We were maybe half a mile from the leeward mark, surging along relentlessly aboard the X-65 Karuba V, when the rig came down to the accompaniment of a collective gasp from the crew. Thankfully, it wasn’t our rig—but we did feel sorry for the guys on Highland Fling XII, Irvine Laidlaw’s spanking new Reichel-Pugh IRC 52. Their Code 0 had caught on a spreader and that was that—a timely reminder that hundreds of thousands of dollars and meticulous preparation are no match for a moment’s ill-judged crew work.

Highland Fling’s International Rolex Regatta was over on race one of day one, but for Karuba V’s crew, the fun was just beginning. Owned by a personable Croatian couple, chartered for the event by a group of affable Russians who normally race in the Med, with a crew comprised largely of whomever regatta co-chair John Sweeney could round up on the dock each morning, the comfortably appointed cruiser-racer was perhaps not representative of a typical Caribbean IRC campaign. She was, however, entirely representative of the international flavor of this long-lived event, which attracts boats and sailors from all over the world. 

The Rolex battle flag snapping from the crosstrees of the St. Thomas Yacht Club’s flagmast (it’s more than just a flagpole) marks the spot where the Swiss watch company started its long association with international sailing. Even today the clubhouse, mere steps from the beach in Cowpet Bay, is a model of Caribbean informality; I can only speculate as to what it must have been like in 1974 when the inaugural Rolex International Regatta took place. 

Certainly the atmosphere, as welcoming and relaxed as anywhere I’ve been, can’t have changed. Having already sampled the delights of Antigua Sailing Week, the Heineken Regatta in St. Maarten and the BVI Spring Regatta, I was skeptical of the RIR’s claim to be the “crown jewel” of Caribbean sailing. Now I may be a convert. I can attest there’s no better venue for a party than this; the fact that most of the boats moor in Christmas Cove each night, far away from Charlotte Amalie, means that most crews naturally head for the club for dinner and a few beers. Such a captive audience of thirsty sailors can only mean one thing…

Also, the racing conditions are excellent, with courses stretching along the beautiful coastlines of St. Thomas and St. John and around the islets of Pillsbury Sound. The first race of the weekend finished in Charlotte Amalie Harbor, which must have made for a great spectacle from shoreside. 

Breeze was in good supply, as is usual in late March. On Karuba V, the pickup crew managed to bend the big masthead kite to its collective will, despite the inevitable foul-ups as competing instructions were conveyed in three languages and the sailing master ran himself ragged coordinating our efforts, gaining in the process one of the most impressive rope burns I’ve ever seen. It was a reminder, if I needed it, of the immense loads on a boat this size in such conditions. Placed in charge of the spinnaker pole topping lift and foreguy, all I had to do was concentrate on not braining the bowman during our rather exciting dip-pole gybes.

Highland Fling’s dismasting was, thankfully, the major drama of the weekend, excepting the photo finishes in three of the six classes. Peter Cunningham’s TP52 PowerPlay (IRC-1), Andre Scarabelli’s Melges 24 Budget Marine/GILL (CSA-1) Jonathan Lipuscek’s J/105 Dark Star (CSA-2), Antonio Sanperre’s J/36 Cayennita Grande (CSA-non spinnaker), Fraito Lugo’s Orion (IC-24) and Jorge Ramos’s Hobie 16 Universal (Beach Cats) won the Rolex watches this time around. A bunch of disparate boats for sure, but you can bank on one thing: most of them will be back next year. And so, hopefully, will I.