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There eventually comes a point where any boat is too small, if the conditions get bad enough. The bigger the boat, the less often that occurs.

That said, we routinely fish and cruise the same waters in an Outrage 18/19 hull (18.5'). No, we are not out there during winter. But April-October, even March & November weather permitting, the boat can handle ordinary Bay conditions.

You'll want to keep tabs on weather, and consider heading to more protected waters if a Small Craft Advisory is forecast. But as long as conditions are moderate, you can criss cross the Bay in that boat to your hearts content.

Good luck and let us know what you decide.