Shelter Island sailors in annual Whitebread Race

The 31st annual Whitebread Regatta was run this past Saturday in near perfect conditions. 

The Whitebread is a spoof on the original Whitbread around-the-world-race. Instead of the world, this race, hosted by the Peconic Bay Sailing Association, circumnavigates Shelter Island, with the proceeds used to support youth sailing on the East End. It is a PHRF handicap-rated race with six divisions; the slower divisions are divided into two classes. Each division has its own start time ranging from 8:30 to 9:20 a.m. The faster boats start later and usually catch up to the slower boats in short order. 

This year, the course started and finished at buoy R18 in Hog Neck Bay instead of in Cutchogue Harbor, where it has started and finished in the past. The shortened course allowed my crew and me a little extra sleep time, and allowed us to leave and return in the daylight, although watching the sunrise from a boat is always a pleasant experience. 

John Colby and I attended the skippers’ meeting Friday night in Greenport and ran into James Eklund on the ferry on the way home. We were all thrilled that the race was going to start and finish at R18.  

The Whitebread is held in late September or early October and is the last large regatta of the summer on the East End. Having entered this race about 25 times, I know from firsthand experience that the weather can be perfect, like this past Saturday, or really foul with howling winds, rain and cold. Registering well in advance of race day, one never knows what to expect. I’ve encountered days with little to no wind and 80 degrees. Other days the wind is howling with rain requiring layers of clothing that never keep you warm and dry. 

One year my crew mutinied before we even reached the start line because the weather was so bad. Those crew members were all prosecutors and defense lawyers, and I’m not, so what chance did I have when they stared me down? In all fairness, it was so rough at Jessup’s Neck that day that water was cascading over the transom, stalling the auxiliary outboard on my C&C 24 and filling the cockpit with water, but still …

For the last four years we’ve used Charlie Modica’s Alerion 33, Callaloo, instead of my C&C 24. When Charlie first broached the idea it only took a second for the crew to agree to the larger, faster and more comfortable boat. This year my crew consisted of Charlie, John Modica, and John Colby, all friends from the Menantic Yacht Club. Linda Gibbs missed the race again this year. We all felt the presence of the late Dave Olsen cheering us on from up above, and held this race in Dave’s memory, including a post-race toast in his honor. 

Dave, an excellent sailor and all-around great guy, was my crew member for 18 years, and he is missed by all who knew him.  

Leaving Charlie’s dock in the light with just a drizzle forecast and 10-to-15  knots of breeze, we were all in high spirits and gunning for that elusive win and a trophy. Callaloo was the scratch boat in our class again this year, a position I really don’t prefer. It means that we have to beat every boat in our class across the finish line and give them all time.

About 15 sailors out of the 69 boats registered were from Shelter Island this year, including Paul Zinger, James Eklund, John Sommi, Jerry Zisfein, Issac Halpern, Pat Mundus, Steve Lubitz, Jeffrey Pribor, Stephen Guyer, Andrew and Sedgwick Ward, Harry DiOrio, Peter Chinetti, Greg Cukor, David Kriegel and Peter Brechter. Not a bad turnout from Shelter Island.

We didn’t have an especially good start, and were behind several boats in our fleet, including Foxfire captained by Peter Brechter. Considering we were the scratch boat and had to give every boat in our fleet time, it was an ominous start and we knew Foxfire was the boat we had to beat. We kept getting closer to Foxfire as the day progressed and thought that we had passed her in the rough choppy waters of Gardiners Bay, where we lost sight of her. In fact, we lost sight of most of the other boats in our fleet, which was designated by black flags, and thought that we were in pretty good position and moving fast. 

As we were passing through South Ferry, the ferry captain slowed down in order to let us pass without having to jibe in order to miss him. Ferries have the right of way, and I thank you. Approaching the finish line we couldn’t see any black flags until we did, and we knew first place was off the table when Foxfire passed us on her way home before we even reached the finish line. 

There was still hope of coming in second or third, right up until the results were posted and we ended up in fourth after 4.1 hours of racing.

My crew and I are already anticipating next year. Congratulations to all the winners and to all who entered and had a great day of sailing.