The Caribbean Caravan

Indeed, a strong emphasis on safety permeates the Caribbean 1500, even though no safety checklist, after all, can guarantee a safe passage. Still, our safety inspector, Jeff Chabot, who's sailed several 1500s in his own boat, not only works through the required items on the checklist but walks my wife, Harriet, and me through the nitty-gritty of what to do in the event of a crew-overboard, a holing, a dismasting, or a steering failure on our Dolphin 460, Hands Across the Sea. After we arrived in Tortola we found there's a kind of safety postmortem, too, embodied in the form of Davis Murray, Steve Black's ocean-sailing compadre and Caribbean 1500 go-to guy. (For more on Murray, see "The Master of Deviation," September 2008.) Any boat arriving with a gear failure soon finds Murray up the mast or down in the engine room determining the cause of the breakdown and assessing how the crew handled it. Why and how did the part break? Did you have the right spares/repair parts/tools/know-how to get it up and running? The information Murray uncovers is incorporated into the next year's safety requirements and inspection.

Another feature that attracts cruisers, particularly those new to passagemaking, is the event's 200-strong volunteer-crew service. Black notes that about a third of the 2008 entries haven't made a passage of longer than two nights; most of the rest of the fleet are 1500 veterans. Before each event, Black plays matchmaker, getting 1500 veterans onto boats with little or no offshore experience and matching volunteer crew with specific boat types and boats. For Kent and Carol Bradford and their Bristol 45.5, Destiny, for example, Black lined up 1500 vets Galen Hake and Mike Eslinger-both are Bristol 45.5 owners, and both have sailed their own boats offshore. Ultimately, nearly every boat in the rally carries a volunteer sailor.

Finally, the attraction for many of this and other rallies is camaraderie-and, I suspect, curiosity. Wanting to make new friends who are going where you're going is a natural, and that leads to dockside kibitzing about approaches to everything from passagemaking to rum-drink recipes to the cruising life. And as everyone eyes everyone else's boat and gear, there's plenty to be learned and applied to your own boat. The gathered Caribbean 1500 fleet is a kind of showcase of well-equipped modern cruising boats averaging 48.5 feet in length; most are sturdy performance-oriented boats-from the likes of Hallberg-Rassy, Beneteau, Jeanneau, Amel, Catana, Passport, Tayana, Hylas, and Hinckley-rather than ex-raceboat designs, and all are loaded with state-of-the-art navigation, communication, and liveaboard systems. I realize that there's not a Tahiti ketch or a shred of baggywrinkle to be found.

The start, gray and windless, goes off like the Oklahoma land rush. Throttles are floored as the fleet steams out of Chesapeake Bay to hollers and horn honks. Those new to rallydom, trying vainly to sail, are left behind in a weed patch of bouncing wakes and diesel smoke. Is this supposed to be a motorboat race? The answer is that by design, motoring is part of the Caribbean 1500; most years, the fleet ends up motoring 25 to 30 percent of the way.

"I don't want anything to stop boats from completing the passage in good order," explains Black, who says cruisers don't want to sit becalmed as unfavorable weather zooms in on them. In the Rally Class, where boats race in divisions with Caribbean 1500-assigned handicaps, engine time is penalized-motoring to victory isn't possible; motoring to defeat is more like it. Cruising Class boats aren't racing, and thus those skippers are free to motor all they want.

The first night, crossing the Gulf Stream is a breeze, beam-reaching in 15 knots with some lumps and bumps but no breaking seas. But the second night, a 25- to 30-knot pre-frontal southwesterly rag-dolls the fleet with squalls and square-topped seas and seems to set the tone for the rest of the passage: stiff breeze and boisterous seas, coming at you from uncomfortably far forward of the beam. The breeze is lighter for the next 36 hours, but gradually it shifts and fills in solidly from the east. Most of the fleet, which has made substantial easting by heading toward the suggested "Bermuda bailout" waypoint, is well positioned to straight-line it to Tortola. The next four to six days feature an unrelenting 20 to 25 knots blowing at 50 to 70 degrees apparent, enough 30-knot squalls to teach you not to shake out the reefs, and warm water exploding over bows, cabin tops, and dodgers. Conditions are testing but not tempestuous-breakdowns among the fleet include torn sails and broken sail hardware, steering glitches, and refrigeration, genset, and engine troubles. The things that can be fixed at sea get fixed. The unfixables are coped with, and the fleet soldiers on.