Google brought up this article in the Vancouver Sun. Not just a race, more an exploration of the island and communities. Perfect way to spend a couple of weeks sailing.

There's another interesting race that just started in Alaska. Any boat human or sail powered(or both), any size, from point A to B along the coast. At first it sounded hokey but after looking at the 'course', a mixture of open water and inland waterway, I can't think what boat I would chose. Unlike open water sailing, races like this tax sailors abilities for long distance in little or no wind.

http://www.vancouversun.com/life/Isle+Yacht+Race+makes+waves/8570581/story.html#__federated=1