Explore Montevideo’s vibrant Old City (Ciudad Vieja) and colonial past, or head out to a winery and sample a smooth Uruguayan vintage. In Santos, Brazil and relax at Gonzaga Beach, which resembles a resort on the French Riviera, or set off for São Paulo’s cultural sites, including the Pinacoteca do Estado de São Paulo museum. On Ilha Grande, disconnect from the world and soak up the sun on the picture-perfect Lopes Mendes Beach.