The Southernmost Regatta- Key West Preview 2026
(Key West, FL)- The Southernmost Regatta, powered by Sailing Inc, will be sailing next week from January 19th to 23rd, 2026. Imagine being in gorgeous, sunny Key West, watching sunsets, chatting with friends we haven’t seen in months, and enjoying five days of excellent sailing in the aquamarine waters of the Florida Keys. Plus, there’s lots of wildlife down in the Keys, humans included! Don’t be surprised to see dolphins jumping and playing around your bows! And, watch out for those flying fish hitting your face! Without a doubt, sunfish sightings are not uncommon, and plenty of tarpon, barracuda, and sharks will be swimming just beneath your juicy toes dangling over the windward side!
The forecast (see above) for sailing on the picturesque blue waters off Key West should delight most sailors. “Breeze on” might be the theme for the week! Starting on Monday, NNW winds 15-25 kts, shifting slowly by Friday to ENE 13-20 kts, with strong breezes every day!
Participating will be a J/111 one-design fleet sailing their Midwinter Championship and an ORC Handicap Division. Both fleets will be enjoying what makes Key West a fabulous midwinter venue for sailing: the opportunity to race at a tropical venue, experience the eclectic island culture, and reconnect with friends at the infamous “Green Parrot” during the cold winter months.
J/111 Class
The half-dozen boats competing in the J/111 fleet are a mix of class veterans with plenty of silverware spilling off their trophy shelves and class newcomers that hope to learn a few tricks and compete with the top teams. It would not be surprising to see the three top teams duel for the podium all week long. Bill & Jackie Baxter’s FIREBALL is a menace on Long Island Sound, having won most events offshore. Sedgwick Ward’s BRAVO from Shelter Island has won its fair share, including the J/111 Midwinters. Plus, Rob Ruhlman’s SPACEMAN SPIFF team, famously from Cleveland, OH, has also been past Key West Midwinter Champions and two-time J/111 North American Champions! Handicapping this trio is about as sensible as handicapping the NFL Playoffs this weekend… hahaha. Any one of these teams can win the regatta; don’t be surprised if it’s a close three-way tie.
The J/111 “newbies” at Key West include Chip Merlin’s CHIP’S AHOY from St. Petersburg, FL, Roeland Polet’s FOREIGN EXCHANGE from Amherst, NY, and Tom Sutton’s LEADING EDGE from Houston, TX. While these teams are experiencing their first major J/111 one-design event in Key West, they are pretty competitive and have extensive offshore racing success on previous boats. Don’t be surprised to see some of them challenging the class veterans in races.
ORC Division
In this rather eclectic collection of a dozen offshore racing keelboats, Matt Schaedler’s J/122 BLITZKRIEG. How disparate is the fleet? It ranges from little wedges of cheese like the Cape 31s up to custom carbon Botin 44/45 “twins” at the top of the fleet! The BLITZKRIEG gang will have its work cut out for it against this cast of rogues. But over time, the J/122s have proven they love the often choppy medium breeze conditions that Key West is famous for… given the current weather forecast, they get plenty of that!
For more Southernmost Regatta Key West sailing information
https://www.yachtscoring.com/emenu/50230