Can't thank the folks at Desolatation Sound Yacht Charter enough, they are the closest sailboat charter to Desolation Sound. Their chart briefing alone is worth it.
Getting there is a little hard. Either take Kenmore Air up to Campbell River and then Sky High Shuttle down, but seems a waste. Too bad Campbell River doesn't have a yacht charter. You can also charter a seaplane to Comox direclty, but that is expensive. In the end, the cheapest way might be seaplane to Victoria and then rent a car up there.
In terms of places to go, the Tuba Wildnest Resort is amazing. What an incredible view. And in terms of staying, the Seattle Yacht Club has a terrific outstation on Cortes Island and the Cove Restaurant in Squirrel Cove is delicious.
Don't forget to get the Canadian plan with AT&T if you go and avoid that ridiculous data plan charge of $1/MB by getting a Rogers SIM for data if you can.