Perched on the Rio de la Plata, the Uruguayan capital is like a trip through time back to another era — a vision of what Buenos Aires was like 50 years ago. One of the undiscovered urban gems of South America, Montevideo remains relatively small and extraordinarily friendly, a laidback Latin metropolis ready made for walking and ad hoc exploration.
What We Love
The Downtown Plazas: Perfect for lounging and people watching, the five squares of downtown Montevideo are located just a few minutes’ walk from one another along Avenida 18 de Julio and the Sarandí pedestrian street.
El Castillo Pittamiglio: Created by an eccentric Uruguayan architect, this flamboyant mansion in the Punta Carretas district combines Gothic, Renaissance, and Iberian design with Masonic, Templar, Rosicrucian, and even maritime motifs.
Best Known For
Beef: Like its urban alter ego (Buenos Aires) on the other side of the estuary, Montevideo is renowned for excellent beef. The steak served at the city's “parrillas” (grilled meat restaurants) is every bit as tasty as what you'd find in Argentina — especially when paired with Uruguay's excellent red wines.
Beaches: While not quite as chic as Punta del Este two hours to the east, Montevideo's sandy shores are nothing to sneeze at. High-rise-lined Pocitos is the most renowned, but there's better swimming out east at Atlántida.
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Who It's Best For
Romantics: The old buildings, the breezy plazas, the tango music, the moody restaurants — Montevideo flaunts an old-school romance that is quickly fading in other parts of Latin America.
Walkers: We're not talking zombies from the “The Walking Dead,” but rather anyone who loves to explore a city on foot — a feat (no pun intended) expedited by the city's many plazas and pedestrian streets, like Pérez Castellano and Sarandí.
Don't Say We Didn't Warn You
Beware the Cubierto: Many restaurants in Montevideo have a mandatory cover charge called the “cubierto” that can run anywhere from 10 to 35 pesos per person. But don't freak out; even with this cover charge, overall prices are very reasonable.
What's Legal Onshore May Not be Allowed On Board: Marijuana might be quasi-legal in Uruguay, but don't be tempted to bring it back onto the ship — possession might be a felony at your next port of call.
Joe Yogerst is a California-based contributor to ShermansCruise who has also written for Travel + Leisure.