Circumnavigate the peninsula
We made this trip several years ago with 3-4 32 to 35' boats going north thru the C&D canal then joining up with our NJ friends behind the breakwater at Lewes,DE. We were off Ocean City with a storm starting up so all but one vessel stayed off shore thru the storm and went on off shore around the peninsula and thru the Chesapeake Bay Bridge Tunnel the next morning. Unless you have good local knowledge of the Ocean City inlet, I'd be prepared to stand off in bad weather and have enough crew aboard to run 24 hrs. The lightning in that storm was one of the most memorable and beautiful experiences in my 20+ years sailing, The slow hot doldrums comming up the southern end of the Chesapeake was not a high point of the trip, so if you go in mid-summer plan stops at marinas with swimming pools! Good Luck