AS,
I sail in the Apostles on both my Beneteau First 36.7, but also my smaller First 235. Here are some random tips.
1) Mount your VHF antenna on your masthead. Do NOT relay on a handheld. I hear calls all the time that must be relayed by boats with higher antennas. VHF is line-of-sight, remember.
2) Wind direction is have a huge effect on wave size. Winds out of the NE there is 150+ of fetch in the North Channel and 6 footers can appear in almost any sustained breeze. Lots of lees, but watch out for the gaps as the waves come back fast.
3) FOG can roll in hard. Have a good GPS and a way to make lots of noise. The pump-style air horns work great.
4) Get as far north as you can. Do NOT launch your WWP in Ashland or Washburn. Nice places, but you will spend a full day getting to the islands.
5) Look for opportunies to dock in the islands and sleep on shore. More room. Unless you LIKE sleeping on board.
6) There is only maybe 3 anchorage in the AIs that offer true 3 sides protection. Mostly its 1 side +. Listen well to the forecast, and plan according. You'll see what others are doing. Best all-around is Quarry Bay on Stockton. Hard to get messed up there.
7) Docks fill up fast. Best if you have a small inflatable boat to get into shore if you have to anchor. Most anchorages have very nice sand bottoms on waters 10-20 feet. perfect.