Updated on October 2, 2003

The "Race" Around Islesboro

Although I have sailed more than a few time, and have even taken formal sailing lessons on a number of occasions, I cannot claim to be a "sailor." Sailing, like many sports, takes time, effort, and practice, practice, practice to master. Although I have made the effort to learn to sail, I've fallen far short on the "time" and "practice" elements to even begin to think of myself as a sailor.

Sailing does, of course, require a sailboat. I did, in fact, own a sailboat at one time. For a day. A long story that doesn't need to be told here. Since then, I have made the rather rational decision that it is better to know someone who owns a boat rather than actually owning the boat yourself. A lot cheaper, for one thing. And although this strategy won't allow me to truly become a sailor, it does afford me the occasional pleasure of spending a splendid summer day plying the waters of Penobscot Bay in a vessel powered solely by the wind.

Such was the scenario earlier this month when I was asked to crew on a boat entered into the annual "Race Around Islesboro" - the season finale of the Northport Yacht Club racing season. Islesboro is a long, thin island stretching some 13 miles from end-to-end, sitting directly east of Bayside. About 600 people call the island home year round, and many more have "summer" homes there, including the likes of John Travolta and Kirstie Alley. But on this day, we weren't interested in trying to spot celebrities, we were focused strictly on circumventing the island as fast as possible. Well, okay, that is a bit of an exaggeration. Our primary focus was on having fun, which was fortunate because if we were focussed on winning, we would have had a miserable day.

There would be five of us aboard the "Skedaddle" that day - and only one, Jon (the skipper), could be called anything close to a "seasoned" sailor. But we didn't let that fact dampen our hopes for glory. And, indeed, we came out fighting. It was recorded in posterity in a color photo that draped across the front page of the local newspaper that the Skedaddle was solidly in the lead as the racers crossed the start/finish line. Of course, at this point in the race, it would more accurately be referred to simply as the "starting" line, but we're not ones to quibble about semantics - we'll take the glory no matter how fleeting.

The race was open to sailboats of all sizes, with the boats being handicapped to account for the differences in size and capabilities of the various crafts. Prior to the start of the race, one had to declare whether his/her boat would participate in the "racing" class or the "non-racing" class. The later category was a misnomer in that every boat was actually racing - the only difference between the two classes was that the boats in the "racing" class were allowed to use spinnakers (the colorful, puffy sails that are able to catch the lightest of breezes). The Skedaddle was officially in the "non-racing" class, so we wouldn't be dealing with a spinnaker.

Although it was a gorgeous day to be on the water - sunny and warm - it was not an ideal day for sailing. This was due to the fact that there was a noticeable lack of wind. Fortunately, there was some wind, so we could, in fact, make progress. But the breeze was light, which promised to make the going slow. We were, of course, prepared for this eventuality. The race started at 10 a.m. The first beer was opened at 10:30 a.m.

Due to the fact that they had more potential sail power, the boats in the "racing" class, spinnakers hoisted, started 10 minutes after those of us in the non-racing class. This was fortunate in that it gave us some incredible photo opportunities - there are few sights quite as beautiful as a fleet of boats flying colorful spinnakers while bobbing on a cobalt blue sea.

Not so gradually, we began to lose our position as lead boat. Soon, most of the "non-racing" fleet had passed us, and even some of the racing fleet, having started 10 minutes after us, were quickly approaching. I cannot stress strongly enough that this was not due to sailor ineptitude. We simply had a slow boat. That's my story and I'm sticking to it!

About two-thirds of the way down the southern reach, the vast majority of the boats in the race were becoming specks on the horizon out in front of us. We had broken out the junk food by now and were blissfully indulging in a cornucopia of empty calories, taking comfort in the fact that we were far from the watchful eyes of our wives who would no doubt reprimand us for our plunge into the nutritional abyss. The winds remained at bay, and by now the younger among the crew were outwardly expressing their frustration at our lack of progress and wondering what they had done in life the warranted such torture. The older among the crew simply popped open more beers.

As we approached the southern end of Islesboro, we began to hear the radio messages of the boats who were rounding the island and heading north. The calls were expected, but were depressing nonetheless in that they only served to reinforce how far behind we were. Eventually we, too, neared the point where we would be able to call in and let the race organizers know we were coming around. By this time, there was only one other boat in sight, and we took turns passing each other. As we made our way through a harbor, we suddenly (well, as "sudden" as things can get when you're moving relatively slowly) came to an abrupt halt. The unthinkable happened. We had ran aground!

How could this have happened, we wondered. The boat had a depth meter. The captain was sure that we would be fine in anything deeper than six feet. The captain was wrong. We were stuck.

At times like this, the tide can work for you or it can work against you. In these parts, the difference between high and low tide averages 8-10 feet, so depths can change quite rapidly, up or down, depending on whether the tide was going in or out. Unfortunately for us, the tide was going out. We would have to work hard and work quickly, or we would be stuck until the tide came in.

We could not, of course, start the motor since that would disqualify us. Instead, we had to make use of what little wind there was and try to maneuver the sails to back us out of our dilemma. It took a good 10 minutes or so of effort, but we were finally able to free ourselves.

As luck would have it, the other boat with which we were jockeying for position (the position being second-last place, rather than last place) also ran aground. They, too, were able to free themselves, but we managed to sail past them as we rounded the island and after that they just kept falling farther and farther behind.

The rest of the sail was uneventful. When we rounded the north end of the island and headed west towards the finish line, we finally encountered some decent wind. This allowed us to pull further ahead of the last place boat, and to get surprising close to some of the boats that had seemed so far ahead of us. As we approached the shore, however, we realized why we had been able to close the gap. About one-third of a mile from shore, we hit the doldrums, coming to a near stand-still. The going was considerably slower from here on in, although we did manage to eke past another boat before the finish. The official cut-off time was 7 p.m., and we managed to beat that by a good 45 minutes. In all, we took a little over 8 hours to make the journey.

And what became of the boat we passed at the south end of Islesboro? They ended up coming in about 40 minutes after we did. The official results, however, would show that they finished ahead of us due to the fact that they had a smaller boat and a higher handicap. Counting the one boat that did not finish, we officially came in third from last. But, most importantly, through it all we never ran out of beer or junk food.