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.
The 2026 edition, the 71st, was sailed on Saturday October 10, 2026, hosted by Coconut Grove Sailing Club with Columbus Day Regatta, Inc. It ran as a pursuit race, one race for all classes from the 11:30 warning signal near the Donovan’s mark at the end of the Dinner Key Channel, and the provisional results on Regatta Network score 41 boats in five classes: Relentless III won the first assigned-rating class and Dona Pituca the second, Colombian Princess the one-design class, Michael Pierce’s boat the Shake-A-Leg Freedom 20 fleet, and Third Tri 2 sailed as the lone multihull. The awards party was at Shake-A-Leg Miami. The 2027 notice of race goes on the regatta’s event page when it posts; in 2026 it appeared on Regatta Network on September 4, with entry closing three days before the race.
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, 41 in 2026, 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. The 2026 edition was back at Coconut Grove, run by the club with Columbus Day Regatta, Inc.
How to take part
- To race, enter through the notice of race, which usually posts over the summer (September 4 in 2026, with a $75 entry, waived for the Freedom 20s, closing the Wednesday before the race). The 2026 NOR took five classes: an assigned-rating class open to any boat 16 feet or longer with present or past racing ability, a one-design class for any fleet that musters five entries, multihulls 24 feet and up on MASF ratings, beach cats 16 feet and up, and Shake-A-Leg Miami’s Freedom 20s, sailed by disabled and able-bodied competitors together (the adaptive sailing guide covers the fleet). Boats without a rating send a photo and the manufacturer’s specifications with the entry.
- 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 October 2026.