Montevideo to me is a city of doors. I took a walk around the old town, and soon realized how intricately decorated the doors were, and each one of them seemed to be different from each other. If you have a chance to take a walk around the older section of the town, pay attention to the doors...
Montevideo has a lot of beautiful colonial buildings. Some of them are rather old (and badly in need of upgrades or maintenance). However, just the oldness itself is very beautiful. I'd rather prefer the prestine oldness that's real, than the updated and well kept newness that has lost the original touch of history. I spent a few hours one night wandering around snapping some pictures of old old colonial buildings... (It's worth doing but not recommended to be done alone on your own).
Juanico Winery about 20 minutes outside of Montevideo. I went there for a wedding. Unbelievable. That's all I can say.
Plaza Cagancha 1124 - 10100 Montevideo.. this is the address.
Nice little area of the bay where you have a nice view of the city. Here you can see people fishing.
People where getting pissed at the guy casting the net because that scares all the fishes away.
You may want to go and see some horse races at the Maroñas Racetrack. It has been recently refurbished and it's a nice experience. Ask at your hotel for the directions.
Towards the east end of town we ran into a wedding, I am not sure if you can tell from this picture but the bride appeared to be 7-8 months pregnant.