For many, the denouement of the 2011 Caribbean 1500 rally took place in a crowded conference room in Hampton, Virginia, on Wednesday, November 9, two days after the rally’s original start date. The atmosphere in the room, as skippers gathered for what was expected to be the final weather briefing before the departure of the 61-boat fleet the following morning, was taut with expectation. To me it seemed everyone was quite anxious to get going. But when it was announced the start would be delayed—yet again—for another 27 hours, the crowd, to my surprise, burst into loud applause.

Clearly, there were many who were not anxious to confront the remains of Tropical Storm Sean, which had formed unexpectedly, then crouched for days right on the fleet’s rhumbline routes to the British Virgin Islands and the Bahamas.

For Larry and Cathy Clough, owners of Katahdin, the Cambria 44 I had signed aboard as crew, this last delay was only another lurch on a dramatic rollercoaster they’d been riding for weeks. They had rushed from yard to yard on Chesapeake Bay, scrambling to replace a failed packing gland on their rudder bearing, and for a while had sadly resigned themselves to missing the rally, which they’d spent years preparing for. Miraculously, the repair was completed just in time, and on the morning of the original start, just hours after I arrived to join the boat, Katahdin was hanging in a Travelift waiting

to be launched. When word came of the first postponement (just one day we were told), we were actually relieved, for now at least there would be time to test the repair before heading south to Tortola.

Several others were also happy to have more time, among them Ray Lillie, owner of Cool Change, a Fountaine Pajot Venezia 42 that was seized and impounded by a U.S. Marshal just prior to the original start. Beyond muttering something about a dispute with a local boatyard, Lillie wasn’t willing to discuss the matter with me. He did manage, however, to regain control of his boat on Wednesday, just after the final delay was announced, and immediately donned a headlamp and dove into a deck locker to complete his preparations.

There were, in all, three postponements—with the start shifting from Monday to Tuesday to Thursday and finally to Friday of that week as Sean slowly evolved. To their credit, the rally organizers fully comprehended the consequences of the last delay and were prepared. For as soon as the applause died away in that conference room, there was a rush to the front desk as skippers scrambled to replace crew who just couldn’t wait that long. Among these, sadly, was my skipper, Larry, as I was one of the schedule-burdened unfortunates who could not risk getting caught in the “crush zone” between the finish in Tortola and the Thanksgiving holiday.

Another skipper with scheduling problems was Bob Woods, owner of Lexington, a Morris 46. Like Larry and Cathy Clough, Bob was a bluewater virgin who’d spent years plotting his participation in the rally. But unlike Larry and Cathy, his crew—five fellow members from his local sailing club in Kentucky—were co-conspirators from the get-go. They had helped prep the boat and donated much gear, and he wasn’t about to leave any of them behind. To accommodate them, Bob told me after the Wednesday briefing, he figured he’d have to sail with the smaller Bahamas fleet (a group of nine boats headed to Green Turtle Cay in the Abacos instead of Tortola) so as to shorten

his passage time.

“How do you feel about that?” I asked him.

And he shrugged: “I want to do this with these people. I don’t care so much where we go.”

A Slow Slog South

The several delays before the start of the rally had two immediate consequences: first, there was that much more time for rally-goers to hang out and bathe in pre-start camaraderie; second, soon after the official start on Friday, November 11, conditions turned light as a big high-pressure cell moved in and most boats had to run their engines hard to make progress south.

One small group of three boats, Lexington among them, did decide to strike out one day early for Tortola, and thus were considerably farther south when the wind died. Bob Woods explained to me later that his decision to leave early rather than sail to the Bahamas was made in an instant when he saw Nyctea, a Beneteau Oceanis 46, and 1700 Somewhere, a MacGregor 65, setting out on their own on Thursday.

“Forty-five minutes later we were slipping our dock lines and heading out to the start line,” he wrote. “We radioed the rally control office to inform them of our decision.”

Meanwhile, several other boats in the main body of the fleet soon ran short of fuel and diverted to Bermuda for more. Other than the boats that started early, the only ones to reach the tradewinds in good time were the larger, faster vessels, like Fat Cat, a custom Morelli & Melvin 80 catamaran that left Hampton a day late due to equipment problems. The big cat eventually overhauled the next fastest boat in the fleet, Black Bird, a carbon-fiber Tripp 78 monohull, and took line honors in Tortola after spending little more than five days at sea.

Most other boats, meanwhile, took 10 days or more to reach Tortola, and some, including rally founder Steve Black aboard his Pacer 42, Madrugada, were disappointed to find the finish line was already closed when they got there. Most others didn’t really care. Rally staff from the World Cruising Club kept the parties rolling for late-comers, and two of the last boats (one of them sailing under an emergency tiller) serendipi- tously appeared to great acclaim just as the final prize-giving was about to get underway.

The boat I was most interested in, of course, was Katahdin. I was relieved that Larry and Cathy were able to find crew to replace me, but I was very sorry I was not aboard. Their trip south, as with most of the others, started with lots of motoring (they burned 70 of 90 gallons of diesel aboard), and ended with a glorious broad reach in 25-knot tradewinds. There were some minor gear failures, but these were easily handled. Inevitably, too, perhaps, their arrival in the islands seemed anti-climactic.

“Last but not least, the rudder fix performed flawlessly,” wrote Larry in an e-mail. “So much agony. At one point I had given up on the 1500, but we kept on slogging. It is hard to believe we are finally here after 3 years of planning and reorganizing our lives for this trip. At dinner last night at a local bar, there was a definite sense that after focusing on this goal for so long we felt at loose ends in finally passing the finish line.”

All in all, I reckon, this really isn’t such a bad way to start a winter’s sailing season in the Caribbean.

Photos by Sara Proctor, Charles J. Doane