The Columbus Day Regatta is Miami’s oldest regatta and one of the longest-running in Florida, sailed on Biscayne Bay over Columbus Day weekend, the long weekend around the second Monday of October.
A race and a raft-up
The regatta has two faces. The first is the racing: cruising and one-design classes sailing a course on the open bay south of Miami. Recent editions draw a few dozen boats, down from 1980s fleets that topped 700. The second is the anchor-out, the famous raft-up in the shallows near Elliott Key, where hundreds of boats tie together for one of the biggest floating parties in the country. For many people the party is the regatta; for the fleet up front it’s serious bay racing.
A little history
The event was started in 1954 by Timothy Sullivan, remembered as “the father of the Columbus Day Regatta.” It has run nearly every year since, standing down only twice: in 1992 after Hurricane Andrew, and in 2017 after Hurricane Irma. Over the decades it moved from the Coconut Grove Sailing Club, where it began, to the Coral Reef Yacht Club, with a committee of volunteers and a rotation of Biscayne Bay clubs and sponsors keeping it going.
How to take part
- To race, enter through the host club and its notice of race, which posts each summer. You’ll need a boat, a crew, and a valid rating for the handicap classes.
- To crew, ask around the Grove clubs and Miami sailing schools in September; boats are always looking for rail meat and trimmers.
- To anchor out, come by any seaworthy boat, but treat it seriously: it is a crowded, alcohol-heavy anchorage in thin water. Set a proper hook, watch your swing, and know that the shallows are unforgiving of a dragging anchor.
A word on the water
The raft-up sits over seagrass flats inside Biscayne National Park. Anchor on sand, not grass, keep your discharge closed, and pack out what you bring in. The party’s future depends on the bay staying healthy.
New to Biscayne Bay? Start with sailing in Miami and the Miami / Southeast region hub for the schools, clubs, and charters that make the bay one of the deepest sailing scenes in the country.
Last reviewed July 2026.