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.

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.
Bareboat charter requirements in Florida

What you actually need to bareboat charter a sailboat in Florida and the Keys: the ASA 101/103/104 path, the sailing resume charter companies ask for, and your options if you're not there yet.
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.
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.
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.
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.
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 on multihulls, and how to charter one in the Keys.
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.