Imba K.
Yelp
My first stop in Valpo. Cool, hip, trendy, mix of tourists, expats, and locals. Staff are young, hip, and friendly. Some English spoken, but use your Spanish if you can. The views out over Valpo and the harbor are amazing, and even if you are facing the "yellow house" on the terrace, its a great view.
Excellent wine list, beer and cocktails. Chilean beer is very unknown here in the states, unlike the wine, and I suggest you explore it in depth. I had a nice golden ale on tap, and a Chilean IPA in bottle that was richer and more complex than 90% of the IPAs I've had in the states.
Food is typical Chileno fare with a few twists. The machas (razor clams with parmesan) are great, and one of the shrimp dishes I had (came in a bubbling creamy stew) was crazy good. Fun to compare their shrimp to our Gulf shrimp here...very different, both excellent.