"One large city and then wide open spaces" Uruguay by melosh

After Montevideo and the built up coastal resort areas, Uruguay is characterized by the wideopen Pampas where the cattle and sheep outnumber the humans. Unlike some of the very flat plains near the coast and seen in Argentina it seems a large part consists of an undulating surface. As one native said, God forgot to iron Uruguay.
The small towns in the countryside, with the possible exception of Colonia (which as a river port city does not really seem to be in the countryside), have very little to attract tourists beyond a quieter daily life than Montevideo. As one might expect, the people are even nicer than found in Montevideo.

Guaucho wear used at Estancia Canada

After driving or busing through the open countryside, I think you really have to stop at an estancia or two in order to connect with the history and culture of Uruguayan farm/ranch life. Through the internet or by means of a visit to a national tourist information office you can get a long list of estancias, rural hotels and resorts. The problem is that often the tariffs are not indicated and I found making reservations could be a challenge. The national offices will not help you with booking.
There are at least two "coffee table type books" of beautiful pictures of historic estancias in print but these are not really guide books.
It is very important that you do as much research as possible so you will have realistic expectations. Do you want a place that is trying to be a resort with perhaps a swimming pool etc., or a place that prefers to remain true to its rustic past?

Punta del Este

The most visited attractions outside of Montevideo are Colonia de Sacramento and the eastern beaches that range from the internationally famous Punta de Este to quieter, less developed coastal towns.

Colonia is tranquil and has lots of preserved historic building from its Portuguese and Spanish past. The large flow of visitors supports an extensive array of romantic looking restaurants and hotels.

I was told that the sunny warm beach season is really limited to late December through February. When I visited in November no one was in the water or even sunning themselves on the beach. It was sunny but the water is very cold and there was a strong wind.

• Pros:Educated, cultured, relaxed people with a history
• Cons:No good guidebooks
• In a nutshell:More than just Montevideo, Punta del Este and Colonia