For another year, the Whitebread around the Island is a joy

The 28th running of the Whitebread ‘round the whirl sailboat race took place this past Saturday. The Peconic Bay Sailing Association sponsors the race, which is a spoof on the original Whitbread ‘round the world race. In past years the Whitebread started in Cutchogue Harbor, circumnavigated Shelter Island and finished in Cutchogue Harbor, about 34 miles. For the past several years, including this year, the start line was Buoy N18, about halfway between Jessup Neck and Nassau Point, much closer to Shelter Island.

There are six divisions and boats are grouped according to their Performance Handicap Racing Fleet ratings. A boat may finish dead last, as I have done many times, and correct up to a winning position. The race is held in late September or early October when the wind can be out of control and the weather foul; this year it was perfect, dry and fairly warm with lots of wind. The Whitebread is the season’s last large regatta held in the East End of Long Island. This year there were 71 boats entered in the race.

I have been racing my C&C 24 since 1998, missing just several years, including last year. This year, one of my crew mates, Charlie Modica, suggested using his Alerian 33, Callaloo, with me as captain. Wow, what a difference, and I might add that my other long-time crew members, Linda Gibbs and Dave Olsen, were enthusiastic about the change of boats too. We went from being one of the slowest boats in the fleet to one of the faster ones, which brought some great news. Instead of being the first division to start and forcing us to leave my mooring in the dead of night, we could all sleep in a little longer and start and finish while it was still daylight. We did get to see a magnificent sunrise, however.

Friday afternoon Linda, my friend Dick Nystrom and I sailed Callaloo from Dering Harbor to West Neck Harbor in order to be closer to the start line on Saturday morning. Early Saturday morning, I met my crew of Linda, Dave, Charlie and Charlie’s brother, John Modica, who joined the crew for the first time, at the South Silver Beach Town Landing, where Tom McMahon motored us out to Callaloo. Having an extra crew member was definitely a plus in Saturday’s strong winds, as it gave us the extra weight needed on the rail to counter the wind. We all sail together with the Menantic Yacht Club and had as much fun on Saturday as we usually do racing Sunfish.

On our way out to Callaloo I reminded my crew of my three basic rules. One, we don’t go back for hats overboard. Two, we don’t go back for crew members overboard, except the captain. And three, we’re out to have fun but also to win. When Charlie and Dave lost their hats within the first half hour of racing, we followed Rule Number 1 and watched those hats drift away. Luckily, nobody fell overboard, so we didn’t need to test Rule Number 2. And as for Rule Number 3, we definitely had fun.

The race committee chose course Alpha, counterclockwise around Shelter Island. The wind was blowing from the west, which meant a downwind start. Callaloo has a small jib and performs best when sailing upwind, but we kept up with all of our competitors during this leg of the race. However, being the scratch boat meant keeping up wasn’t good enough in a long race. We not only had to cross the finish line first, but we had to give them all time. I’m not making excuses, but it was an awfully long downwind run.

Just after passing Jessup Neck we all heard a loud crunch and some rather loud language. Looking behind us, we saw three boats in our class bump up against each other. Other than that, it was clear sailing as far as I know. The spinnaker boats were the later divisions to start and it was a pretty sight to see as they approached from our stern. 

All members of my crew take turns at the helm. When Linda took over, just as we were approaching the buoy at Paradise Point, a couple of spinnaker boats were attempting to pass us on the inside. We gave them the needed space, when all of a sudden the nearest boat lost control of its spinnaker and we had to fall off sharply to keep from colliding. As we approached the buoy in Shelter Island Sound that needed to be left to port, it was rather crowded and Linda needed to do some maneuvering. Nothing like a little excitement to wake us up.

The only other time that we came close to anyone else was at the end, when we had to duck around one boat and do a couple of quick tacks in order to cross the finish line.

At the celebratory dinner that night, prepared by Master Griller Tom McMahon, we were just slightly disappointed when we read the results online and saw that we only came in third. However, nothing was going to ruin the glorious day we had on the water, and anyway, as I always say, there’s always next year.