La Ciudad Vieja, or the Old City. This is the oldest part of Montevideo, once surrounded by walls. Since 1829 all that remains is the Puerta de la Ciudadela, the main gateway to this part of town.
The best way to get to know the Ciudad Vieja is to explore on your own then join a free walking tour. The young guides will give you loads of useful information about the area as well as tell you interesting anecdotes (did you know that Montevideo has a small Walk of Fame similar to the one in Los Angeles?).
The starting point would be the Puerta de la Ciudadela, which gives access to Sarandi, the main tourist boulevard. This is where most shops, cafes and restaurants are located and it is always very crowded.
As soon as you move away from it and venture into other alleys, you’ll find yourself surrounded by rundown buildings reminiscent of Cuban architecture. Dodgy characters sitting or walking around do not make the area particularly appealing so I wouldn’t recommend going there after sunset, but during the day it is fine.
Amongst the main sights that you will want to visit are: the Catedral Matriz (the cathedral), Teatro Solis, the Museo del Carnaval (the Carnival in Montevideo is similar to the Brasilian one but lasts longer!).
Lots of small and quirky art galleries and arts&crafts shops are another way to spend your time in the area.
Then when you are tired and hungry, head towards the harbour area: the Mercado del Puerto, an old and beautiful building that looks like an English train station, is where the main restaurants are. Eating here can be expensive but it’s definitely worth it: the meat barbecues are fantastic!