The New England coast has a lot to offer...especially after dealing with Long Island Sound and New Jersey's coast.
There's Newport and Block Island in Rhode Island.
Then there is the beauty of Buzzards Bay, the Elizabeth Islands, Martha's Vineyard, Nantucket and Cape Cod, with many good destinations like Hadley Harbor, Cuttyhunk, Tarpaulin Cove, Menemsha, and more.
Cutting through the Cape Cod Canal, which can be very interesting to try and transit with a southwest wind... brings you to Massachusetts Bay and Boston Harbor. Boston's outer harbor has about a dozen islands to explore.
Heading north, you'll come up to Marblehead, Great Misery Island and then Gloucester, on the southern side of Cape Ann, Massachusetts's often overlooked Cape.
Rounding Cape Ann you'll come to Rockport, with Motif #1, version 2., which may be one of the most popular subjects of painters and photographers. Be aware, there's a big sea break northeast of Rockport Harbor, and you need to go AROUND the buoys, not between them.
Then you head up in to the Gulf of Maine and Casco Bay, which is beautiful, but can be somewhat unforgiving, given the dense fog, dense swath of lobster pot buoys, and rocky coastline.
Hope that helps.
You could spend years exploring New England and all it has to offer, and the winds here are far better than the flaky, fluky winds you'll find on the Chesapeake.
We also have far better seafood than anywhere else in the world.