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Cuttyhunk is OK not sure of your age, me 33 so it's not a wild crowd, there are beaches and places to fish all around, there are also places to eat but be prepared to spend some dough if I remember right last year guy next to us paid something like $ 25.00 for a pizza. As far as the dog I have seen plenty of em on and off boats there. There are things to see and the views are nice, I am sure you can find some fish from the beach I wouldnt know always boat fish.
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