FROM ACAPULCO SOUTH to the Guatemala border lie hundreds of miles of yellow-sand beaches, from the surf towns of Puerto Escondido and Puerto Ángel to the undeveloped coast of Chiapas, where you might see a few palm-frond-roofed palapas and then another 100 miles of nothing. Conventional sailing wisdom advises keeping close to land here as you pass through the enormous Gulf of Tehuantepec: They say the "Tehuantepeckers," 60-knot winds that scream across the narrow, flat spit of land separating the Gulf of Mexico from the Pacific, can blow you 300 miles to sea. This is myth, in my experience, but the sailing world is full of myths, and this one puts every yacht in close to shore, where it becomes a target for pirates.

The pirates of southern Mexico don't quite merit the name. Those off the coast of Somalia have .50-caliber machine guns and rocket-propelled grenades. They operate out of a country that hasn't had a stable government in more than a decade, so they are in fact much like the 17th- and 18th-century pirates of the Caribbean, powerful enough to capture entire ports and operate out of them untouched. The pirates of most of the world, though, and certainly the Central American coast, would never think of themselves as pirates per se; they are merely opportunists, poor fishermen and petty thieves. A passing yacht can be worth a hundred times what a Mexican fisherman will make in his lifetime—when I was here ten years ago, the average wage was $25 a month.

Add in the fact that this coast sits right on an active smuggling route. Acapulco lies between the Colombian port of Buenaventura and California, and with crackdowns in the Caribbean, smugglers have moved out into the Pacific, its vastness hiding merchant ships towing submarines full of cocaine, cigarette boats running fast and invisible to radar in the dark, semisubmersibles riding low, only their periscopes sticking up. In October 2007, Mexican law enforcement seized 23.6 metric tons of cocaine from a ship docked in Manzanillo, a record seizure on land or at sea. It was just outside Manzanillo that Long had his first brush with pirates. He'd made it all the way down the 1,100-mile coast of Baja California and stopped for a few repairs in Mazatlán. But just north of Manzanillo, at sea, at night, his electrical system died. His alternator was out. He also had a recurring mechanical problem: The prop shaft would slip back and jam against the rudder and make him go in circles.

Long set off his EPIRB, which alerts rescue agencies by satellite. This is a serious piece of equipment, an international cry for help that should not be set off unless the boat is sinking or there's some other life-threatening emergency. Problems with an electrical system don't usually qualify. But Jason says his father was worried that without power, he wouldn't have lights or radar and was in danger of collision.

The Mexican coast guard came out immediately. They'd been watching Long, because sitting there in one place with his lights off, he looked as if he were on a drug rendezvous. The officers boarded with machine guns and made him leave his boat. Then they sped away, leaving the Cúlin drifting, and stopped and waited. Pirates were tracking the boat, apparently. "It was kind of left as bait for a while," Aaron says. The coast guard watched on radar, but the pirates had radar too, and they could see the coast guard waiting, so they turned back. The officials returned Long to his boat and gave him a free tow into Manzanillo, and there he began an ordeal of repairs and scams and paperwork that lasted more than a month.

When Long finally left Manzanillo, in January, he planned to sail straight to Panama. He continued to have mechanical and electrical problems, though, so Aaron thinks he may have been looking for a port to pull into for repairs. He was hugging the shore, sailing no more than a few miles out, avoiding the Tehuantepeckers. This put him right in the drug route, not only for big loads to Acapulco but also for local traffic making quick trips over the Guatemala border. He presented an opportunity to everyone.

The ironic thing is that Long had built the Cúlin specifically to withstand pirate attacks. He'd placed his helm inside and could lock himself behind a massive sliding steel door and windows of thick bulletproof glass. All his lines to control the sails ran inside as well. I've never seen or heard of another sailboat quite like this. Most sailors just hope they won't run into pirates, but Long was prepared.