Colonia del Sacramento
Colonia del Sacramento is the oldest town in Uruguay, and one of the loveliest places on the whole river. Founded by the Portuguese in 1680 on the Rio de la Plata, directly across the water from Buenos Aires, it changed hands between the Portuguese and Spanish crowns again and again, and that long, contested history is written into every wall. The heart of it all is the Barrio Histórico, a small colonial quarter so well preserved that it earned a place on the UNESCO World Heritage list, and stepping into it feels like slipping a few hundred years back in time.
What makes Colonia so easy to fall for is the dreamy, unhurried mood of the place. The Barrio Histórico is a tangle of cobbled streets, none more romantic than the famous Calle de los Suspiros, the Street of Sighs, where worn stones run down toward the water between low colonial houses. There are plane-tree plazas to linger in, the old lighthouse to climb, the city gate and drawbridge to walk through, and sycamore-shaded cafes where vintage cars sit parked at the curb as if they have always been there. It is the kind of town made for wandering with no particular plan.
Best of all, Colonia is wonderfully easy to reach. A short ferry hops across the Rio de la Plata from Buenos Aires and drops you straight into the old town, or you can come by a scenic drive from Montevideo along the river. It makes a romantic day out or a gentle overnight, and we love folding it into a wider Uruguay journey, when the day-trippers leave and the lamplit streets fall quiet, it becomes something close to magic.