I like Valparaíso, an hour and half from Santiago, V Region, cos' is a magical place, the hills, the sea and the elevators makes him completely original.
I love his streets and old buildings, remembers of an english legacy, with the port and the navy culture in the city. I think I really enjoy Valparaíso - a mix of Valle & Paraíso (Valley and Paradise)-, because I'm a history lover and all the little details about the people, the stores, the fair with amazings antique, the old restaurantes, the musicians in every corner, makes me feel participant in a pretty story.
My favourites hill are Cerro Alegre and Concepción, the first one because had a wonderful houses and buildings adapted to the geography and the last one, Concepcion's Hill had a pretty coffees and seafronts with a view to all the ships and cruises at the port.
The first time I was to there was in the year 2005, but I'm not pretty sure... I went with my mom and my sister a weekend and we stayed in a residential of a germany woman at Plaza Sotomayor. That time we visited all the important hills of the city walking from de beggining to the top: Such a hard crossing!! But was the funniest quick-travel in my life! Since there I looooove Valpo. and the last time I visited was 2009, I guess.. in New Years Eve.