We flew from Panamá City to Bogotá, and the moment we landed in South America it finally felt real our bikes and our adventure had officially crossed continents. After settling in, we explored the city, took in the incredible views from Monserrate, raced go-karts at a mall, and ended our first day in Colombia celebrating with food, friends, and a thunderstorm.

After an interesting Uber ride to the Overland Embassy, we met Ian an Irish rider living in Canada before heading to the airport to get our bikes through customs and ready to ship to South America. With the paperwork done, we split up to explore Panamá City some visiting the Panama Canal, others hunting bike parts and sushi before reuniting for Korean BBQ, drinks, and a final tequila with our bartender Gabby.

We rode from Penonomé to Panama City with our new friend Robert through beautiful farmland and mountains until a sudden tropical storm flooded the highway, forcing us to shelter our bikes under a tiny taco shop roof. After the rain passed, we delivered our bikes to be air-shipped to Bogotá since the Darién Gap stops the road between continents then celebrated our first night without them with good food, drinks, and some hilariously bad karaoke.

We crossed from Costa Rica into Panama after a smooth border process and rode through surprisingly lush, Jurassic-Park-like mountains until a motorcycle cop pulled us over in a small town. After he and Red saved a bike from tipping over and shared a hug instead of a ticket, we continued to Penonomé for sushi, drinks, and plans to meet a friend and ride into Panama City together the next day.

We left Puntarenas early hoping to beat the heat and traffic, filtering past construction delays on the bikes and stopping for a refreshing swim at a quiet national park beach before continuing south. Later, after getting pulled over for a risky pass and narrowly escaping $400 tickets when the officer’s system wouldn’t process our info, we rode the rest of the way carefully and reached the border town of Paso Canoas.

We celebrated one month on the road and a string of successful border crossings with a quiet day off in Puntarenas, a sleepy cruise port town on Costa Rica’s Pacific coast. After exploring beaches, planning the route ahead, and watching the sunset, it felt surreal standing in the ocean under the stars especially knowing we had ridden our motorcycles there all the way from Oregon.

Our ride from Managua to the Costa Rica border took us through beautiful, ever-changing landscapes, small towns with simple daily life, and the windy lakeside of Lago Cocibolca lined with towering windmills that pushed us sideways down the road. After a long 4.5-hour border crossing, we celebrated arriving in Costa Rica with a meal, rode on to Puntarenas, and ended the day with a perfect nighttime swim in the Pacific.

Running behind schedule, we decided to send it and head from Choluteca, Honduras to Managua, Nicaragua without successfully submitting the required border notice, unsure if we’d be turned away for seven days. Along the way a rider David Flores of the Osos Viejos MC guided us through the six-step border process, proving that riders really do look out for riders before we finally rolled into Managua and ended the day laughing over McDonald’s.

We crossed from El Salvador into Honduras, navigating confusing border offices, endless paperwork, and rumors that new regulations might keep us from entering Nicaragua unless we gave seven days’ notice and shipped our gear ahead. After hours of worry and a silent ride to Choluteca, a strong drink, good food, and a friendly local helped us end the day with a plan for getting into Nicaragua.

We left Antigua early after a tequila-heavy night and spent six hot, traffic-filled hours riding 200 miles through Central America, passing cars at speed bumps and losing time and money to a common copy scam at the El Salvador border. By evening we reached a cool loft in Santiago Nonualco, found good food and friendly locals, and ended the day laughing after discovering a chunk of metal stuck harmlessly in Red’s rear tire tread.

On our rest day in Antigua Guatemala, we finalized plans for Panama, performed preventative maintenance on the bikes, and explored the city’s historic churches, markets, and welcoming streets. After a great dinner at Brooklyn Pizza where we connected with fellow riders, it was time to turn in and prepare for our border crossing into El Salvador.

The ride from Huehuetenango to Antigua delivered exhilarating mountain roads carved into towering ridges, sweeping volcano views, and a breathtaking descent to Lago de Atitlán. After navigating chaotic traffic and cobblestones, we soaked in lakeside beauty, refreshed with iced coffee and a quick swim, then explored the vibrant, history-filled streets of Antigua.

Leaving 99.5% of Mexico behind, we wound through mountain roads into Guatemala’s lush canyons and finished day 23 in Huehuetenango with a great Italian dinner beneath four Oregon license plates hanging on the wall.

After extending our stay in San Cristóbal due to a weekend border closure, we unexpectedly witnessed celebrations erupt when cartel violence flared elsewhere in Mexico, then rode out in the rain Monday morning to complete a surprisingly smooth four-stop crossing into Guatemala.

Leaving 99.5% of Mexico behind, we wound through mountain roads into Guatemala’s lush canyons and finished day 23 in Huehuetenango with a great Italian dinner beneath four Oregon license plates hanging on the wall.

Blessed with the freedom to explore Mexico, we rode east from Salinas Cruz into the mountains to vibrant San Cristóbal de las Casas, where cobblestone streets, colorful buildings, rich history, and an unexpected border-delay extension gave us time to fully enjoy El Centro’s markets, bakeries, and nightly jazz.

Between cave hikes and zip lines at El Arcotete, sampling fiery Pox, and preparing for Guatemala, we soaked up every extra moment bittersweet to leave, but excited for the long road south toward Patagonia.

We rode east from Puerto Escondido into the Oaxaca highlands, climbing from swaying coconut palms to 9,000-foot forests of pine and cypress, winding through forgotten villages and steep, unpredictable mountain roads before landing in the funky charm of San José del Pacífico. After a Tuk Tuk ride, a few wrong turns into the unknown, and a triumphant return to civilization, we settled near Salinas Cruz for a quiet night by the beach, already plotting the next adventure.

We left our beachfront stay in Puerto Escondido and pushed south on Highway 200 through punishing heat, potholes, and traffic, only to abandon a sketchy “parking available” stay for a more secure spot after tempers and dehydration flared. Rehydrated and regrouped, we decided to trade the coast for cooler mountain air and set our sights on San José del Pacífico.

We left Acapulco on a hot morning and rode to a small beach near Cópala, eventually finding our stay at Puerto Bianco with the help of a friendly local. After settling in, our host Amber treated us to cold Palomas, a delicious dinner, and incredible hospitality that made for a perfect oceanfront evening.

We lost our Starlink an hour into the ride to Acapulco, backtracked to Playa Azul to retrieve it thanks to the incredibly kind staff at Hotel Posada Del Mar, then battled heat, breakdowns, and brutal Valentine’s Day traffic to finally arrive exhausted. What started as a frustrating day ended perfectly in a tiny dive bar where we were welcomed like locals, and closed out Day 14 with Spanish classic rock and new friends.

Day 13 brought another seven hours and 287 miles of hot, winding coastal roads, shaded by tunnel-like trees and lined with small towns, ocean views, and welcoming locals who patiently guided us through our Spanglish. After a round of hotel roulette, we found a spot near the shore that let us secure our bikes inside the gates, easing our minds for the night and ending the day by handing out flashlights and fidget spinners to a group of excited kids.

We rode south from San Blas tackling the winding, worn “free” coastal highway before stopping in Puerto Vallarta to exchange currency and refuel. By late afternoon we reached Punta Perula, checked into a secure hotel (avoiding goat-filled RV parking), rinsed off in the ocean, enjoyed a beachfront seafood dinner, and planned the next day’s ride.