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Oregon for 6 days

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I am whisking my husband off to Oregon for his 60th b'day from Chicago.
After some research, here is what I came up with. I know it is ambitious, but we like to be on the go stay busy and wind down at dinner.
Day 1: arrive Portland by noon, spend time in the city- (dinner suggestions?)
Day 2: Cascade/Mt Hood area (suggestions as to where to stay)?
Day 3: Willamet wineries(big red cab and syrah fans --should I book a tour?) and spend a night Eugene
Day 4: Drive down the coast (which part is best on 101?)
Umpqua valley wineries --spend a night in Roseburg area
Day 5: Drive to Crater Lake, drive to Eugene for the night
Day 6: Nice breakfast in Eugene, then to Portland airport for afternoon flight.
Any comments, suggestions would be most appreciated!!

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