Reddit reviews Canoe and Kayak Routes of Northwest Oregon and Southwest Washington: Including Southwest Washington
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Used Book in Good Condition
Ross Island is the obvious close one.
Columbia Slough is hit or miss--it's very dirty in some places.
Smith and Bybee is great right now--you can probably still catch the nesting osprey.
Scappoose Bay is especially fun when the water is high, because you can kayak through the forest. I haven't gone this year yet.
Multnomah Channel is fun if you like goat cheese fritters at Marks On The Channel, which I highly recommend.
There are lovely sections of the Tualatin River, but stay away from the part that goes by Lake O because the current is dangerous.
Is Elk Island still an island right now or is the water too low? If it's still an island then that means it is likely hobo-free and makes for a good picnic spot.
There are literally over 100 boater-only campgrounds on the Willamette between here and Eugene. One of the best vacations of my life was floating from Eugene to Independence and camping along the way--for free. You don't even have to pack much food because nearly every river town has a store within walking distance.
I recently did Luckiamute but I would not recommend that place until you get a little more experience.
If you're looking for an easy overnight, I like Wells Island--especially if you have a fishing permit.
Nehalem Bay is pretty rad. Check the tide tables before you go, so you can float from Wheeler to Nehalem for lunch with the tide, then back to Wheeler as the tide goes out.
I have a few books that include many fun routes in the area. I think this is one of them.
If you're looking for a whole week trip, shuttling down to Corvallis and paddling the Willamette back up to the pullout in West Linn is a good 5-day expedition. I did it with the Boy Scouts one summer, and except for the one day of unseasonally torrential rain we had a great time. The Willamette River Keepers has a pretty detailed "water trail" map of the river with marked camping locations and points of interest.
I don't know if they're the best books on the topic, but I have these two:
Soggy Sneakers has more whitewater stuff in it, but both have a good number of flatwater trips as well.