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The Caribbean 1500 fleet is ready. The workshops—on offshore safety, fuel, water, food, seasickness, navigation, passagemaking strategy, weather, the Gulf Stream, diesel troubleshooting, fishing, circumnavigating, and the ladies' roundtable—are concluded. The demonstrations and presentations—of life rafts, flares, weather reports via e-mail—are over. Safety inspectors have been in and through each of the 45 rally boats; the shuttle-bus runs to West Marine are winding down. Even the crowds at the dinners and cocktail parties in the main tent have thinned out—most crews are busy squirreling away last-minute provisions or studying the Gulf Stream's latest wiggles for the 1,280-mile passage from Hampton, Virginia, to Tortola, in the British Virgin Islands. The rally fleet is ready—but the weather isn't

With a powerful low-pressure system churning northeastward up the Eastern Seaboard toward the Virginia coast, Caribbean 1500 founder and impresario, Steve Black, who presides over the event with the folksiness of Garrison Keillor and the wisdom gleaned from managing 18 previous rallies (he's sailed in 14 of them), chooses to delay the start five days to let the gale pass by. A November passage from the U.S. East Coast to the Caribbean, as veteran cruisers and delivery skippers will tell you, is tricky: Dodge the early season winter storms, negotiate the mercurial Gulf Stream, and find favorable breeze for as many days as possible all while keeping an eye out for post-season hurricanes forming in the tropics.

Black works with a team of meteorologists at Commanders' Weather, a forecasting service, to pick the best weather window for the rally, and he keeps the fleet updated with a daily briefing. As the new jump-off day approaches and the warm waters south of Cuba brew up Hurricane Paloma, Black and Commanders' Weather decide to route the fleet well east of the rhumb line, to within a day's sail of Bermuda—a prudent bailout plan should Paloma make it past the cold water and cold-air masses north of Cuba. After an additional one-day delay to allow the post-gale 10- to 14-foot seas outside the Chesapeake to subside, the rally is ready to roll. Meanwhile, crews have kept busy with their preparations, perhaps also pondering the realities of passagemaking in company: What are the pros and cons when you choose to sail with the herd?

Certainly, anti-rally cruisers are quick to point out that "safety in numbers" is an illusion; once at sea, you're on your own. Nevertheless, do folks joining the Caribbean 1500 expect to have a safer passage? "It's not the proximity of other boats but the commonality of purpose that's the most valuable aspect of the event," says Black. "You're able to get troubleshooting help and immediate answers to your questions about equipment, weather, and how to make a passage—right down to how to properly secure a tender on deck or in davits. And you get the added benefit of a safety inspection by a veteran offshore sailor."

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