Portland proper is not a big town. Most of what you want to see you could realistically be done on foot. However it's also an easy place to drive.
People are friendly, coffee and food are great. Go to Lardo (killer sandwiches), Stumptown (great coffee) and Voodoo Donuts (don't be deterred by the lineups). I was in Portland for four days before I saw a McDonald's.
Wine country is great and a short 45 - 60 minute drive from downtown.
We had two types of weather during our stay. Raining or feels like it's going to rain. But the temps were moderate. 15C and grey every day.
The best comparison I can make to the choice in Portland for local beer is Netflix. You can spend the bulk of your time trying to decide what to drink. Most accounts I received were that there were 50 - 70 breweries in Portland and around 100 in the state. Choice can be a bit of a painful thing in a beer town like Portland. Multiple IPA's (5-6) were not uncommon at any particular brewery.
Also the bottle selection at the Whole Foods is incredible. I'm sure there is a reason (state law, travel time, Crown Corp control here) but many of the Belgian beers we have been lucky enough to get here (Saison DuPont, Lindemans, Oud Beersel) are all considerably more expensive in Portland even before the exchange.
Places I went:
Deschutes Public House - Great location in the Pearl District. Good food, good atmosphere and beer. The Deschutes freshly squeezed IPA was excellent. I bought a six pack at Target around the corner. That store had way more brands of IPA than BML.
Rogue - Bought a bottle of Dead Guy Ale at the Farmers Market. It was underwhelming but a good example of the style that some might call out of place in a hop crazy town.
Upright Brewing - Excellent American takes on classic Saisons. The tap room is the actual brewery. Nice folks and lots of interesting beers. One disappoint was a still beer that was made in conjunction with a local winery. Brought back a bottle of August IPA. Made for the rare beer club in Portland.
Commons Brewing - One of the most talked about new breweries in Portland. I didn't get much time here as there were no minors allowed on premise. It's a must if you make it to Portland. Excellent examples of classic Saisons and Witbiers.
Cascade Brewing Barrel House - Amazing sour beer. Lots of fresh hop incarnations when I was there as well. If you have limited time in Portland put this place on the top of your list. Brought back a bottle of Framblanc. White Raspberry sour from 2015.
Culmination Brewing - Another new brewery in Portland. Great pale ales and IPA's as well as decent food. There is a cider house right next door as well.
10 Barrel Brewing - Now owned by InBev. However the consensus with a couple of people I spoke to at Lardo is that it hasn't change at all. I had a fantastic Simcoe SMaSH there. Again had I had more time I would have filled my belly to my neck with that one.
Fatheads - Great IPA (Built for speed). Dry, grainy and perfectly hop balanced. Not my favorite local but the beer was top quality. My wife had the Kolsch which was an excellent example and close to one I've brewed.
Last but not least:
de Garde Brewing in Tillamook, Oregon.
We rented a car and drove to the coast. Which happened to be near the most talked about brewery in Oregon these days. Set in the valley between the ocean and Tillamook forest in an industrial park. Don't let the location fool you. The spontaneous fermentation and barrel program there is world class. They are even lucky/good enough to have rotating tap of Cantillon. Again I didn't have near enough time to enjoy but it stuck out as my favorite. It's a bit of a drive to get there but worth the trip. The drive down there is also quite nice as well. Bottle of wild farmhouse saison and a bottle of wild red ale aged in oak with cherries and raspberries.
Again there was so much choice in Portland. Portland has drinking local down. So did the great beer scene come out of the community wanting great local product or did the great beer provide the want. My guess is that it's a bit of both but who cares. If you want a great beer getaway go to Portland, Oregon.