Montevideo sits right on the water, with several boardwalks, 'ramblas', that border the beach on the Southern end of the city. The city has many beautiful parks, the most popular being 'el Parque Rodo'. There are a couple of major markets, two of the most famous being 'la feria de Tristan Narvaja' and 'Biarritz' where you can find everything from fresh produce to antiques and everything in between. Pick up a freshly grilled 'chorizo' or 'morcilla' to munch on while you walk the stalls, and don't forget to get some 'churros' for dessert.
'El mercado de los artesanos', is an arts and crafts collaborative that sells wonderful local work in leather, silver, wool, and other typical materials. In the old city, there are wonderful antique shops to visit, and some great theaters as well. If you happen to visit in February/March, Montevideo has a fantastic Carnaval. Distinguishing it from versions in Brazil and Argentina are 'Murgas', street theater with singers and drummers that precede Carnival season.
Although practically surrounded by water, Uruguayans are die hard carnivores, and Montevideo is no exception. Be sure to make a pilgrimage to the market by the docks, 'el mercado del puerto', for a genuine Uruguayan 'parrillada'. 'Chivitos' and 'milanesas' are other delicious staples, and for the more adventurous palate, all the other parts of the cow can be sampled as well.
Montevideo is a strange combination of Spanish and British influences from over the years, but its true wealth lies in the extremely rich architectural heritage and the sheer number of artists, writers, and musicians who have made their home here over the years. Montevideo is also a major center for education, with close to a dozen universities scattered throughout the city, and although it is a modern city rivaling any other with plenty of skyscrapers and gritty sections, there is more than meets the eye, although it's certainly true that seeing beneath the grimy exterior takes a little bit of effort. However, once you begin experiencing the true cultural flair of the people themselves, you will find Montevideo beginning to grow on you. From dancing the tango to heading out to one of the beaches or strolling through one of the sprawling parks or walking through the historical sections of the city and taking in the Spanish colonial architecture, you will continually find yourself wondering if you really ever need to leave.