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Seattle, Portland, and day trips all around

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Husband and I will fly into Seattle on Saturday, October 18. We will need to be back at a hotel in Seattle at least by Sunday, October 26 as I have a Seattle conference on 10/27 and 10/28 and will fly home on 10/29. We thought about returning to Seattle / couple of days sooner to explore Seattle? We are open to all suggestions, but here are our general ideas:

Maybe head straight to Portland and stay for 2-3 nights doing day trips to Mt. Hood, the Columbia River Gorge, and Cannon Beach?
Mt. Rainer?
Mt. St. Helens?
Olympic National Park?
Ferry ride?
Whale watching trip?
San Juan islands?

Our favorite activities include hiking, eating, drinking (beer and/or wine), kayaking, farmers markets, people watching, etc. We aren't really museum people--more into experiencing nature and local culture.

Not sure what the weather will be and how much we can fit in and still feel like we have some freedom to stop and enjoy the beauty. In addition to structuring the trip I would love recommendations of places to stay and eat, etc.

Thank you in advance!

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