I fish the Delaware Bay out of the Roosevelt Inlet in Lewes, DE. Yes it can get choppy if the wind picks up and is against the current. But most of my trips have been nice. I now have a Helms 25 now and plan to sail the bay many times this season. Take a look at the chart of the bay. There is a lot of deep water for great sailing. I would say the river section to where the bay opens up is you biggest concern with shoals, current, ship traffic etc.. Like anywhere else, plan your trip. Take a look at current, tide and wind. A stop over at Lewes might be a nice addition to your trip depending on the time you have. Its a nice town. You'll have to cross the bay to get to Cape May though, but a great 18 mile sail. At least your starting to plan your trip.