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Westport MA or CT? Yes it will be tight in either. You're likely to run aground.
In Response To: Westport Harbor ()

and in Westport MA if there's any swell running it might break your boat if you get put down hard in the harbor entrance. I'd avoid it with that draft -- there are some very nice alternatives in Buzzards Bay and also Cuttyhunk and Menemsha.

In Westport CT, lots of alternates very close that are deeper.

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