Mike,
I think weather and your tolerance for seas will dictate when and where you go.
Buzzard bay always seems to get worse as the day progresses, but its only a 7mi ride from the southcoast ramps to the elizabeths.
I've been from falmouth to Oaks Bluff in a leaky 14ft smokercraft, but with one guy on bail duty and one on the tiller we got to get expand the areas we've been skunked.
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What areas do I want to avoid with a boat?
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As long as you're motor is sound, you've got fuel and the seas are calm, go anywhere.