No surf till you get to VA. Beach which is not really accessible by sailboat....but you can take the boat into Norfolk and rent a car for your time there. Va Beach is honky tonk but fun for kids...nothing like Fire Island. Another alternative if you have time is to head
out of the Chesapeake and up the Delmarva Coast to Ocean City Md. which is an overnitght offshore
run. Finally there are the OuterBanks of N. Carolina which will take you 4-5 days of sailing/icw work and are fantanstic for eveything you want if you have the time. No offshore
or overnights required.
The alternative is to give up searching for Ocean Surf adventures and just enjoy the Bay. Annapolis
have plenty going on for kids...as does Norfolk. Or head
up the Potomac
to DC. Or just cruise
some of the smaller towns around the bay and pull into marinas
with swimming pools where the kids can chill.