Haven't been to Punta del Este, but heard good and bad about it. Passed through Montevideo for a day and I really liked it to be honest. It's probably the most chilled-out capital city I've ever been in. Parts of it are a bit run-down and a lot of places need a lick of paint, which in my opinion gives it a fair bit of rustic charm. The Uruguyans I met seemed really friendly and the girls were quite pretty, but not up to the standards of Argentina or Brazil. I never got a chance to experience the nightlife but I met an English guy who was doing some college exchange programme for 4 months and he said the nightlife was excellent. Sorry I can't be more specific, but I'd say Montevideo's definitely worth checking out.
Punta Del Este / Montevideo, Uruguay
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