In mid-August, the island of Nantucket becomes the beehive around which competitors and spectators of Nantucket Race Week and its finale, The Opera House Cup Regatta, buzz. Boats of all sizes, from the Alerion fleet to larger classic yachts find their regular spots in the mooring field or the docks and a certain reunion ensues. Most crews come in for the full Race Week, some actually racing, all drinking, until the Cup rolls around. When I ferried in on Thursday, the 12 Meters flanked our ship, sails down, headed in for the day.

Since the island was as packed as one might imagine, I took refuge in an invitation for an evening aboard Bolero. In the cabin of the gorgeous German Frers 105 foot maxi racer, fresh caprese salad from Bartlett’s Farm was served to a few of us sailors in the most civilized of fashions. Wine and key lime pie followed in the cockpit while tourists strolled by licking ice cream cones—not a bad start to the weekend. If they knew we were telling bad humor holding tank stories, they might not have been so impressed. “Is there a race this weekend?” one passerby asked.

A race indeed.

Sponsored by Officine Panerai, the Opera House Cup, in its 40th year, is the second stop on the North American Circuit of the Panerai Classic Yachts Challenge. The Cup was the first all-wooden, single-hulled classic boat regatta on the East Coast, and while specifications have eased to allow non-wooden boats in the “Spirit of Tradition” class, the regatta carries on the appreciation of timeless vessels.

For the main event, I was lucky enough to be invited aboard Heroina, a 74-foot wooden sloop that is another German Frers design. Most sailors know Frers for his work with Nautor’s Swan and Hallberg-Rassy. But he has also designed such classic boats as Rebecca, a 138-foot yacht, and the 203-foot ketch Loa. But Heroina was not built for a company or a customer—it was built for Frers’s own use, though after 15 years of under-use, she was sold in 2009. A year ago, she was sold again to an owner who brushed off the cobwebs and finally plans to take her out as much as she deserves. Starting now, with possibly her first-ever regatta.

For the full experience and to see our downwind finish, check out Tucker Thompson’s video with commentary. Heroina can be seen at 10:23.

The first thing I noticed as I was shuttling out to Heroina, was that the mooring field was something like a pinball machine, with the mooring balls too close to accommodate the waterline of their hangers-on. As the wind shifted, boats swung dangerously close, their crews on watch.

Despite the fanfare (Brant Point looked on the verge of sinking due to the number of spectators waving us off), the 2012 Opera House Cup Regatta was without a great deal of excitement. The wind was not exactly howling and many of the smaller boats, the Alerions in particular, did not finish the 20-mile course. As I was on a larger yacht, rewarded with the distinction of “First to Finish” in fact, I can’t complain about the length of the race. But as my entire experience in yacht racing up until now has taken place in a small one-design class, I found it, dare I say a tad boring to be so far ahead of the rest of the fleet that our view switched from a direct view of horizon to island on each tack.

The excitement, for me anyway, came from being on such a gorgeous piece of woodwork. On board, the yacht looks larger than its 74 feet, and it moves as though powered from within. Heroina’s new owner was of the “present” variety, though preferred to stay anonymous. He was hiked out with the rest of us, jogging from rail to rail. The captain, Marius Swart did the talking…he and Captain America, that is. That’s right—our mascot was a toy Captain America that peeked out of the owner’s pocket and pronounced motivating speeches to lighten the mood.

Finding a spot among the international crew as Heroina plowed ahead despite the lack of wind, I enjoyed a nap on the teak deck during the last downwind leg. With no one ahead of us, and John Kerry’s W boat, Wild Horses, sneaking up from behind, the crew poled out the main in a last attempt to increase speed, but there was still enough distance left to give our competition time to catch up. In the end, with handicaps tallied, we were 15th out of 31 boats. Wild Horses indeed overtook us and took 12.

Of course, what everyone on Nantucket was really interested in were the parties over Nantucket Race Week, especially the Opera House Cup awards party on Jetties beach. The evening began with a spectacular sunset and a good time was had by all, regardless of whether or not they walked away with a new Panerai watch. Though, for the record, that honor went to the 8 meter sloop Quest.

Top photo by Cory Silken courtesy of Panerai; all other photos by Lindsey Silken