OMG Yes .................................
Anyone ever sailed the BC gulf islands in the winter ?
................... as you'll see from the photos below. The winter one is taken somewhere miserable in the Gulf Islands of which I don't remember. The summer one is taken from a beach looking into Montague Harbour. Any confusion as to which is which

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Really, the only problem with winter in the Gulf Islands is that I'm getting a little soft . You'll definitely be alone whether in anchorages, marinas or tied to a B.C. Parks bouy. No drunken, screaming, all night parties. Unless you want to have one yourself and there's no one around to care. Locals are a little more anxious for company in the winter.
I'd recommend a central heater which has the equivalent output of a pig iron blast furnace to keep you warm and dry. Most marinas have power if you have electric heat. Also reservations aren't really needed at this time of year

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No doubt about it, the Gulf Islands are nice in the winter but would be even better if they were about 40-50 deg. warmer.