FWIW, I lived in Bellingham, WA for three years (absolutely beautiful spot), and while sea kayaking around the islands was popular, I can't recall ever seeing or hearing of people exploring the area in a sailing dinghy or similar (absent a few who might putt around within a few 100 yards of shore). Not that it couldn't theoretically be done, I just didn't find that people did it, likely for the reasons already stated by a few folks.
Unfortunately, I did not spend too much time on the water there (the mountains were what had me there), but from the experience I did have, I can't imagine feeling comfortable navigating around those parts without a motor. But I'm kind of an over-prepared, over-thinking weenie too.
Lastly, if you do want to see what can go wrong, check out the episode "Swept Away" from the discovery show "I Shouldn't Be Alive"--which takes place in this area.
Discovery Channel :: I Shouldn't Be Alive :: Episode Guide