Cruising
I do not recommend the trip between Nanaimo and Comox. Nothing much along the way. Instead if you can time your trip around July 1, it is a very nice sail (about 28 miles) from Nanaimo to Cocktail Cove (False Bay) on Lesqueti Island for your first leg. Normally, the friendly locals hold their annual Art Festival including a marching band that is a hoot to attend that weekend around July 1 (Canada Day). It is well worth the stop.
It is about a 34 mile leg to Lund from Cocktail Cove, which is the door step to Desolation Sound. During the summer months both of these legs have favorable winds and we regularly do both under sail all the way.
As far as the Whiskey Gulf restricted area goes, just monitor the weather channel on your VHF radio. The weather report provides up to date information on whether it is open or closed, usually a day or two in advance.
Where in Desolation Sound do you plan on visiting? I have some recommendations if you're interested. Walsh Cove (First Nation pictographs estimated at 3,000+ years). Also, in Degman Bay on Gabriola Island has several very nice First Nation petroglyphs that are several thousand years old.
Terry Cox