Originally Posted by chef2sail
We have done the circumnavigation route a couple of times. You should note that the only really passable inlet from Cape May/ Lewis to the entrance to the Chesapeake at Norfolk is Ocean City Maryland. snip
Correction: My recollection below was flawed. My club didn't go in a Wachapreage, they went in at Chincoteteague. I think Wachapreage would be doable, but don't know anyone that's done it in a sailboat. I do have a friend that has a big fishing boat he keeps there.
I hear that statement often, but when our club did it they went in a Wachapreage with no problem. I'm not sure the sizes of all the boats that participated, but the lead boat was a Valiant 42 and I think the rest were in that size range, or slightly less, so we're not talking about little boats.
Probably better done with local knowledge or lots of advanced planning, but it can be done. There is a Coast Guard station there so you can probably ask for some guidance from them if needed. There are lots of large fishing boats including large commerical fishing vessels with drafts equal to a midsized sailboat that use that inlet routinely.