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« Back Post Date: Tuesday, October 02, 2018, 1:00 PM
A “Relaxing” Month off From School
Junior member Jacob Kawolski ditched the first month of senior year to race and train at Oakcliff Sailing Center on Long Island. He’s back now and fully amped on big-boat and offshore sailing. He’s also looking for a ride…

It took one year of scheming and machinations to convince my parents to allow me the pleasure to skip the first month of my senior year of high school. You may ask, “What lunatic would skip the first month of one of their most important years in school?” I would! All for the sake of racing offshore at Oakcliff Sailing in Oyster Bay, New York.

I was drawn to the program for a number of reasons. First, they recently acquired a JV66 calledNumberswhich is kind of like a 66-foot-long 49er made entirely of carbon fiber. I was able to sail this boat along with many other high-performance offshore racing boats, such as a Kerr 50 and Farr 40. And during my downtime, I had unlimited access to a fleet of foiling NACRA 17s, Waszps and 49ers. Needless to say, I’d found heaven on earth.

Even better, the fun at Oakcliff wasn’t limited to sailing. I learned countless tips and tricks for boat rigging and maintenance. I can now confidently disassemble and reassemble any winch or splice any line. We were also given multiple days to learn about rigging and engine maintenance, frequently experimenting with Oakcliff’s boats. We learned about composites and boat paint (may that Laser we “painted” rest in peace).

I had the time of my life.

I and the other youth sailors raced in two regattas: Ida Lewis and the Vineyard Race. During my maiden offshore race at Ida Lewis, I was christened by a torrential downpour and thunderstorm. However, I got to have the last laugh, as all the heckling I’d been taking for bringing my drysuit suspiciously stopped. We placed rather well in our little Oakcliff flotilla. We were racing a Farr 40 and were lucky enough to beat another Farr 40 and a Class 40.

We were much more successful at our second regatta, the Vineyard Race. The race conditions were rather brutal for the first half. It was 140 nautical miles almost directly upwind, but the pain was offset by our effective sailing. We had the privilege of having Volvo Ocean Racer Dawn Riley as our skipper, and she did a fantastic job. We rounded the mark in second, only behind one IMX 45 and ahead of two XP 44s and the infamous heavily modified J/120 Desperado. We held our position for the downwind leg and came over the line in second. However, our unfortunate IRC rating moved us to 4th on corrected time. But I loved every second of the Vineyard Race, and wouldn’t hesitate to race it again and claim our rightful 2nd!

Overall my time at Oakcliff was wonderful. I left after a month heavy-hearted and sad to leave the East Coast and their supply of offshore regattas. Now that I’m back in California, I’m beyond excited to take what I’ve learned and expand it at St. Francis. I’d love to hop on any boat, big or small. If anyone is looking for a crew for any race—match racing or offshore or buoy racing—I’d be happy to come sailing and learn all I can. You can email me at  

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