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Oregon 2 Week Circle Tour or Longer

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We are planning a circle tour of your great state in Late August, early September 2012.
Being from Florida and in our 70's, are not interested in hiking, too much beach, though the Oregon Coast is much different than our beaches.
Here is our Basic plan, subject to change, depending on the advice from you Fodorites.
Fly to Portland. Rent a car at the airport, Stay 3 days in Portland. considering side trip up to Mt Helena. The on to the Gorge area as far as Hood River or the Dalles via Interstate or historic Highway? . Then south to (Hopefully) TimberlakeLodge for a day or two, then on down to Bend, Crater Lake Area for 2 days, to include Rogue River Boats then on down to Crescent City to see the Redwood NP 2 days? Back up Coast to perhaps Florence, Yachats? 2 days, The to up to Tillamook, to see cheese factory and go to see Spruce Goose in McMinville, on to Wilmette Wine country (probably another 2 days)and back to Portland to fly home. Most confused on where to stay on the Oregon coast . More interested in History of Coast, such as Lighthouses, great quaint, scenic lodging & great seafood. Will there be any fruit available at that time of year?

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