Get your bearings in the Uruguayan capital with a walk along La Rambla, which takes you right around the watery edge of Montevideo from the portside banks of the Rio de la Plata to the breezy oceanfront vistas of the South Atlantic. Stop for lunch at Bar Tinkal, and admire the view while eating the city's best chivito – a signature Uruguayan steak sandwich piled high with cheese, ham, and other trimmings ($14, es-es.facebook.com/bartinkal). Also on the Rambla is Castillo Pittamiglio, a grand architectural curio designed by colourful local "alchemist" Humberto Pittamiglio (castillopittamiglio.com, tours $4, Spanish only). Wind your way back through the colonial old town to Mercado del Puerto, a Victorian wrought-iron structure lined with craft shops, bars and smoky parrillas (grill restaurants). There you can ease into the evening with a bottle of medio y medio (sparkling wine mixed with regular) at the 130-year-old Cafe Roldos ($12, roldos.com.uy) before a dinner of meat and fish-filled pastries at Empanadas Carolina ($10, carolina.mercadodelpuerto.com). Palermo Art Hostel has clean, quiet private rooms and a comfy roof terrace decked out with sofas and hammocks (doubles from $40, palermoarthostel.com).
EASY DOES IT
Load up with a breakfast of coffee and giant ham and cheese medialunas (savoury croissants) at Cafe Brasilero, a wood-panelled institution that opened in 1877 ($9, cafebrasilero.com.uy). The Sunday morning market along Calle Tristan Narvaja is a pageant of old-fashioned commerce founded by the city's first Italian immigrants, with books and clothes sold alongside fresh fruit and live animals (budget for $25, montevideo.gub.uy). A sunny summer day is best spent on the beach at Playa Pocitos, but if its wet and windy, you can hide out at Museo del Gaucho, amid the horsey artefacts of Uruguayan cowboy culture (free, no website, Avenida 18 de Julio 998). A football match at Centenario Stadium – home to both the national team and the beloved Montevideo club side Penarol – makes for pretty delirious entertainment (tickets from about $25, estadiocentenario.com.uy). Then repair to the cellar of El Lobizon for a few jugs of sangria or clerico (white wine with fruit) and a heavy plateful of gramajo – fried potatoes with eggs and ham ($40, ellobizon.com.uy). The top floor of the historic market building Mercado de la Abundancia hosts live tango sessions on Saturday nights ($15, facebook.com/MercadoDeLaAbundancia). You'll also want a top floor room at the old-world, wood-and-marble Hotel Palacio, to end the night on a private balcony with clear views over the old town (superior doubles from $70, hotelpalacio.com.uy/eng).
TOTAL: About $185.
La Abadia was once a Jesuit seminary and later the high-end tailor's shop where tango superstar Carlos Gardel bought his shirts. Today, it's an atmospheric stone-walled restaurant with the city's best breakfast menu ($20, no website, Ituzaingo, Montevideo 11000). Head just out of town for a tour of the vineyards at Bouza Bodega Boutique, a farm turned luxury winery, and stick around to sample the house vintage over lunch ($150, bodegabouza.com). When you get back to the city, you'll be well-primed to choose a decent bottle of local tannat or albarino at Museo del Vino, a great wine shop that hosts live tango in the evenings (budget for $50, museodelvino.com.uy). From there, it's a short stroll to a play, ballet, or opera at the grand old Teatro Solis, an 1850s vintage palace for performing arts with world-class acoustics (box seating from $70, see teatrosolis.org.uy). Uruguayans tend to eat late, so join the after-show diners at chef Gabriel Coquel's intimate fusion restaurant Tandory ($100, including wine, tandory.com.uy). Then spend the evening high-rolling at the gaming tables of the Sofitel Montevideo Casino Carrasco and Spa before retiring to a suite upstairs (from $350, sofitel.com).
Total: About $750.
The writer was a guest of the Palermo Art Hostel.