Uruguay was the surprise of our 2019 South America trip. We went to Montevideo for what we thought would be a few days and ended up staying for almost the whole month of December, working remotely from a couple of different Airbnbs and slowly figuring out the city. We took the BuqueBus across the river from Buenos Aires — a three-hour ferry ride that's a small adventure in itself — and once we landed it just clicked.
Montevideo is calm in a way most South American capitals aren't. Walkable, safe, with a great food scene and almost no tourists relative to BA. Our go-to dinners were Terracota (modern, beautiful room, our favorite), BocaNegra Vinos & Tapas, La Perdiz for the parrilla, and Café del Puerto on the harbor. Say Cheese is a cute little spot for a light lunch. We did a food tour with a local guide that hit a bunch of places we'd never have found on our own — totally worth it.
The city itself doesn't have a single iconic 'must-see' the way Rio or Buenos Aires does — no postcard. It's more of a 'live like a local for a couple of weeks' city than a sightseeing city. Long walks along the Rambla (the seaside promenade), good coffee, the Mercado del Puerto for grilled meat, and the slightly sleepy energy of a country where the president famously gave away most of his salary. If you've got time to fit a quieter, gentler stop into a South America trip, this is the one.
We didn't get to Punta del Este on that trip, which is the next place we'd add if we go back.