I was born and raised in Portland, but I have traveled all over the country, as well as other countries in the EU and Asia, and for a medium-sized city, there are few others like it in the U.S. If you can handle the gloomy weather, then portland is a nice spot to visit. I was reading an article someone wrote comparing portland to Seattle, saying that it pales in comparison---the writer stated that Portland is 1/10 the size of seattle, and there is nothing to do. Well, sure.. if you are a cynic... then Portland is not as big-it lacks some of the LA style night clubs, smog, traffic, and crime that you might find in larger cities. But if you appreciate good inexpensive food, micro-brews, wine tasting, quaint cafes, as well as friendly people with something interesting to say, then Portland might be the place for you. I'd recommend four days worth of sight seeing sometime in late spring to early summer, when the city is at its best.