Regattas, race series, and championships hosted by clubs and schools across Key Largo & the Upper Keys.
FWC Florida Keys Regional Wave Regatta
Upper Keys Sailing Club · Details at regattanetwork.com ↗
Three-day Hobie Wave regional regatta on Buttonwood Sound, hosted by the club in Key Largo.
Upper Keys Sailing Club · Details at upperkeyssailingclub.com ↗
Week-long A-Class catamaran midwinter regatta off Key Largo, open to fleet sailors from outside the club.
Upper Keys Sailing Club, Mark Sorensen Youth Sailing Program · Details at regattanetwork.com ↗
The Mark Sorensen Youth Sailing Program's regatta, sailed from Rowell's Waterfront Park on Blackwater Sound. Optis, youth ILCAs, Club 420s and windsurfers, ages 8 to 18; 18th running.
Force 5 Midwinter Championship
Upper Keys Sailing Club · Details at force5class.org ↗
Force 5 class midwinter championship off Key Largo, hosted by the club's resident Fleet 50.
Upper Keys Sailing Club · Details at snipeusa.com ↗
SCIRA midwinter regatta for the Snipe class on Buttonwood Sound, the circuit's Florida stop.
Live wind and sky, spot by spot, straight from the National Weather Service. Each card opens the full point forecast. NWS Key West marine forecast →
Learn to sail, ASA and US Sailing certification courses, and private lessons. ASA courses in Key Largo & the Upper Keys are taught by American Sailing Academy, Sunshine Coast Adventures Sailing School, and Veteran Sailing Association. All Florida ASA schools → See all Florida schools →
The Keys · Key Largo
ASA school on Buttonwood Sound, teaching from the Key Lime Sailing Club cottages at mile marker 99. Courses run on demand 363 days a year; stay in a cottage, learn on Florida Bay, and keep sailing the club's Catalina 22s free after you certify.
The Keys · Key Largo
Nonprofit youth sailing program on Buttonwood Sound, sailing from the Upper Keys Sailing Club beach in Key Largo. Summer, fall, spring and homeschool sessions for ages 6 to 18 in Optis, Club 420s and RS dinghies, scholarships, and host of the Buccaneer Blast each February.
The Keys · Tavernier
Upper Keys ASA school running liveaboard course-vacations from Tavernier, with certifications earned on multi-day cruises through the Keys and out to the Bahamas. The owner-instructor is a six-time ASA Outstanding Instructor of the Year.
The Keys · Tavernier
Upper Keys ASA school founded by a Navy SEAL, with a "crawl, walk, run" curriculum built around veterans, their supporters, and couples. Active-duty and honorably discharged military earn their ASA certifications free of charge.
Member-driven yacht clubs and community sailing centers. See all Florida clubs →
Bareboat, crewed, daysail, and membership charters: sail without owning. Rent a boat you sail yourself in Key Largo & the Upper Keys from Calypso Sailing, Key Lime Sailing Club & Cottages, and Scuppers Watersports. All Florida sailboat rentals → See all Florida charter companies →
The Keys · Key Largo
Leopard catamaran fleet working the Keys out of Marina Del Mar in Key Largo since 1988, with further docks in Key West and on Stock Island. Bareboat or captained, by the day, the sunset or overnight, to the Keys and the Bahamas. Bareboat asks for time on a comparable catamaran.
The Keys · Key Largo
Cottage-and-sailboat package on the bayside of Key Largo. Rent a cottage and, if you are a qualified sailor with recent time on the water, the 22-foot Catalina at the dock is yours to sail inside Florida Bay at no charge. Larger boats and captained trips cost extra.
The Keys · Key Largo
Baker's Cay, the resort on the bayside of Key Largo, keeps 14-foot Hobie Waves on its beach through Scuppers, by the hour, briefing and life vest included, open to beginners and old hands alike. The same company runs a second base on St. Pete Beach.
The closest other metros we cover.
Looking wider than Key Largo & the Upper Keys? See everything in The Florida Keys, or browse all Florida sailing schools, yacht clubs, and charter companies.
