I started touring in the Seattle area. I lived in Bellingham. I rode back and forth between Seattle and B'ham a few times. I took two week-long tours in the San Juan Islands. You're going to have lots of great options. Also, my first "big" tour was down the coast, from Seattle to Santa Cruz, CA. It was awesome!

I would agree that touring while wearing a big backpack is a bad idea. Carrying it in a Bob sounds like a pretty good idea. You'd be able to take some nice hikes along the way.