Colonia del Sacramento was founded by the Portuguese in 1680.
It’s the first port of call for tourists sailing across the Río de la Plata from Buenos Aires.
The town’s cobbled lanes and colonial one-storey casas evoke the old-world feel of Lisbon.
La Calle de los Suspiros (the Street of Sighs) is perhaps the town’s most enigmatic spot. It’s rumoured that prisoners lingered here, waiting to be drowned in the river at high tide.
Look out for Colonia’s cosy wine bars, tucked away on the cobbled streets of Barrio Histórico, for a bottle of fine local tannat.
For the best views of the bay, climb the lighthouse for a small fee.
Stop by the 18th century Puerta de la Ciudadela, a city gate that stood firm throughout a century of war.
Spanish guitar and cocktails unite at Colonia’s coolest drinking den: El Drugstore.
All aboard for dinner at the town’s Restaurant Del Ferrocarril, set in an abandoned train carriage.
Trek a little further afield to explore South America’s sole bullfighting ring, Plaza de Toros Real de San Carlos. It went out of business after just two years when bullfighting was outlawed in 1912.
Uruguay’s oldest church, Iglesia Matriz, can be found at Plaza de Armas, near the riverfront.
Budding artists shouldn’t miss Granja Colonia Arenas, a quirky museum housing more than 15,000 pencils, among other stationery memorabilia.
Car enthusiasts, keep your eyes peeled: Colonia is home to some picture-perfect vintage motors.
Grab a bite of fresh local seafood at one of Colonia’s many habourside cafés. Parrilla Santa Rita is one of the best.
Head down to the riverfront at dusk – it’s a custom in Uruguay to applaud the setting sun.