walton Beach Panama City Tallahassee & Apalachee Bay
Regattas, race series, and championships hosted by clubs and schools across Panhandle.
Pensacola Yacht Club · Details at regattaman.com ↗
GYA West Florida Ocean Racing Circuit regatta: buoy racing Saturday on Pensacola Bay, a distance race to the Gulf sea buoy Sunday.
Fort Walton Yacht Club · Details at fwyc.org ↗
One-day club regatta on Choctawhatchee Bay hosted by Fort Walton Yacht Club.
Pensacola Yacht Club · Details at pensacolayachtclub.org ↗
One-design regatta on Pensacola Bay, run by the club over the Halloween weekend.
Pensacola Beach Yacht Club · Details at regattaman.com ↗
One-day GYA handicap regatta on Pensacola Bay, with the skippers' meeting at the club the evening before.
Pensacola Yacht Club · Details at melges24.com ↗
Melges 24 regatta on Pensacola Bay, a stop on the class North American Sailing Series.
Fort Walton Yacht Club · Details at fwyc.org ↗
One-day November regatta on Choctawhatchee Bay hosted by Fort Walton Yacht Club.
Gobbler Regatta and Leftover Feast
Apalachee Bay Yacht Club · Details at abyconline.org ↗
Post-Thanksgiving club regatta on Apalachee Bay off Shell Point, followed by a leftovers potluck at the clubhouse.
Pensacola Yacht Club · Details at pensacolayachtclub.org ↗
The club's December one-day regatta on Pensacola Bay, sailed in ORR-EZ handicap and one-design classes.
Apalachee Bay Yacht Club · Details at abyconline.org ↗
New Year's Day club regatta on Apalachee Bay, run by the ABYC vice commodore.
ISCA Midwinters Series (Sunfish)
Pensacola Yacht Club · Details at sunfishclass.org ↗
Weeklong Sunfish class midwinters series on Pensacola Bay, a World Championship qualifier.
Flying Scot Midwinter Championship
Pensacola Yacht Club · Details at fssa.com ↗
National Flying Scot Sailing Association Midwinters, hosted by PYC on Pensacola Bay.
Stephen C. Smith Memorial Regatta
Apalachee Bay Yacht Club · Details at abyconline.org ↗
ABYC's annual spring regatta on Apalachee Bay off Shell Point, sailed over a Friday to Sunday.
Pensacola Yacht Club · Details at yachtscoring.com ↗
Offshore race from St. Petersburg across the Gulf to Pensacola Bay, co-hosted with St. Petersburg Yacht Club; PYC hosts the finish, the post-race party and the awards.
Live wind and sky, spot by spot, straight from the National Weather Service. Each card opens the full point forecast. NWS Mobile marine forecast (Pensacola–Apalachicola) →
ASA and US Sailing certifications, plus introductory programs. See all Florida schools →
Panhandle · Gulf Breeze
Pensacola Beach school built around live-aboard ASA classes for couples, families, and small groups, with extended at-sea time and the full coastal-cruising pathway.
Panhandle · Pensacola Beach
One-captain ASA school and charter operation at Sabine Marina on Pensacola Beach, teaching private lessons capped at two students aboard a 32-foot J Boat. No-test leisure lessons for vacationers alongside the full certification track.
Panhandle · Niceville
ASA school, charter, and rental operation at Bluewater Bay Marina on the north shore of Choctawhatchee Bay. J/80s for the fundamentals, cruisers to a Jeanneau 389 for the liveaboard courses, and a founder with a run of ASA Outstanding Instructor awards.
Panhandle · Pensacola
Downtown Pensacola ASA school at Seville Harbour Marina, teaching since 2001 with a roster of USCG-licensed captains. Capri 22s for the fundamentals; the cruising courses run as multi-night liveaboards on a Beneteau 393, meals and bunks included.
Panhandle · Panama City
St. Andrews Bay-based ASA school next door to Panama City's City Marina. Instructors with 70+ combined years on the water, classroom plus extended on-water time on boats from a 25-foot trainer to cruising catamarans.
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Member-driven yacht clubs and community sailing centers. See all Florida clubs →
Featured Private Panhandle · Pensacola · est. 1908
Originally organized 1908 as the Pensacola Yacht and Motor Boat Club; chartered 1910. Charter member of the Gulf Yachting Association and a US Sailing affiliate. Deep junior fleet with Optimists, 470s, Lasers, and catamarans.
Private Panhandle · Crawfordville · est. 1969
Big Bend sailing club off Shell Point, organized in 1969 by sailboat racers. Cruising and buoy racing on Apalachee Bay, the annual Stephen C. Smith Memorial Regatta, and youth sailing through Apalachee Bay Community Sailing.
Private Panhandle · Panama City Beach · est. 1986
Private nonprofit yacht club chartered 1986 along the Gulf Coast in the Bay Point community at the Marriott Resort, Panama City Beach. ~200 members; calendar weighted toward cruising and social events rather than active racing.
Community Panhandle · Fort Walton Beach · est. 1992
US Sailing certified Community Sailing Center, a 501(c)(3) founded 1992, running youth camps, race teams, and four high-school sailing programs on Choctawhatchee Bay out of Fort Walton Yacht Club. Open to the public, program-fee based, with scholarships.
Private Panhandle · Fort Walton Beach · est. 1951
Founded 1951 on the western shore of Choctawhatchee Bay. FCYC member club with a working volunteer culture and a calendar that mixes social events, family activities, and Gulf-side sailing.
Private Panhandle · Pensacola Beach · est. 1980
Sailing club at the entrance to Pensacola Beach, upstairs at 655 Pensacola Beach Blvd overlooking Little Sabine Bay; first commodore elected 1980. Gulf Yachting Association and US Sailing member; boat ownership is not required to join.
View details →
Private Panhandle · Panama City
Panama City's private sailing club on St. Andrews Bay, also known as the Panama City Yacht & Sailing Club. The historic clubhouse was lost to a 2023 fire; rebuilding is underway, with bay racing continuing throughout.
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Bareboat, crewed, daysail, and membership charters: sail without owning. Rent a boat you sail yourself in Navarre Beach, Niceville, Panama City, Panama City Beach, and Pensacola Beach. All Florida sailboat rentals → See all Florida charter companies →
Daysail Panhandle · Pensacola Beach
Two-hour sails from Pier One Marina on Pensacola Beach aboard Dare II, a Condor 40 trimaran, one of twenty-one built in Annapolis from 1985 to 1991. Daily 11am and 2pm sails and a sunset cruise, six guests at most, booked online. Captain Kirk has owned her since 2002.
Crewed Panhandle · Fort Walton Beach
No trips for the rest of 2026 after hurricane damage in the area; the owners plan to resume in March 2027. Private crewed catamaran daysails on a Stiletto 27 from Adventure Marina on Okaloosa Island, with Crab Island, sunset and snorkel runs for up to six guests.
Crewed Panhandle · Destin
Space Dancer, a 45-foot Beneteau sloop, leaves the AJ's Seafood and Oyster Bar dock on Destin Harbor, then out East Pass into the Gulf with Captain Chris. Two- to four-hour private sails, sunset and fireworks cruises, time at the helm on request, and overnight trips year round.
Daysail Panhandle · Panama City Beach
Two sailing catamarans, the 50-foot Island Time and the 53-foot Island Time II, out of Grand Lagoon in Panama City Beach. A three-hour snorkel sail to Shell Island with gear and paddleboards aboard, and a two-hour sunset dolphin sail, both sold by the seat.
Daysail Panhandle · Pensacola Beach
Jolly Mon is a 27-foot American Mariner sloop, the boat this Pensacola Beach family business started with in 2011 and still its only sailboat. Two- to four-hour sailing, snorkelling and sunset tours from Pier One Marina. The rest of the Jolly fleet is powered tritoons.
Panhandle · Pensacola Beach
Pensacola Beach watersports operation on Santa Rosa Sound, in business for more than fifty years. Hobie Wave and Hobie Getaway beach-cat rentals by the half or full day, first come first served, for sailors who can already sail; pontoons, Sea-Doos and parasailing alongside.
Panhandle · Niceville
Bareboat rentals and crewed sails from Bluewater Bay Marina on Choctawhatchee Bay. J/80s by the day, a Beneteau 331 and a Jeanneau 389 by the day or up to three nights aboard, for skippers with ASA 103 or equivalent; captained sunset, dolphin and Crab Island trips for up to six.
Panhandle · Navarre Beach
Navarre Beach Ski & Sail has launched Hobies from the sand at Juana's Pagodas since 1989. Thirteen-foot Hobie Waves for up to four, sailed on Santa Rosa Sound between Navarre Beach and Pensacola Beach, by the hour. Prior sailing experience is required.
Panhandle · Panama City Beach
Beach concession along Panama City Beach renting 16-foot Hobie Getaways you sail yourself, for up to four, by the hour or the day. Booked by phone, March through October, from a stand that also does chairs, kayaks, pontoons and jet skis.
Daysail Panhandle · Panama City Beach
Daydreams is a 47-foot Beneteau monohull sailing out of Grand Lagoon to Shell Island, six guests on a shared snorkel or sunset sail and twelve on a private charter. The company's Privateer, Footloose, Lazy Daze and tiki boat are all powered, so Daydreams is the one that sails.
Panhandle · Panama City
Bareboat and captained charters on a Vagabond 42 ketch from the CSS Yacht Basin in St. Andrews, Panama City's old waterfront. Rentals go out in four-hour blocks to skippers with ASA 104 or equivalent; the same boat does lessons and captained half and full days for up to six.
Daysail Panhandle · Pensacola
Sirena is a 48-foot sailing catamaran working out of Southwind Marina on Pensacola's south shore, certified for 49 and held to 12. Sunset and dolphin sails, a half-day run to Fort McRee and Johnson Beach, a snorkelling trip, and a Blue Angels practice cruise on flying days.
Crewed Panhandle · Destin
Private charters on the trimaran Nice Tri from Destin Harbor behind the Marina Cafe, run by Capt. Pam. Two-hour scenic sails, snorkelling over the grass flats and the second sandbar, dolphin runs and Crab Island afternoons, with sunset and fireworks cruises in season.
Crewed Panhandle · Pensacola
A 47-foot Leopard catamaran on Pensacola Bay, boarding at the Maritime Park docks downtown. Half- and full-day charters with paddleboards and kayaks aboard, swim calls at Deadman's Island and Fort McRae, an overnight to Orange Beach, and an ASA 114 course on the same boat.
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Keep exploring: Sailing guides Florida events calendar ASA schools Bareboat charters
