I live in Portland and spend a decent amount of time in wine country (both Willamette and Gorge).
Willamette has more non-wine things to do / variety, imo. I have my own list like all on this thread, but I'll mention a few personal recommendations. Carleton Wine Studio / 00 Wines (
https://www.winemakersstudio.com/) - One of my best friends is a MS for a distributor in TX and has OR in his rotation of producers to visit. 00 Chard is a legit as it gets in his book.
To kick start your trip off the plane in PDX, Amaterra (
https://amaterrawines.com/) is under a minute from our house and our daily driver. It's in the west hills overlooking the valley and just a great facility, great food and good wine.
If you do decide Willamette, I'd seriously recommend carving out a morning to hike Silver Falls / Trail of Ten Waterfalls near Salem (
https://www.wedreamoftravel.com/trail-of-ten-falls-silver-falls-state-park-oregon/). You'd be so close and it's a natural wonder. I can also give you some beta on a secret, Monk owned waterfall that you can couple with some Monk brewed beer

in the same area.
(It's Abiqua Falls / Mt. Angel Abbey brewery)