Sounds like a fun trip you have planned. My top recommendation for a trip that has all of the above (out of the way pretty wineries, good food, interesting accommodations and a close flight) would be for you to focus your trip on the southern portion of the Willamette Valley. The entire Willamette Valley is more than 100 miles long, with wonderful wineries throughout. I don't know how long your trip will be, but if you don't want to spend your entire trip driving, I'd...
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