I've been whale watching several times in Hawaii and a handful of times in New England. Whale Watching with Outer Island Expeditions in the San Juans was by far the best experience I've had to date. I had the pleasure of touring with Captain Beau, who I understand is the proprietor of the business, and is extremely knowledgeable about the area and the wildlife therein. He actually knew several of the Orcas by name and used his insight into the animals' behavior to position the boat for optimal viewing.
The boat ride was surprisingly stable, while we whisked through the water at about 30 or 40 knots. The quick transit allowed for a significant amount of time with the Orcas, and the opportunity to do some offshore viewing of some of the land-based wildlife on a few of the nearby islands. The small group size on the boat made for a very comfortable trip, with the opportunity to talk face to face with Beau about the surrounding wildlife rather than simply listen to a naturalist drone on over a loud speaker. I'm looking forward to booking another trip with Outer Island the next time I'm in the San Juans... I'm thinking about a fishing trip next time around assuming I can convince the wife to go along with such a plan.