Colonia del Sacramento, commonly shortened to Colonia, is the oldest city in Uruguay. Originally colonized by Portuguese settlers in 1680, it is full of hidden gems perfect for exploring on foot. The neighborhood of Carmelo is recognized as a UNESCO World Heritage site and has become an emerging wine-growing destination and is home to a number of boutique and luxury properties. Don’t miss the lighthouse at Convento de San Francisco for a bird’s-eye-view of the city. After you climb its 100-plus steps, indulge in a chivito, the national sandwich of Uruguay featuring sliced beef—one of the country’s identifying flavors!