Gardyloo - thanks for the suggestion for the coastal route, pictures are great!

here4now - thanks for the feedback on Newport. That is not the image of the coastal town I'm looking for so I'll keep doing some research on the other locations. I appreciate your feedback on your experience.

Tomfuller - fort clatsop was not on my radar yet so I'll add it to the list of things to research. I will look into Yachats as well (thanks for the providing the correct pronunciation, I would never had got that!)

If you're looking for cushy adventures with nice restaurants and accommodations then Bend and Hood River should be at the top of your list. They are both different from Boulder.

If you want a little more off-the-beaten-path adventure, then go to Crater Lake first and then drive Highway 199 (the Redwood Highway) to the Oregon Coast. The South Coast is beautiful and there are tons of wild rivers to hike around and explore. If you want to see a dramatic and rugged landscape, find a way into the Kalmiopsis Wilderness. You can drive back up the coast to Portland to make a nice loop out of it.

I also really like the Elizabeth Street Inn. The beach is beautiful and is also close to the Nye beach area which has quite a few restaurants.