The main spots of interest to expats are (west to east):
Colonia del Sacramento: laid-back town with a World Heritage Site. This is where the Argentine hordes pour onto and off of the boat from Buenos Aires before driving at reckless speed to Punta del Este to join the glitterati.
Montevideo: city of 1-1.5 million people, either charming or filthy, depending on how you look at cities in general.
Atlántida: 30-40 km east of Montevideo, mostly charming beach town beyond the considerably less-charming Costa del Oro. Population swells in the summer, but it the town doesn't die in the winter, and from there to Punta del Este it's the only one about which that can be said.
Piriópolis: a little closer to Punta than Atlántida is to MVD, this resort town is something you simply have to visit to see if it resonates with you.
Punta del Este is actually the tip of the peninsula, but so powerful is its aura of glitz and money that all the Maldonado highrises call themselves Punta. While becoming considerably less dead in the winter the last few years, it remains a showplace for hard bodies, fast cars and yachts in the summer. Some people think that's awesome; others avoid it like the plague between mid-December and mid-March.
Beyond Punta, to the Brazilian border, beach towns that may or may not be interesting as a place to live: über-expensive Jose Ignacio, Paloma, La Pedrera, Cabo Polonia, Punta del Diablo and others.
