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Montevideo is a cool city but I didn't really find much in the way of nightlife. During the day it's a great city for walking around aimlessly. Montevideo is supposed to be one of the safest cities in the world but parts of it put me on edge - everyone seems to sit and stir so when you walk through non-touristy areas I felt watched. Lots of cool old European style architecture. Very provincial. I plan on going back within the next few years and getting a little more familiar with the area. MVD seems like it would be a great place to retire... just sitting around in nice weather, sipping Mate, strolling through the old town and the Rambla.
I'll second Colonia being worth a visit but it's easily done in a day.
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