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shelter island is a good place to launch. I think that beach outside of shelter would be better as you don't have to deal with boats going in/out of that small opening.
shoot straight across to the other side and a bit to the right (towards the opening). there are rocks along there and tall markers in the water that mark alot of kelp. i would try dropping there along the kelp ridge or between the kelp and the rocks. the latter position will keep you a bit safer as boats don't often try to cross the kelp unless they are small boats going for lobsters. you can also fish along the kelp ridge to make time go by.
stay well lit. mark all buoys with lights. stay safe. stay warm.
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