East Coast US.
Best cruising, IMO, is Chesapeake Bay. You can spend an entire summer cruising this area, with something for everyone. Lovely museums, excursions to historic places, lovely coves, accessible to Annapolis, Washington DC, etc. Norfolk VA is tough to find a comfortable anchorage without a cruising guide, but interesting. This is an area rich in history easily accessible from the water. Read Michener's "Chesapeake", it's the most enjoyable of his books, IMO, nd gives you an idea of what the place is like.
New England. Maine is a beautiful but cold destination, with lovely coves, great fishing, lots of charm.
Rhode Island has Newport, Block Island. Lots more, but I'm hitting highlights.
Massachusetts. Boston, lots of history. Martha's Vineyard. Nantucket. Provincetown. Lots of places on Cape Cod. (you should read local pilots, some harbors are a bit difficult to get in or anchor).
Lots of places to explore in Long Island Sound.
Charleston, SC is a lovely, lovely city with a good maritime museum, friendly people.
Florida, the keys. And easy jump over to the Bahamas.
Since I'm a destination traveler, looking for things to see and experience, my tendency is to look for interesting land stops and gear our cruising stops to that.
I've never been to the West coast by boat, so cannot help there, but I've been told that there are not a lot of bays and anchorages compared to the East coast.