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14 days us plenty of time. Last time we did it in a week, but we had only one wind day.
We used Naturally Superior Adventures for our car shuttle and the vehicle was at the base on our arrival. We also stayed there on our last night.
After Aug 15 is risky as the west winds pick up then. June and July and early August are best. The old adage of figuring out one day in four will be a fog or wind day is good planning.
We found that getting on the water at sunrise and off by noon beat the worst of winds. I have heard of people paddling in the evening after dinner but Superior always continued its waves after dinner for us.
lets get you started
I advise that you be able to negotiate following seas to six feet without broaching. The west winds will bring up water waves that high even with a light breeze. Its not usually advisable to paddle right along the shore. Where there are cliffs there are reflecting waves which can easily upset you close in. Farther out a few hundred yards the effect is less. You might consider a drysuit and have rescue skills up to date.
Your food has to be in bearproof containers. You WILL see bears.