Southernmost Regatta
When: January 19 - January 23, 2026
Where: Key West, FL 33040
Experience the Excitement of The Southernmost Regatta
January 19–23 | Key West, Florida
Visit: southernmostregatta.com
The Southernmost Regatta is a premier sailing event bringing together elite sailing teams from around the globe to compete in the stunning azure waters off Key West, Florida. Over five consecutive days of exhilarating races, vibrant sails, and unmatched sportsmanship, this regatta has become a highlight of the winter sailing season. Open to One Design and ORC Racing/Cruising Keelboats, the competition promises high-quality racing and unforgettable moments for participants and spectators alike. Visitors can enjoy breathtaking views of the action from various waterfront vantage points.
Powered by Sailing Inc. – A Celebration of Racing and Community
The Southernmost Regatta is committed to delivering an exceptional and sustainable sailing experience. The event not only highlights competitive racing but also fosters camaraderie by bringing together sailors, industry partners, and enthusiasts in a welcoming and vibrant environment.
What to Expect
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Five Days of Competitive Racing
Immerse yourself in world-class racing on Key West's iconic blue waters. The event features two daily races across two courses: a One Design Course and an ORC Course. Additionally, ORC cruisers can participate in a unique distance race each day. -
Back to the Basics
Rediscover the essence of what made Key West racing legendary—thrilling competition, the charm of island culture, and the warmth of reconnecting with the sailing community during the chilly winter months.
A Legacy of Excellence
Racing in Key West has a storied 30-year history, creating a tradition that has become more than an event—it’s a way of life. Rob Ruhlman, a passionate advocate for the regatta, reflects:
"Racing in Key West had an epic 30-year run... The opportunity to reignite that flame, albeit on a much smaller scale, is worth pursuing in the hope that when properly fanned and fed the fire will once again burn brightly."
Don’t miss your chance to be part of this vibrant celebration of sailing. Whether you’re a competitor or a spectator, The Southernmost Regatta offers a perfect blend of adventure, community, and the unmatched beauty of Key West.
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