Florida sailing guides

The stuff that doesn't fit in a directory listing: how to cruise the Keys, what a charter company will ask before handing you the keys, when the wind is best, and the races worth planning a trip around.

Renting a Hobie cat in Florida

The fastest way onto the water in Florida is a beach cat off the sand: what a Hobie Wave, Getaway and Hobie 16 are like to sail, what the rental stands ask of you (usually nothing), and where the boats are, from Navarre Beach to Smathers Beach.
Adaptive sailing in Florida

Where a sailor with a disability gets on the water in Florida: the adaptive programs in Coconut Grove, St. Petersburg, Clearwater, Naples and Vero Beach, the boats and the docks and lifts they board from, the camps and courses for veterans, and how a first sail is arranged.
When to sail Florida

The best time to go sailing in Florida: the November-to-May prime season, summer sea breezes and thunderstorms, winter cold fronts, and how hurricane season shapes the calendar.
Youth sailing in Florida

How kids learn to sail in Florida: the community sailing centers and club junior programs, the boats they start in (the Optimist was invented in Clearwater), summer camp against the school-year program, race teams, high-school sailing, and how a parent picks one.
Sailing Central Florida's lakes

Where inland Florida sails: Lake Eustis and the Harris Chain, Lake Dora, Lake Monroe, Lake Weir and Orlando's lakes. The clubs, the winter regatta season, the public ramps, the scows and Flying Scots raced there, and what fresh water changes: no tide, and an afternoon storm.
Planning a Florida sailing vacation

How to plan a sailing vacation in Florida: crewed vs. bareboat vs. flotilla, where to go by season, and how to pick between the Keys, Biscayne Bay, and the Gulf coast.
Winter sailing in Florida

Florida's winter sailing season for snowbirds: what December to March is like in the Keys, Miami, the Gulf coast and the First Coast, cold fronts and north winds, air and water temperatures, where the regattas are, and how to sail a season without owning a boat.
Bareboat charter requirements in Florida

What a Florida sailboat rental asks before you take the boat: a sailing résumé, a checkout sail, or at two docks a certificate. What the 22 listed operators require as of October 2026, what ASA 101 to 104 cover, and your options if you are not there yet.
Catamaran sailing in Florida

Where to learn catamaran sailing in Florida and how it differs from a monohull: cruising cats vs. beach cats, the schools that teach ASA 114, which companies rent a cruising cat bareboat, and where the crewed and day-sail cats are.
Sailing the Florida Keys: a cruising itinerary

A leg-by-leg cruising itinerary for sailing the Florida Keys: Biscayne Bay to Key West and the Dry Tortugas, with anchorages, mooring fields, and how long to give it.
Yacht club reciprocity in Florida

How reciprocal privileges work at Florida's yacht clubs: what the Florida Council of Yacht Clubs and the Yachting Club of America's Register cover, what to bring (a club card, often a letter of introduction), the first-night dockage convention, the limits clubs set, and who states their terms.
The Columbus Day Regatta

What the Columbus Day Regatta is: Miami's oldest regatta and its famous Biscayne Bay raft-up, held over Columbus Day weekend since 1954. The racing, the party, and how to take part.
Living aboard a sailboat in Florida

What it's really like to live on a sailboat in Florida: mooring fields and liveaboard marinas, anchoring rules, hurricane-season planning, and where liveaboards actually keep their boats.
Hurricane season and your boat

How Florida boat owners get through hurricane season: what the written plan your marina wants actually covers, haul-out versus storm slip versus hurricane hole, the 72-hour checklist, and the insurance clauses to read before June.