Set off to charming Colonia del Sacramento, a UNESCO-listed town built by the Portuguese on the bank of the Rio de la Plata. Spend a day wandering down its cobblestone streets, discovering colorful clay houses, colonial bridges, quirky museums, and views of the river as far as the eye can see.

Following pickup in Montevideo, head west along the bank of the Rio de la Plata, taking in sights of idyllic farmlands along the way. Just before reaching the heart of Colonia, stop for a visit to the Granja Arenas, a complex that houses a museum, restaurant, and sweet factory. Step inside to see sprawling collections of pencils, perfume bottles, and matchboxes, and sample hand-crafted jams made with pumpkin, pears, and figs.

Upon arriving in Colonia, your first stop is the Real de San Carlos, a crumbling arena that once hosted bullfights in the early 1910s. From here, embark on a walking tour of the historic center of the city. Stroll down romantic alleyways to uncover pastel buildings, quaint cafes, and an 18th-century drawbridge that was once protected the city from enemies. Before returning to Montevideo, climb to the top of Colonia's famous lighthouse for panoramic views over the river.