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Seattle Suggestions?

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My husband and I will be visiting friends in Seattle (Greenlake) this October. We will be visiting them for a weekend and then staying for a week on our own to explore the city and surrounding area. We are very excited b/c we have never been before. Our friends have not had too many suggestions on what to do or where to stay really so I am hoping I can get some advice.
I think we'd like to stay downtown Seattle during the week as a base camp. Any suggestions on hotels?
We'd also like to go to Mt Rainer for some "light" hiking. Do we need to stay overnight there or can we just make a day of it and return to the city.
Wineries?
We are also thinking of checking out Portland for a day but not sure if this is realistic ? Too much driving?
I have heard about the San Juan Islands? Worth checking out?
We love food (some vegetarian) so restaruant suggestions would be great!
Any advice is much appreciated!

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