Eastside Portland (east of the Willamette River)
One of my favorite things to do in Portland is to go get a beer and catch a $3 movie at McMenamin's Baghdad or Mission theaters. If you go to the Baghdad, you won't be far from a Stumptown Coffee Roasters - one the the highly lauded coffeeshops with outlets around the city and a country-wide following for their beans. And if you need some food with your coffee, Zell's is a wonderfully hidden brunch/lunch spot. Walking up and down Hawthorne St, Belmont St, and Division St will give you a good snapshot of Portland, with pricey little boutiques, dog-friendly bars, and the requisite ladies in Land-Rovers.  If you're so-inclined, there are quite a few decent places to take a vegan - The Farm Cafe is the best I've found.  After exhaustive pondering on the difference between hipsters and yuppies, try to make it to Rimsky-Korsakoffee for a pick-me-up: Rimsky's is an awesome coffeeshop with live music at nights, and secrets that I won't tell you about beforehand. If Rimsky's whets your appetite for the less money-ed, artsy, hipster scene where everyone has U-locks in their back pocket, you can then wander around NE Alberta st or SE Woodstock st. Alberta is part of old Portland, and is slowly being gentrified but fighting it. It also has the Tin Shed (one of my fav. breakfast places) and Bernie's (good fried chicken). You'll probably miss First Thursday and Last Thursday, which is when the galleries open and have wine tastings and when Alberta is taken over by hippies and artists selling their wares, but maybe another time.  On the way to Alberta, you may even drive by Toro Bravo, which is an incredible tapas bar.  After all this walking/driving, you'll want a beer and a bit of music, and the Goodfoot is perfect for that. It's a concert venue downstairs, and a pub/pool hall upstairs. They used to have breakdancing nights on Wednesdays, but you'd want to call to make sure. If you do make it to Woodstock, hit Ottos or the Delta Cafe, where I like to get a cucumber margerita and a catfish Po'Boy. However, since Alberta and Woodstock are basically the North and South border of what I consider the heart of Portland, it's possible you might not get to see everything. Go East out to 84th if you want asian food and such stuff - we recently got our first decent Malaysian restaurant out there. Then when you're about to pass out but need dessert first, one of Portland's newer dessert phenoms, Pix Patisserie has decently late hours.

Westside Portland (west of the Willamette River)
I love starting the day off with a solid breakfast, and my main love is Byway's Cafe. It's also within walking distance of Portland's main tourist draws: Powell's Bookstore. The downtown one is the only cool one to go to until you give up and start living in the suburbs and drive a minivan. Once you're finished being overwhelmed by all the books you have yet to read, walk down the street to Powell's Technical Bookstore, where you can get overwhelmed by more things you don't know.  Recover up a block to Pearl Bakery for the best bread in Portland. While you're in the Pearl District, you can swing by one of Portland's many breweries, and make a reservation at last years (maybe the year before) Restaurant of the year, Andina. (Only the fanciest places in Portland require reservations, but if you are inclined to plan ahead and have the $, I've included some favorites.) On Saturdays the waterfront along Naito Parkway comes alive with Portland's Saturday Market, 10am-5pm.

Burgerville - an entirely Pacific NW fast food chain that is our answer to In-N-Out, without the religion and with better fries and shakes and a seasonal, sustainable menu. Their fries taste like real potatoes.