An attempt at circumnavigation of Shelter Island

The 32nd running of the annual Whitebread Around the Whirl Sailboat Regatta took place this past Saturday in brutally tortuous conditions, even though being on the water is always better than being on land … I think.

The Whitebread is run in late September or early October when the weather can be unpredictable, really foul with howling winds, rain and cold requiring layers of clothing that never keep you warm and dry, or, on the other extreme, 80 degrees with very little wind requiring a shortened course. This past Saturday was the latter, in spades. It almost made the agony of defeat in years past preferable.

This regatta 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 some of the proceeds used to support youth sailing on the East End. Seventy-two boats registered for the race this year, but not everyone showed up for the start knowing what the wind conditions were going to be. The White-bread is a PHRF handicap-rated race with seven divisions. There is a spinnaker and a non-spinnaker fleet.

Each division has its own start time ranging from 9:20 to 10:20 a.m. The faster boats start later and usually catch up to the slower boats in short order.

The weather predictions for Saturday called for light and variable wind. During the skippers’ meeting in Greenport on Friday night, which I attended with John Colby and Dick Nystrom, the main discussion was the wind and/or, I should say, possible lack of wind and shortening of the course once the race started.

My crew makeup was slightly different this year. Linda Gibbs, a 20year crew member, missed the race for the third year in a row, and was replaced by Dick Nystrom, a newbie to the Whitebread. Charlie Modica, an 18-year crew member, couldn’t make it because of a whitecoat ceremony at St. George’s Medical School in Grenada, which he founded in 1976. Charlie’s brother, John Modica, another longtime crew member, arrived by boat from Connecticut in time for our 8 a.m. meet-up at Charlie’s house. John Colby joined the crew for the third year in a row.

For many years, I raced my C&C 24 in the Whitebread, but when Charlie offered Callaloo, his Alerion 33 a few years ago, the entire crew enthusiastically said, “Yes.” In addition to being a faster boat, sailing Callaloo, which is moored in Dering Harbor, meant leaving and returning in the daylight instead of the dark, even though the sunrise on the water is pretty spectacular. It was touch and go if Callaloo would be available, because she was undergoing a last-minute major repair. Many thanks to Schuyler Needham and his crew at Coecles Harbor Marina for working overtime to get her ready in time, because it was too late to enter my boat. When Schuyler called and said she was good to go, John Colby, Dick and I picked up Callaloo Friday morning from Coecles Harbor and sailed her to her mooring with a great sigh of relief. We would be racing after all. Thanks for the use of Callaloo, Charlie.

We arrived at the start at R 18 in Hog Neck Bay, west of Jessup’s Neck in plenty of time for our 10 a.m. start, and positioned ourselves for a start in winds so light it felt like we were just drifting over the start line. We were hoping to make it through Jessup’s Neck before the tide turned, otherwise we would be bucking an extremely strong current in near windless conditions, in other words, game over. To say it was slow going would be stretching the meaning of both “slow” and “going.”

We managed to pass George and Paul Zinger who were in a slower boat, but we were all just barely moving. Several faster boats passed us and got through Jessup’s Neck. We were optimistic and giving it our best … until we weren’t. The unthinkable occurred, we had to find the anchor, drop it and wait for what we knew wasn’t coming, stronger wind, at which point Dick deadpanned that being new to racing, he had never before realized that “anchoring” was part of racing.

It was around this time that I received a call from my wife, who asked if I had forgotten anything. Unfortunately, I had put the call on speaker and the crew heard the message that I had forgotten all the food, just as lunchtime was approaching. They glared at me, and words such as mutiny, walking the plank, and who should be sacrificed for lunch, were bandied about. And I thought they were my friends.

One by one, sailors started calling in to the Race Committee and retiring. We held tight for a while, but finally decided it was pointless to wait any longer for the inevitable, and we retired. On the way back to Dering Harbor, the wind did pick up and we started to second guess our decision to retire, until about 40 minutes later we heard over the radio that a number of other boats were joining the retirees.

As it turned out, Linda and Charlie just missed a nice day on the water. We all had a great time anyway, and as I say every year about this time – there’s always next year.

As it turned out, a lucky 13 boats did finish the race, none in my division. Congrats, to all.