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A cobblestone Portuguese-Spanish border town, a jet-set beach resort, and a village with no electric grid.

Colonia
A UNESCO-listed colonial town of cobblestone streets founded by the Portuguese in 1680, a favorite easy day trip by ferry from Buenos Aires.
Hotels from ~$30-90/night

Montevideo
Montevideo's old town, a grid of Art Deco and neoclassical buildings along the Rio de la Plata, with a laid-back pace unusual for a capital.
Hotels from ~$30-90/night

Punta del Este
South America's answer to the Hamptons, a glossy beach resort of high-rises and marinas that fills up every South American summer.
Hotels from ~$60-200/night

Rocha
A remote dune-backed village with no electric grid or paved road access, reached only by truck across the sand, home to a large sea lion colony.
Hotels from ~$20-60/night