42nd Annual Schooner Wharf Bar Wreckers Race Series - January

Schooner Wharf Bar Wreckers Race Series – January 2027

A true Key West sailing tradition returns as the 42nd Annual Wreckers Race Series launches from the Historic Seaport at Schooner Wharf Bar. Inspired by the island’s storied wrecking history, this spirited race invites captains, crews, and spectators to celebrate classic seamanship and friendly competition on the open water.

Festivities begin Saturday evening with the Captain’s Meeting, where strategies are shared and rivalries begin to stir dockside. Sunday’s race sends a colorful fleet of schooners, sloops, and local vessels across the Key West harbor in pursuit of victory—and bragging rights.

From the docks, the energy builds with live music, cold drinks, and front-row views of sails cutting across the horizon. Whether racing or watching, this is one of the most authentic ways to experience Key West’s maritime soul.

Date based on annual scheduling pattern—subject to official confirmation.

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