I’ve been on both sides of the fence when it comes to cruising rallies. My very first transatlantic experiences, way back in 1992, were in two cruising rallies organized by Jimmy Cornell, the man who can rightfully lay claim to having invented the concept when he launched the Atlantic Rally for Cruisers (ARC), from the Canaries to the West Indies, in 1986. I’d be lying if I didn’t tell you I had a blast. Several of my closest sailing buddies to this day are people I met sailing in those events.

Later, when I was cruising the North Atlantic on a small boat of my own, spending as little money as possible, I tended to look down my nose at rally boats. I resented the space and resources they monopolized in key harbors and frankly was a bit of a snob about it. As in: real sailors don’t need baby-sitters holding their hands on a passage.

But anyone who has ever taken part in a rally will tell you it isn’t about babysitting. And anyone who has spent much time as part of the bluewater cruising community will also tell you that real sailors do hold hands and help each other whenever they can.

Since 1992 I’ve sailed in two other rallies. In 2002 I crewed aboard a large catamaran in the ARC and enjoyed myself immensely. Earlier, in 1998, I crewed on a boat in Steve Black’s Caribbean 1500 rally and probably learned more about heavy-weather sailing in one week than I have in all the years since then (see sidebar).

This year, for the first time, SAIL magazine is a sponsor of the Caribbean 1500, which means—once again—I get to sail in a rally. Again, I’d be lying if I didn’t tell you I’m rather excited about it. I’ve signed on to crew for Larry and Cathy Clough, a fit middle-aged couple who sail Katahdin, a well-found Cambria 44 that they keep on a mooring in Portland, Maine, not too far from my own boat. Though Larry and Cathy are veteran coastal cruisers, they’ve never been offshore before, and I look forward to re-experiencing, at least vicariously, the excitement of a first passage with them.

I also look forward to meeting the several other 1500 participants who will be losing their bluewater virginity this month. I’ve already spoken at length with Bob Woods, a doctor from Lexington, Kentucky, who will be sailing his Morris 46, appropriately named Lexington, with several fellow members of the Cave Run Sailing Association, a local Kentucky club. Bob and company may be neophytes, but rarely have I heard of anyone who has prepared so carefully and deliberately for a passage. I’m curious, too, to meet Mark Gorrell, who will be sailing offshore for the first time with his wife, Janet, aboard their Island Packet 465 At Last. According to Mark, the boat’s maiden voyage in 2007 was a boat test with a SAIL editor aboard.

The rally starts in Hampton, Virginia on November 7, and you can follow the event as it unfolds at carib1500.com/events/caribbean1500.html. I’ll also have a wrap-up for you in SAIL’s special bluewater cruising issue in February 2012.