After meeting in sensational Buenos Aires, hop a boat across the vast Río de la Plata to enter Uruguay • Wander the colorful cobblestone streets of waterside Colonia del Sacramento, known for its World Heritage old town • Dine among the vineyards at Uruguay’s oldest winery • Ride along the Río de la Plata’s edge, where sky and river stretch into infinity • Get out on the water on a sunset cruise • Sit down to a candlelight dinner at a refined wine lodge.

Enter Montevideo, Uruguay’s vibrant capital, by bike • Sample sizzling dishes at bustling Mercado del Puerto, tucked into a vintage wrought-iron structure reminiscent of a Victorian railway station • Meet a Candombe drum maker to get in sync with Uruguay’s Afro-Latin heartbeat • Pedal the city’s iconic seaside boulevard, the Rambla • Spend the evening exploring Montevideo’s charming neighborhoods and nightlife. 

Explore vintage beach towns and windswept dunes by bike, then ascend coastal foothills with 360-degree views • Arrive at our remarkable hilltop getaway, where you’re treated to a tour of the property’s private art collection • Take a break from the bike to stroll the grounds of a contemporary sculpture park • Try yerba maté, the caffeinated national obsession that Uruguay shares with its neighbors • Sit down to a traditional asado cookout in the forest • Spin through hills covered with century-old olive groves and blend your own signature oil in a hands-on experience. 

Spin through reedy wetlands teeming with native birds and stoic, adorable capybaras • Check out the galleries in a sleepy artists’ village • Give your trip a proper send-off with a farewell feast on the beach • Stretch your legs before your onward travels with one last spin to an iconic lighthouse.