Re: Norfolk, VA to Boston delivery
If you do decide to go outside and it gets snotty remember deep water is your friend.
I would be VERY reluctant to run an unfamiliar inlet. If you feel you HAVE TO then there is no shame in asking for someone to pilot you in. I remember well having to enter at Cape Fear and although it was buoyed and one of the easier inlets I was VERY glad that I called up a passing shrimper and he slowed down to let me follow him in. [ and he threw a lb of shrimp into my cockpit. Me and the cat were well fed before I slept that night.
If in doubt stay out. Too many boats and lives have been lost trying to run an inlet in less than optimum conditions.