If you like bars and drinking, Portland has some of the best dive bars out there. When I have friends from out of town I pick a neighborhood, start in mid afternoon, and just play the one drink per bar game. Only 1 drink, no matter what....... well maybe two, but that's it, any more and you start to become part of that bar. Keep it to one or two and you are always new and fresh, you don't get to drunk, and your very social. Doing this is a good way to see the downtown area and stop at a few food carts while your out. A few of my favorite places for this are
1) Downtown, 3rd and Ash street area, heading towards china town. Make sure to hit up Shanghai Tunnel, Ashstreet Saloon, Dantes, Bar XV and a few strip clubs Marys and Magic Garden in this area.
2) NW 21st/23rd area and Burnside towards the city. The Marathon and the bars around it on burnside are great hangouts, Blue Moon, Silver Dollar Pizza and others are good here.
3) Hawthorn area, don't know this well enough to give specific advice but another great neighborhood.
