It’s Portland, so you have to begin with coffee.
I’d go to Barista, and I’d get the single origin espresso. Barista has breakfast, but you could also go to the Waffle Window, and get chicken and waffles.
Then, take a walk around Mt. Tabor. It’s just a big park—well, actually, an old volcano. But to be honest, I guess it’s just a park that you can walk around and it's really nice.
After that, I’d take the Tri-Met downtown, and you can start day drinking. There are a lot of bars downtown, and just more foot traffic.
Barista Coffee's first shop in downtown's Pearl District is one of four locations today and a good place to start a walk through the unique neighborhood.
Mt. Tabor is a great spot to take a walk, set kids loose on a playground, or just enjoy the view.