IT'S EARLY FEBRUARY, and I'm sitting at home doing what many Americans are doing: feeling terrible for the people of Haiti and expressing it through the small, instant gesture of a $5 text-message donation.

I want to do more, of course, but I also recognize a fact that comes up every time there's a major natural disaster somewhere: I don't have any of the specialized skills—rescue, medical, logistical—that are really needed in these situations. While I can jury-rig a broken telemark binding just fine, I'm pretty much useless in an impact zone.

One morning, however, nosing around online, a story from Cruising World magazine's Web site causes me to perk up. An NGO called OceansWatch North America is organizing a flotilla of sailboats to deliver supplies to Haiti, and they need crew volunteers.

This I can do; I've got a bit of blue-water cruising experience. So I phone the CEO, a 60-year-old former meditation instructor and Aspen-based DJ named Sequoia Sun, vet him through a friend of his (a Greenpeace captain), and put my name on the list. Two days later, when another volunteer drops out, Sequoia invites me to take his place, and I happily skip to the front of the line.

Though I have a few small questions (Sequoia Sun? Aspen DJ?), I love the idea. Cut out the Red Cross–style overhead and the fat-bellied military cargo planes. Instead, stack a loaner sailboat with donated goods, gather capable people, and sail south to deliver relief. This direct, adventurous approach seems like a radical paradigm shift.

Which it is. But at times it will also turn out to be a big, radical mess, and there will be moments when I'll wonder whether I—and the world—would have been better served if I'd just stayed home and written a check.

ONE WEEK AFTER making the call, and a month after the quake, I find myself seated at a plastic picnic table in the backyard of a weathered bungalow in downtown Key West, Florida. We cruisers-with-a-cause, together for the first time, are finalizing our mission.

The boat we'll take is a stalwart 43-foot Westsail named Hiatus, its services donated by the owner, 58-year-old Captain Dan Wever, who's sitting beside me under rustling palms. Captain Dan sounds like a military officer, which he once was, in the Air Force. Across from him sits Sequoia, who looks uncommonly timid for a thickset man standing six-three. The two connected after Dan saw the same Cruising World piece I did, but they met for the first time just a couple of days ago.