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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.

On the ferry heading back to La Gonave

On the ferry heading back to La Gonave

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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.

Already there's friction, and the problem is obvious: Both men want to be in charge. The rest of the gang? Near a recycling bin overflowing with beer cans sits a 34-year-old woman named Tory Field, the thoughtful, nose-pierced co-founder of a community-supported vegetable farm in western Massachusetts. Also coming along—but missing today because of a head cold—is Gino Muzio, a slender, 54-year-old infectious-disease specialist from Naples, Italy, who used to work with Médecins Sans Frontières (a.k.a. Doctors Without Borders). We call him Dr. Gino.

Our destination is La Gonâve, a peanut-shaped island of 75,000 that escaped the worst of the quake but, because of its relative good fortune, attracted a flood of refugees; we've heard rumors of 15,000 to 40,000 hungry and homeless mainlanders turning up there. Little international aid had arrived by late January, prompting CNN to air a short segment calling La Gonâve “the forgotten island.”

Maybe half an hour into the meeting, we fire up a pictureless Skype connection and buzz our on-the-ground contact: Father Soner, a Haitian Episcopal priest based in Anse-à-Galets, a town in eastern La Gonâve. He says locals are still struggling to feed and care for their displaced countrymen. Tent cities remain. The only functioning ferries aren't carrying food—incoming refugees are using up all the space—and water resources are strained to the limit.

“People are drinking water from the sea!” he tells us.

Our goal is to drop our food—three tons of rice, beans, and flour—with Father Soner. Then, for a couple of days, Dr. Gino will help out in the small local hospital, with me acting as his assistant.

How we're going to do all this is trickier than expected, because, even now, who “we” are is unclear. As the meeting progresses, I find out that Sequoia hasn't exactly been forthcoming. OceansWatch is not the lead organizing body of this trip but, instead, is piggybacking on a plan created by the Conch Republic Navy, a decades-old club of salty Key Westers. Turns out the CRN collected all the donations, chose La Gonâve as the destination, and organized a flotilla of six boats. Sequoia had told me we would sail at the head of as many as two dozen OceansWatch vessels, but it turns out that only Captain Dan and Hiatus answered the call. Now we'll be the lead boat in the tiny CRN flotilla.

The switcheroo doesn't bother me, since the CRN seems full of pros, having delivered aid to more than half a dozen Caribbean disaster zones over the years. The next night, aboard Hiatus, we plow ahead, poring over nautical charts until we come up with a mutually agreeable route. We'll go the relatively safe and slow Bahamian way: 800 miles, eight days, if the winds favor us, racing across the Gulf Stream, gliding down the shallow postcard waters of the Bahamas and Exumas, and dashing over the Windward Passage to La Gonâve.

On February 11, a Thursday, we tie up at Western Union Dock and load. On deck we lash jerry cans of extra diesel and cooking oil, along with 20 pairs of donated crutches. About a dozen volunteers dolly 50-pound bags from shipping containers parked nearby, handing them down Hiatus's companionway via human assembly line. Captain Dan supervises, stacking the bags like Jenga pieces in the boat's interior spaces. Meanwhile, he and Sequoia argue about Hiatus's seaworthiness with so much extra weight.

“That's all that's going on,” Captain Dan barks at one point. “We're eight inches below waterline.”

“I'd like to see a couple more bags at the bow, so it's level for sleeping,” Sequoia says.

I have no idea how much Hiatus can take, but I'd guess she's at capacity. When I try to open the door to the head, I have to yank hard three times before it pops free from its warped jamb—with a distinctive bwanggggggg.

ON SUNDAY, FEBRUARY 14, we hoist canvas. Chips ahoy! Adding to the excitement is a schooner-rigged CRN sailboat named Drummer, crewed by three young friends who've decided to join us.

I've grown to like loudmouthed Captain Dan, especially after he informed me that he once singlehanded the length of the Bahamas with nothing but a compass, a depth sounder, a VHF radio, and the invigorating fantasy of hooking up with nurses. Sequoia's résumé, on the other hand, remains a mystery, his most charming revelation being that the name on his birth certificate is John Wayne. But there's plenty of time to get to know everyone, I figure.

Or not. Around midnight, the crew of Drummer alerts us that the wind is shifting fast. Captain Dan wakes Sequoia to tell him we need to leave now if we want to make it across the Gulf Stream without getting hammered by tall standing waves.

Bad idea. You don't wake Captain Queeg and tell him you've changed plans. After days of bickering and delays, he snaps, yelling, “Fuck you, you fucking asshole!”

Captain Dan, menacingly quiet: “I want you off my vessel, body and possessions.”

Eventually, Captain Dan leaves the decision to the crew, and, like contestants on Survivor, we unanimously decide there can be only one chieftain, and Sequoia isn't it. At 4:30 A.M., with our boats idling a couple of miles offshore, I escort him and his coffin-size duffels toward the lights of Drummer, whose crew has no idea what just happened (because we don't tell them). The boat seems immeasurably lighter without him.

AFTER ARRIVING LATE in Nassau on Tuesday, February 16, we shove off as soon as possible the next morning, on a two-day run south toward Georgetown. With Captain Dan on the foredeck lookout, we surf downwind, the sandy seafloor skimming past just a couple of feet below. Whenever Dan spots a black island of coral in the spearmint-colored water, he raises a certain number of fingers and points to port or starboard, and I steer the same number of degrees in that direction. The patches of coral heads grow tighter as we get in sync, and soon we're slaloming along like a 20-ton rally car, with Drummer hours behind us. But when night falls, the wind shifts out from behind the bottom of the Exumas and—bam!—we're in a dead downwind run. Choppy seas. Tough sleeping. Sharing a comforter and tumbling from side to side on a bed of flour sacks, Tory and I pass out for six seconds at a time.

“It'd take years to get eight hours of sleep like this,” she groans.

We limp into Georgetown on Thursday, February 18. Drummer arrives some 12 hours later, and her exhausted captain decides to rest until the main CRN flotilla arrives, in a few days. Rubbed the wrong way one too many times by Sequoia, they also decide to kick him off.

Already short on time, we commence the final push alone the next morning, hoping for a single three-day tack southeast. The wind direction stays fairly steady, but the masthead anemometer spins 30 knots, or three times the NOAA forecast, and a disconcerting amount of seawater starts leaking in through our rudder housing. Unfortunately, there's no way to fix it while under way.

Trying to act as casual as possible, Captain Dan stuffs our passports and other essentials into an emergency bag in case we have to abandon ship. Tory pumps the bilge. Dr. Gino, at the height of what has turned out to be a respiratory infection, musters enough energy to opine, “I wish it was Monday.”

I find myself fatalistic and too nauseated to volunteer for the 4-to-6 A.M. watch, so I'm on the night shift. Night watches have their virtues—phosphorescents peel off the bow in a V, twinkling like stars—but I find them stressful, too. The globe-shaped compass glows red. Wind thrums across the sails in a low moan. The boat surges into blackness. The whole arrangement feels tenuous.

Not knowing more than a couple of Coast Guard light signals, I'm constantly confused. How close are those pinpoint lights, and are they trying to tell me something? Even after a $4,000, ten-day cruising course, I still can't figure that out. All I know is that the emergency beacon hanging on our tiller post flashes like Morse code, reminding me that A-N-Y-T-H-I-N-G C-A-N G-O W-R-O-N-G.

Soon, it does.

On Sunday, February 21, I wake to find that Otto, as I've nicknamed our ever-reliable autopilot, has burst a hydraulic line in the middle of the Windward Passage. Tory struggles to hand-steer, while Captain Dan, tools in hand, bangs around in a dark narrow hatch. Dr. Gino, utterly wasted, falls asleep between handing Dan paper towels to wipe away the squirting oil.

Half an hour later, right before Dan climbs on deck, justly triumphant at having somehow revived Otto, a red-and-white Coast Guard helicopter appears low on the horizon, maching toward us from Haiti, its jet turbine howling. They must've seen our erratic course on a high-powered radar, but we have no idea why they've come to save us. The State Department doesn't encourage or support private ventures to Haiti.

“Coast Guard helicopter, this is sailing vessel Hiatus,” I shout into the handheld radio.

“Go ahead, Hiatus,” it replies, hovering low off our mast, rotor wash riffling the water.

“Uh, I think we're gonna be OK,” I stammer, “but thank you so much for checking on us!”

“Roger that,” replies the deepest, calmest voice I've ever heard. “Coast Guard helo standing by on 16.”

TWENTY-FOUR HOURS LATER, at 7 A.M. on Monday, February 22, we've hit the calm waters of Haiti, gone for our first swim beside beautiful chalky cliffs along the northwestern peninsula, and arrived at Anse-à-Galets, La Gonâve.

Father Soner, whose bald head we recognize from a crinkled snapshot, steps forward from the dozens of silent locals milling about on the cement pier and greets us kindly. In no time, a string of young men unload what took us a full morning to get aboard. Soon after that, we're settled into the dorm rooms of the Episcopal Church compound. Now that we're finally here, the first thing I want to do is talk to Soner about how he will distribute our food.

Thankfully, it turns out he has a straightforward and trustworthy method. He and the police hand out dated chit cards to hungry families, register the distribution in a log, and then pass out the food in sequence from his secure compound. So far it's all in keeping with my fantasy—we arrived just in time!—but over the next few days, as I explore Anse-à-Galets and the outlying townships, I have difficulty squaring his initial description of La Gonâve with what I observe.

At first, I'm simply overwhelmed by new impressions. Loud church services. Goat­herds and lazy unattended pigs. Innumerable money-transfer centers guarded by men swinging shotguns. Beautiful white-stone beaches. Every pickup piled high with hitchhikers or 50-pound bags of something. A small kid in tattered shorts, wearing an oversize T-shirt that reads, in jaunty letters, YOU CAN'T AFFORD ME.

The island has no newspaper, so hard information is tough to come by, but the more I look around, the more Father Soner's old Skype descriptions seem off. People in Anse-à-Galets are not drinking water from the sea but from one of at least 16 public fountains, which appear to flow clear and cool. Ferries sail to the mainland daily and deliver, among other goods, large pallets of Coke. I don't see all of La Gonâve, but our situation appears almost absurd after Dr. Gino visits the hospital, which has 23 paid staff and, at present, a total of 20 patients.

“Where are all the refugees?” I ask Father Soner.

“They came immediately, two or three days after the earthquake,” he says. “When they came, they were not receiving good help in Port-au-Prince. But after a few weeks, they began to go back home.”

So how many are left? No one knows. But whatever the number, our roughly 6,000 pounds of food is comparatively insignificant. Between the quake and our arrival, the “forgotten island” received quite a bit of relief, it turns out.

In the week before our arrival, West Indies Self Help, a missionary-run, evangelical development organization based in La Gonâve, procured two shipments of food totaling 124,000 pounds. Lemon Aid, a Scottish charity (based in a former lemonade factory), brought 7,300 pounds of food and medicine. The sailors of the USS Bunker Hill, a guided-missile cruiser, brought MREs and thousands of gallons of drinking water. Members of the Wesleyan Church, an international evangelical congregation with local operations, procured 130,000 pounds of food and cooking oil. The Venezuelan government sent diesel fuel to run generators.

The list goes on. Supposedly, 36 other NGOs are at work on the island. And that's just what I've heard about.

Nonetheless, I'm glad I came. Father Soner might have overdramatized the situation, but he didn't maliciously bamboozle us. In one month, the CRN and OceansWatch have somehow made contact on a remote Haitian island, solicited thousands of dollars' worth of aid, organized volunteers, and gotten us safely here. I'm ecstatic not to find Gonâvians orange-haired with malnutrition but saddened to discover that our direct aid ended up so confused. Falling asleep at night, I struggle to find some sort of bigger takeaway.

TECHNICALLY, OUR MISSION is complete. Soon, Captain Dan and Dr. Gino will head for home, the jib and mainsail shredding in a gale near Jamaica and blowing out again near Florida. Tory will work the next month in a social-justice organization in Port-au-Prince. Sequoia will tell me later that he caught a ride out of Georgetown and distributed some aid to an island in southern Haiti. Feeling successful, he will confess that he'd never captained a sailboat more than 50 miles offshore and that his full legal name is—God's truth—John Wayne Edmister. (Not long after, I'll also learn that the board of Oceans­Watch North America has found that his actions “were not consistent with the desire or intent of the organization” and asked him to resign.)

Me? I detour to Port-au-Prince for two days. I'm exhausted, but after the confusion of La Gonâve, I have a deep desire to go to the epicenter, to see firsthand what a full-scale natural disaster looks like—and perhaps put our mission in better perspective. I ferry to the mainland, take a bus to the edge of the capital, and hire the first taxi that knows the location of the CNN compound, figuring I can talk my way inside if anything goes wrong. Hardly necessary. Guytho, the driver of the early-nineties Mitsubishi Lancer, turns out to be a champ. The 26-year-old father of two speaks almost no English but calls his 24-year-old buddy to translate. Osnel worked as a schoolteacher before the quake, speaks fluent English, and, when I find out that all the hotels are booked or broken, will secure us a place to sleep in a tent in the driveway of an abandoned NGO.

We spend the morning touring downtown—the palace, the church, random streets. The oft-reported smell of death has finally blown away on the sea breeze. The roads are clear, but the demolition has yet to begin, let alone the rebuilding. Afraid to stay inside their homes, seemingly everyone mills around outside. From the window of Guytho's not-so-fast taxi, we see tidy rows of tents and USAID tarps and shiny UN vehicles. Helicopters chopper overhead constantly. A long row of clean Sani-Can toilets shame those used at the New York City Marathon. I develop a new appreciation for Médecins Sans Frontières, which, alone among aid agencies, seems to hire lots of locals and operate on a shoestring budget. They'll slap a sticker on the door of a busted-up truck, give the badass driver a couple bucks, and call it an MSF tanker. Overall, the organization of aid appears impressive, at least for a capital not two months removed from a 7.0 earthquake.

Hungry, we pick up some bread, cheese, and tomatoes at the grocery store.

“Let's go to a park,” I suggest, imagining a picnic. Dumb. Forget about grassy fields. Any open space is full of tents.

Walking the less tidy outskirts in the afternoon, it becomes apparent that all is not perfect. Aid has not reached everyone in the north-central Delmas neighborhood, for example. Residents of those hardscrabble tent cities on hand-cleared lots complain about a lack of drinking water and worry that their lean-to's, made of bedsheets, won't hold up in the rainy season. Not wanting to be overlooked, they name their squats with cardboard signs: CAMP 003: WE NEED HELP.

In the early evening, we wind through a warren of alleyways talking to people who used to live in tight apartments.

“Koman ou rele?” I ask one woman in tentative Haitian Creole.

“Geurda,” she says.

Geurda is in her early twenties, with unflinching, streetwise eyes. She's standing by what looks like a hallway of rubble, no more than ten feet wide, with tabletop-size chunks of cement piled in a jumble. It used to be her apartment.

When the quake struck, her two-year-old was asleep in the front room beside her three-month-old, whom she'd just bathed.

“She was so afraid she couldn't move,” translates Osnel. “Then a lot of cement blocks fell on her and she couldn't move to save the children.”

“Has she received any help?” I ask.

“No.”

I'd like to ask what she needs, where she sleeps, if she knows anyone who fled to La Gonâve, etc., but when I launch into my thousand questions, she looks away. Osnel and I say goodbye and move down the alley. Clearly, she's not eager to talk. And, anyway, as Osnel informs me, we have many, many more people to meet.