What size boat?
On the west coast of Oregon unless you are in a protected bay or harbor or in the Columbia, you pretty much are sailing in the Pacific ocean. With that in mind I would consider learning the basics in a class or on an experienced persons boat. If you were going to just get a boat and teach yourself, then I would start with something like a West Wight Potter 15 or 19 or a similar boat that is small enough to sail in a small harbor or trailer to a lake.
Once you cross the bar out of a harbor on the west coast you are in the big time on a lee shore and once the weather gets unpleasant you can''t always get back across the bar. For example the experienced charter captain that lost his boat his life and the lives of 11 passengers in Oregon this past fathers day.
You didnt say how much money you had to put into learning or buying, but if you are loaded, I suggest going to a sailing school and then chartering different boats to see what you like. There are a lot of schools and charter companies in or near the San Juans as well as the Carribean and most likely nearly everywhere else too.