In Valparaiso the hills or the Cerros are the best places to stay as thats where all the locals live and besides, downtown 'el plan' has a dodgy reputation at night. If you are looking for somewhere to stay I can recommend Allegretto Bed and Breakfast on Cerro Conception. With very friendly and helpful english speaking owners it makes a great base for exploreing Valpo. They also have a dorm room for those on more of a budget and the price includes a hearty breakfast. About £10 a night for the dorm and £30 for a double room and bathroom. Inside it has a homely feel with a big airy communal area and restored wooden beams and floorboards as well as a well speced kitchen.
Valparaiso itself has a spectacular setting, its basically just a set of big hills coming out of the sea with a brightly coloured city clinging to the sides. In the distance you can see the snow capped Andes. You can just see mt Aconcagua at 7000 meters the highest in S america in the distance, which is in Argentina. A lot of the town is decaying and decrepid -compared to how it once must have been in its wealthy heyday- but is full of hustle and bustle and after the initial culture shock it has a charm that sort of creeps up on you. - and a seemingly endless selection of fantasticaly dingy bars and clubs that are open all night....
The owner also runs tours of the historic bars and is a great source of local information. His restaurant just down the road also serves a tasty pizza. Recommended.
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