Ryan, the Barber's Pole side of Cow Island is going to be a lot calmer than the other side. The broadside of Rattlesnake is going to be a lot rougher than the west side. Between Treasure and Sleeper's is going to be calmer. If you can get in a smaller area without the wide expanse of water, it is going to be calmer. I agree with Pricestavern that the Northwest wind is the most common.
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