A one-hour ferry ride across the Rio de la Plate from Buenos Aires and few hours’ drive from Montevideo, Colonia del Scaramento is a Uruguayan town stuck in time. Anchoring the city is the Barrio Historico, the original, irregular street plan built by the Portuguese that is now a UNESCO World Heritage Site. Here, azulejo tiles cover the walls of centuries-old buildings and vintage autos take up most of the parking spaces – that are sometimes even used as planters. The once faded town, distinguished by its layers of architecture that formed as the town changed hands between the Spanish and Portuguese again and again, is slowly transitioning into the modern era without losing its charm. Instead of tacky gift shops, cafes and art galleries increasingly are becoming the norm. Get the best panoramic views of the town centre by climbing the winding stairs of El Faro, a lighthouse built in 1857 over the ruins of the San Francisco convent.

With its original stone walls and cobbled courtyard, Hotel La Mision is a 200-year old Spanish-built mansion, one of the several distinct boutique hotels in the town centre. More modern developments have been erected near the river, including the stylish Charco Hotel, which has seven individually decorated rooms outfitted with white leather armchairs and modern perks such as iPod docks. At Charco’s minimalist bistro, which incorporates produce from its own garden, you can sample gourmet versions of the iconic chivito sandwich made with filet mignon or salmon agnolotis with lemongrass cream. Or enjoy regional cheeses and traditional dishes made with products from the surrounding farmland paired with Uruguay’s palatable wines at Buen Suspiro, all while soaking in the cobblestone-laden Calle de los Suspiros. There is now even an artisanal brew pub in town, Barbot, with its own porters and Indian pale ales.

For even more serenity, the countryside beckons, and it is almost entirely undiscovered because many people skip Uruguay on their South American tour, visiting more popular countries like Argentina, Brazil or Peru. Just outside town is Bodega Bernardi, a family-run wintery that dates back since 1892, or stay the night at the rustic 12-acre ranch of El Galope, near Colonia Suiza, a unique community that blends the traditions of Uruguayan gauchos and Swiss German immigrants. Even farther from Colonia to the north is Carmelo, where the Four Seasons has a posh resort with locally inspired spa treatments and a par-72 golf course, not to mention access to some of Uruguay’s top vineyards.