We grew up racing at Lewes YC. the racing is only casual during the summer season. I know about RBSA fairly well. I taught sailing there briefly and also, i org. a major laser regatta 04. I sail all over the chesapeake/delaware area in the laser and period. other classes. I pay as I go for sailing activities at Severn Sailing Association/Annap. and race during the winter season in the laser frostbiting series.
Eventhough, I have never cruised the del. bay and ches. i know alot about the weather patterns, conditions, waterways, boating/shipping traffic.
I have been on day cruising and training sessions on the chesa.nevermind, sailing in texas gulf coast.
I could speak intelligently about those aspects and certainly be helpful.
I can save you the details now, and tell you more about other experience, such as handling and piloting etc.
What sailing have you done in the area? And are you interested in sailing this winter?
Circumnavigating Delmarva is a grand sail to be undertaken! I read a well written account of a sail some years ago. This sailor went singlehanded.
Keep in touch, JRF