And not as long as anticipated with our then, 28' sailboat. We always made it easily from CM to at least near the entrance to the canal, once the marina in the middle, and the reverse.
You should have an easy run up if the weather isn't too mean and you can go on the current.
We'd wait in Cape May for the proper weather but we enjoy it there, so an extra day or two was nice. The CM anchorage is pretty good, as is the the marina which we stayed for a couple days once. Jons right, I think we did graze a boat trying to dock in the wild current, and I recall the dock guys still thought we did pretty well.
There was a good seafood restaurant right on the water there years ago. The town is very nice, interesting architecturally.
I'm sure you'll love the Chesapeake. The weather should be perfect right now. Always seemed like quite a climate change to us when we entered the Chesapeake, even much later than now.