A perfect day for Whitebread

The 33nd running of the annual Whitebread Around the Whirl Sailboat Regatta took place this Saturday, Oct. 3, in the waters surrounding Shelter Island and vicinity. The Whitebread’s name is a spoof on the original Whitbread around-the-world-race.

Sixty boats registered for the race this year, including 13 from Shelter Island. Instead of going around the world, this race, hosted by the Peconic Bay Sailing Association, circumnavigates Shelter Island, with some of the proceeds used to support youth sailing on the East End. The Whitebread is a PHRF handicap-rated race with seven divisions. There is a spinnaker and a non-spinnaker fleet, and each division has its own start time ranging from 9:20 to 10:20 AM. The faster boats start later and usually catch up to the slower boats in short order. This year we were nearing the finish when the last of the spinnaker boats passed us.

The Whitebread is run in late September or early October when the weather can be unpredictable, The weather was perfect on Saturday, mild, no rain and windy. 

For the past seven years we’ve been using Charlie Modica’s Alerion 33, Callaloo, instead of my C&C 24. It’s faster and has a later start time. Instead of meeting up at 5:30 a.m. we met up at 8a.m. My crew might not like to hear this, but I miss the early morning sunrise on the water while sailing to the start. But I’ll take the faster boat and later start anytime. My crew this year consisted of Linda Gibbs after a three year absence, John Colby, Charlie Modica, Sr., and Charlie’s friend Joel Feldman. 

The wind was predicted to be strong in the morning and then die down. During the Skippers’ meeting Friday night the PRO talked about shortening the course if necessary, and it was eventually shortened to R20 off Nassau Point even though the wind was good all day. In fact, we weren’t sure we would be able to carry the full sail at first but we only had to work the main sheet in the puffs to keep from rounding up during the upwind sail. 

Unlike last year, when most of the fleet anchored short of Jessup’s Neck because of lack of wind and a strong current pushing us backwards, this year we not only had a strong breeze but a favorable current. From the start at R18 in Hog Neck Bay we needed to tack twice before reaching paradise point. A reach brought us to Jennings Point in short order. The entire fleet was moving quickly and hoping to make it to Gardiners Bay before the wind slowed down. From Jennings Point we did multiple tacks to stay in the strongest part of the current until we rounded N6 in Orient Harbor. On the Alerion with its self-tacking jib we didn’t lose much time during the tacks. 

The spinnaker and non-spinnaker divisions sailed clockwise around Shelter Island, but on two separate courses. The spinnaker division course included leaving both G7 in Hay Beach and MOA in Gardiners Bay to starboard. My non-spinnaker division had to leave N6 in Orient Harbor to starboard and then head to the point off Ram Island. Fortunately, the fleet was spaced out enough that we only had to duck one boat heading down to Ram Island while that boat was heading to MOA.

While sailing past Bug Lighthouse on the way to Big Ram Linda and I were glad we were wearing our foul weather gear because it was pretty rough and we were taking water over the bow. The other crew members got a bit wet but it didn’t bother them. 

It was pretty much a fast reach from N6 to Big Ram where we started a long downwind sail eventually to the finish. Looking behind us we saw the spinnakers starting to fly, a beautiful sight. 

Our start time was 9:50 am, and as we approached Coecles Harbor it was just past noon. We were making good time and all agreed it was lunch time. Last year I forgot to bring the food and had to quell a small mutiny, so I was especially diligent about remembering it this year. Next rounding was Mashomack and a short reach to South Ferry, then downwind to the finish. 

From the very start we were trying to catch five boats from our division, knowing that we had to pass at least one of them in order to place in the top three. We saw four of those boats cross the finish line in front of us in what looked like a photo finish but hoped that we would correct up. When we saw that George Zinger was one of those boats our hopes faded because he was the highest numbered PHRF boat in our class, but it wasn’t until the final results were posted that we realized once again that … there is always next year.

As always, we held a dinner party for the sailors after racing. This year I invited another Shelter Islander, Jerry Zisfein the skipper of Hound, and his crew of Jodi Sisley and Dick Nystrom. Unfortunately, Jerry had motor problems after finishing the race, and even though it took him four hours to sail home arriving in the dark, it didn’t dampen his or any of our spirits during the loud and boisterous evening. 

Congratulations to all the sailors who participated in a fun day on the water.