I Raced A Sailboat Around Lower Manhattan In Gusty Winds

Oracle’s Larry Ellison is known for his fierce competitiveness in the world of sailboat racing, especially the America’s Cup. Yet he also¬†once described the sport as “idyllic independence.” Now I understand what he meant — and why he loves it so much.

Over an intense weekend of learning and racing, I took the sailing challenge myself. Strong winds gusted as Charlotte Matthews, my instructor at Hudson River Community Sailing, and I navigated the sparkling waters of lower Manhattan.

The lessons culminated on Sunday in a competition against eight much more experienced crews. My colleague and producer, Justin Gmoser, crawled around the boat, documenting the whole adventure. In the end, he came away just as thrilled and exhausted as I did — and only lost one GoPro overboard in the process.

Produced by Justin Gmoser.

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