Brazil, Uruguay, Argentina

Uruguay’s capital city hugs the eastern bank of the Río de la Plata. A massive coastal promenade (malecón) that passes fine beaches, restaurants, and numerous parks recalls the sunny sophistications of the Mediterranean and is always dotted with Montevideans strolling, exercising, and lounging along the water. Montevideo has its share of glitzy shopping avenues and modern office buildings, balanced with its historic old city and sumptuous colonial architecture, as well as numerous leafy plazas and parks. It is hard not to draw comparisons to its sister city Buenos Aires across the river, and indeed Montevideo strikes many as a calmer, more manageable incarnation of Argentina's capital.When the weather's good, La Rambla, a 22-km (14-mile) waterfront avenue that links the Old City with the eastern suburbs and changes names about a dozen times, gets packed with fishermen, ice-cream vendors, and joggers. Around sunset, volleyball and soccer games wind down as couples begin to appear for evening strolls. Polls consistently rate Montevideo as having the highest quality of life of any city in Latin America. After one visit here, especially on a lovely summer evening, you probably will agree.

Glamorous and gritty, Buenos Aires is two cities in one. What makes Argentina's capital so fascinating is its dual heritage—part European, part Latin American. Plaza de Mayo resembles a grand square in Madrid, and the ornate Teatro Colón would not be out of place in Vienna. But you’ll know you’re in South America by the leather shoes for sale on cobbled streets and impromptu parades of triumphant soccer fans. Limited-production wines, juicy steaks, and ice cream in countless flavors are among the old-world imports the city has perfected.