COLONIA DEL SACRAMENTO
A very small place, you can easily see the main sights (the tiny museums, the lighthouse) in a day. I stayed overnight at El Viajero which was fine – friendly and a good location.
http://www.elviajerocolonia.com/
It’s an expensive place. Nice jazz bar for drinks on main square.
ESTANCIA SAN PEDRO DE TIMOTE
Estancia magic. Just go. You will not regret it. I’ve been recommending this place to all and sundry. See my Trip Advisor review and blog entry.
http://www.sanpedrodetimote.com/
MONTEVIDEO
Where to stay
Palacio Hotel is a little gem. http://www.hotelpalacio.com.uy
Where to eat
The Mercado de le Puerte is a must. Try the medio y medio (half still, half sparkiling wine, a local speciality). I ate perched at the bar of La Chacra del Puerte – great fun, tasty swordfish and if you’re into meat, you can eat until your heart’s content (my companions did!).