Few dare attempt the challenge of riding the entire Americas on a Royal Enfield Classic 500. It takes patience, grit, and a deep appreciation for the unknown. For Diego Rosón, an Argentine traveler and photographer, this journey is an ever-evolving story shaped by the landscapes, the people, and the road itself. His expedition from Ushuaia to Alaska has unfolded in carefully planned stages, each filled with trials, triumphs, and the kind of experiences that only long-distance travel can provide.

For those just joining his adventure, Diego’s odyssey began at the southernmost city in the world—Ushuaia, Argentina. He has already ridden through Patagonia’s relentless winds, climbed the towering peaks of the Andes, and crossed South America’s vast, untamed landscapes. Now, he embarks on the third stage of his expedition, departing from Bogotá, Colombia, with Los Angeles, California, as the next milestone. The road ahead will take him through the heart of Central America and Mexico, regions that promise both challenge and beauty in equal measure.

This chapter follows the first half of his journey northward, from Bogotá to Mexico City, a stretch of road where bureaucratic red tape, mechanical setbacks, and unforgettable encounters define each mile. With Frankie, his trusted Classic 500, as his companion, Diego pushes forward, chasing the dream of reaching Alaska—one mile at a time.

The Third Stage Begins:
Bogotá to Mexico City

After two and a half months off the road, Diego Rosón lands in Bogotá, eager to reunite with Frankie, his Royal Enfield Classic 500, and continue his journey. The motorcycle, stored at Royal Enfield Campin, received much-needed TLC under the care of Alex, the shop’s chief mechanic, who had kept Diego updated on its progress.

“I know it’s not a living being, but I swear I almost teared up when I saw her. It felt like she wagged her tail like a loyal dog greeting its owner.”

Spending the day at the workshop felt like home—the camaraderie, the shared passion for motorcycles, and the warmth of the people made it hard to leave. But there was work to be done before Frankie could be shipped to Panama to cross the dreaded Darién Gap.

Amid conversations and handshakes, Diego added key upgrades:
✔ A new windshield, gifted by his friend Willy after the original shattered in Chimbote, Peru.
✔ A conical K&N air filter for better performance.
✔ A wireless charging phone mount for seamless navigation.

Despite the excitement, time was running out. The next day, he had to be at Bogotá’s El Dorado airport to begin the long, bureaucratic process of flying his bike to Panama.

As he stepped onto the tarmac, anticipation surged through him. “My heart raced past 55 mph (90 km/h) when I realized the road of my dreams was about to cross paths with reality.”

Panama City & The Road Ahead:
A Journey Begins

Though Panama City wasn’t seen in a mile of his journey, it earned a place in his itinerary. A city of contrasts—colonial and modern, tradition and technology, wealth and poverty—its unique duality fascinated him.

He spent the morning cycling along scenic paths past exclusive marinas before heading to the Miraflores Locks. The Panama Canal, inaugurated in 1914, was an engineering marvel built long before modern machinery. Initially attempted by the French in 1880, the project was abandoned after 20 years and 20,000 lives lost to disease. The U.S. took over, and by August 15, 1914, the canal was open, revolutionizing global trade. Today, transit fees range from $150,000 to over a million dollars, making it cheaper than rounding Cape Horn.

By midday, he wandered through the bustling Mercado de Mariscos, a feast for the senses, though his seafood allergy kept him from indulging. From there, he explored the historic district’s cafés and colonial plazas before strolling the Malecón, a lively 3 miles (5 km) stretch where locals ran, cycled, and enjoyed the afternoon breeze.

A message lit up his phone—his friends Eugenia and Nacho lived nearby and invited him for dinner. Over Chinese food and wine, the night flew by with laughter and stories. By 11:00 p.m., he hurried back to his room. Tomorrow, at 6:00 a.m., the real adventure would begin.

Motorcycle travel adventure: Diego Rosón and his Royal Enfield Classic 500 on a scenic road through Central America.

Panama City & The Road Ahead:
A Journey Begins

The tide’s gentle rocking woke him before dawn. Suspended on stilts above the sea, the peacefulness was precisely what he needed. Stepping outside in just swim trunks—unthinkable in Patagonia—he realized they might become a staple for this leg of the journey.

Packing light, he took only his camera gear, sensing the day would bring something new. A bus ride to Playa Drago and a short walk led him to Playa Estrella, home to countless starfish beneath the crystal-clear waters. As he wandered, a group of Uruguayans pointed up—two sloths lazily hanging from a tree. “I HAVE NEVER SEEN SLOTHS BEFORE! AH!” Excited, he reached for his Canon M50 with a 28-300mm lens—heavy but worth every gram.

Ricardo, a beach vendor passionate about his land and its sloths, was blown away by the photos and offered a trade—his snorkeling gear for the shots. Just 60 feet from shore, a glowing galaxy of starfish stretched across the seabed, their slow movements mesmerizing.

Motorcycle travel in Nicaragua: Diego Rosón riding through volcanic landscapes on his journey to Alaska.

Reality Check &
The Road to Costa Rica

Many assume this journey is effortless. They’re wrong. Three days in, his clothes still wouldn’t dry, drenched from sweat, rain, or humidity. Each morning began with a damp shirt, and by the time he reached the dock at 6:00 a.m., hauling his heavy bag, the last clean one was already soaked. A sudden downpour masked the worst of it. “Chipy can rest easy—no one’s coming near me. I’m disgusting.”

Bocas del Toro faded as he reached Frankie, who was waiting in the parking lot. By 7:00 a.m., he was rolling toward the Costa Rican border. Just 45 minutes later, he crossed into the land of his brother-in-law, Diego Estrada, who, ironically, was riding a motorcycle through Argentina.

Only 83 miles (133 km) were covered that day—progress in Central America felt painfully slow. After settling in, he rode to the Gandoca-Manzanillo National Refuge through coastal villages. Being a Sunday, the crowds had scared away the wildlife. “Sometimes, I think we deserve extinction.”

His next stop is a rusting shipwreck, feeding his fascination for abandoned places. When he arrived, the sight was breathtaking—a decaying hull, a monument to time, framed perfectly for his camera.

By 3:30 p.m., hunger reminded him he hadn’t eaten all day. He found salvation in a Rasta bar, where ribs sizzled on the grill to Bob Marley’s rhythm. “Everything right in the world was happening in this place.”

Across Costa Rica:
From Jungle Trails to Surf Towns

He checked the tide charts for Manzanillo, hoping to photograph the beached ship at low tide, just as he had with the Desdémona in Tierra del Fuego. Low tide was at 6:00 a.m., the perfect excuse to escape his relentless mosquito companions. Stepping outside, the town was unrecognizable compared to the previous day—calm, pristine, free of crowds. It was a chance to rediscover its beauty in peace.

Reaching the shipwreck, he found the tide higher than expected. Without dwelling on the setback, he embraced the morning’s tranquility before returning to the hostel for breakfast and another day on the road. His first stop was Cahuita National Park, where a quiet Monday promised serenity. The three miles trail initially seemed uneventful—a beautiful beach, but nothing remarkable. Then, the jungle came alive. Monkeys, raccoons, hermit crabs, exotic birds, and vibrant butterflies filled the path. “This could have easily inspired Avatar.” His planned two-hour visit turned into four as he lost himself in the scene.

Back on solid ground, the heat and exhaustion hit. Sweat-soaked and burdened by his camera bag, he craved a pineapple smoothie. A quick swim reset him before being fully recharged for a meal.

By afternoon, he set off for San José, crossing the mountains again. The heat tempted him to ride without extra layers—a mistake he regretted when rain and fog rolled in. “Humans are the only creatures that trip over the same stone twice.” A five-minute stop to put on rain gear would have saved hours of discomfort, but stubbornness won. “I know the theory—I just need to practice it.”

By nightfall, drenched but satisfied, he reached San José, where he reunited with his sister-in-law Agustina over mushroom risotto and wine. He booked his morning ferry from Puntarenas to Paquera, the gateway to the Nicoya Peninsula.

Wild Costa Rica:
Rivers, Roads & Volcanic Secrets

The plan was to start the day with an early surf session before heading to Tamarindo. Everything was ready—except fuel. Luckily, he had asked beforehand. “No, Don! There’s no gas here.” That simple answer forced him to abandon his surf plans once again.

The nearest station was in Cóbano, a 30-minute detour in the opposite direction. It was frustrating, but this was a motorcycle journey, not a surf trip. An hour later, he was back where he started—tank complete, swim trunks dry, ready to leave Santa Teresa behind.

He headed north along a rough coastal dirt road, potholes and dust coating him for hours. But the reward was worth it—Playa Hermosa, Manzanillo, San Francisco de Coyote, and Sámara. By midday, the heat and dust were unbearable. He needed water. His feet ached inside his boots.

Then, as if answering his plea, the road ended in a river—100 feet (30 meters) of water stood between him and the other side. He assessed the depth: knee-high. It was manageable, but alone, it felt like an ocean.

He unloaded his gear, lightening the bike. First gear, roll in. The loose stones made traction unstable, but Frankie pushed on. Halfway through, the back wheel slipped, sinking into the sandy riverbed. Instinctively, he leaped off, landing to the left. Feathering the clutch, he regained control and pulled the bike free.

Three river crossings later, now damp and confident, he pushed on, opting for the faster inland route to meet his friend Martín Salerno in Tamarindo. They caught up over a salad and yet another pineapple smoothie—his new obsession.

Though just 60 miles (100 km) remained, distances felt longer in Costa Rica. By sunset, he reached a tranquil mountain retreat near Rincón de la Vieja National Park, where tomorrow’s adventure awaited.