The Pan-American Highway runs nearly 30,000 miles from Prudhoe Bay, Alaska to Ushuaia, Argentina. Just about midway, there's a 50-mile obstacle known as the Darien Gap. It's an impassable tangle of jungle and swamp between Panama and Columbia. A dusty parking lot outside an unmarked customs office in Panama City is the first stop for anyone determined to follow the Pan-American Highway from Central to South America. The road ends three hours east of here at the Darien Gap, where even some of the most rugged off-road adventures have tanked. My wife and I found fellow-travelers Lindsay Madson and Brian Ronstadt by posting an invitation online to split a 40-meter shipping container. Ronstadt and Madson drove from Portland, OR, with plenty of guidebooks in a van they named Claudette, equipped with a bed and a basic camp stove. It's a real throw-back. You half expect to see a bumper sticker saying something like, "if this van's a rockin', don't come a knockin'." "Claudette is dirty and tired, but I think she'll get us to Colombia," Ronstadt said. The customs inspector shuffled over from the far side of the lot. No identification. No uniform. "Any official with a Bob Marley shirt is someone I'm happy to do business with," Ronstadt said. The official requested the vehicle titles and a handful of other documents. Inspector: "El certificado, titulo de properdad?" Ronstadt: Tengo aquí. Inspector: "Y la copia." Zachary Slobig: "Aduana?" Inspector: "La copia, es un original." Slobig: "Necesitas una copia de este? I don't think we have a copy of that." We've driven across six international borders on our trip so far. At each stop there's been some additional document that needs copying. Fortunately, there's always a copy machine nearby. My wife found one across the street inside a deli cooler next to a stack of plantains. The next day we were off to the port city of Colon, an hour drives north. One guide book advises to avoid Colon "unless you relish the possibility of a mugging at knife point." At 10 am, we're waiting on a street corner just outside the gates of the city's 40-square-block duty-free zone to meet Boris Jamarillo, our shipping agent. Jamarillo arrived and led us to the Colon customs office for more paperwork. "We need to make a set of the documents," Jamarillo said. "Here we need two or three documents only. For the port we need more, but for the customs, two or three, including the original." Jamarillo has become known on web message boards as the 'go to' shipping agent in Colon. It's not a niche he sought, but travelers continue to rely on him. "This is not my business, my principal business, but in the beginning somebody said to me, please help me. The messages say that he know what they need to do, so from this time I help many people," Jamarillo said. "It's because you are the best in the entire country of Panama," our traveling partner Brian Ronstadt said. "That's what they say on the internet." We caravanned to our next stop, the port inspection area. Here we found two Volkswagen vans waiting for shipment, also clients of Jamarillo. Andres Lindver, an Estonian living in Canada, proudly rattled off his long-distance driving adventures. "Last year Alaska was a big one, 21,000 kilometers," Lindver said. "I've done Russia a lot, all Canada, all the states. It's pretty cheap, it's flexible, it's very convenient." The port inspector arrived and we unloaded our vehicles for inspection by Judy, the drug-sniffing retriever. With the inspections complete, each traveler counted out a small pile of cash for Jamarillo and watched port workers drive their vehicles towards the docks. Ronstadt and Madson's van started up, rolling away, horn honking. Travelers have two options at this point: take the quick flight to Cartagena, or sail there over several days by way of the San Blas islands. We chose the latter, as did Ronstadt and Madson. We booked passage on separate ships and planned to meet up in Cartagena. My wife and I made our way to the blue Caribbean waters of Puerto Lindo, where our boat, the Tres Amigos — really, that's the name — was anchored. In Puerto Lindo, we found our Captain Bryan Berc, and bad sailing conditions. "We've got northeast winds today, 15-20 knots with some higher gusts," Berc said. "Seas are three and a half meters coming down from a four-meter swell." We waited four nights for the system to pass. On the morning of our fifth day, we raised the sails and made a go of it. "Today will be an adventure, that's for sure," Berc said. "It's pretty rough out there. I have no problem sailing in these conditions. It's a very strong boat." A mile farther out to sea, though, our captain's bravado had flagged. "I think the best thing is just to hang out another day, wait for the weather and if people decide they don't want to go, that's cool, there'll be some refunds," Berc said. We decided to jump ship and found our way to nearby Puerto Bello for the night to arrange for air travel. The next evening we were on a 46-minute flight to South America. We found Brian Ronstadt and Lindsay Madson in their Cartagena hotel courtyard the next day. They had sailed successfully, if not entirely comfortably. The last 36-hours of open ocean to port had been rough. Madson: "We have definitely realized that we are land lovers." Ronstadt: "It was a challenge." Madson and Ronstadt: "Or as we like to say, an opportunity." After a trip to the shipping company office, we paid our release fees, and spent a long morning in a sprawling customs office. Official: "Importacion temporal?" Ronstadt: "Importacion temporal, si" Official: "Tourismo?" Slobig: "Turismo, si" We completed yet more paperwork and were assigned an inspector who never arrived. Then we were sent to the Port Authority to meet with our final gatekeeper in the process, Pablo Uribe, who outfitted us with the proper safety equipment to enter the port. Uribe: You have long pants and closed shoes, and I'm gonna give you, how you call this? Ronstadt: "A helmet." Uribe: "A helmet and a reflective…" Ronstadt: "A vest?" First, of course, yet another round of documents. A couple of bureaucratic steps and hours later, we were escorted through the bustling backyard of the port, past its belching big rigs and halting forklifts, past the dock where the cruise ships unload into a grove of trees filled with chattering parrots, and finally to a lot even dustier than the one where we began our journey in Panama City. "Hey, there they are. Yeah, the tires still have a little air in them," Ronstadt said. "Awesome." Back behind the wheel, our journeys continued down the winding Pan-American Highway towards the equator.