CBR - great trip! You have a lot of courage. That New england weather changes in a heartbeat. Currents, fog and rocks make the channel islands difficult. I take a summer vacation every year in Falmouth and always take a relaxing trip to the islands on my 160 footer. The Ferry has a great bar!
C Spray - Chesapeak Bay should be fine for you. When the wind blows out of the south east, the southern part of the bay can get pretty nasty. I am assuming you will be in the northern part. More to see & do. Bad conditions there are 3' to 5', spaced about 2' to 3' apart. That should be no problem for your 38" Formula. Let me know when you are coming through Annapolis - the Spring water is on me!