Re: first Sailboat and first sail from Annapolis to Washington NC
I am with Jeff and take some time to shake the boat down the first few days where you can get to a marinia should you find something wrong. Also make sure you get BoatUS unlimited Towing.
As James said having someone who has sailed and knows the southern Bay would be helpful and also increase your safety margin.
How far down the intercoastal do you have to go? How many bridges?