Oyster Bay, Huntington, Mystic, Sag Harbour (and environs), Block Island, Newport, and Cuttyhunk are all places I'd think about stopping.

When you get to Martha's Vineyard, you have several choices. I've only looked at Lake Tashmoo which is a bonifide huricane hole next to Vineyard Haven. My slightly less than 7'4" (or so) draft makes it problematic. Your boat would love it. With the great bus system on the Vineyard, it should be a treat to tour the island. If you were inclined, you can rent a car for a day in Vineyard Haven and tour the island. Edgartowne requires a mooring now. No anchoring inside, I believe. The south end of what used to be a great anchorage got blown out by a storm years ago. Look at Google Earth.

Nantucket is really neat -- but the billionaires displaced the millionaires and it's very expensive. But it's like Palm Beach (not so much jewlery and soft goods), but it's a special place. With your draft, you might not HAVE to take a mooring -- but if you can get one directly across from the Boat Basin, you can enjoy the view. The Boat Basin is like staying at good hotel (in terms of cost). But that marina is really classy. The moorings are the most expensive I've ever paid for. The launch is like taking a cab each time -- probably $6.00 each way PER person -- get the dingy out and use it ;^))).

Hyannis, plus some other places with your draft might be accessible. Watch that tide out there.

The distance from the western end to the eastern end would make some of the stops on the CT side a good idea.

I'm always amazed how much cooler it is as you get farther east.

If you would enjoy a day or so at the Mystic Museum, I'd really consider seeing if you tie-up at its marina. I visited it as a guest about the time you were last up there. As Larry said, I though it was very neat to be able to wander around the grounds without the crowds.

The bookstore and art gallery have both old and new pieces you might enjoy (and your wife can have her selections shipped ;^)))) -- she will have journeyed up there with you!

This is a shot of an area above that marina at the Mystic Museum. With you 5' draft, you should enjoy it.

Having said that, if you have time, Cape Cod with your draft could be fun, too.

Now I have to get the shovel ready. We're going to get 8-12" of freezing rain, sleet, then snow, the plumetting temperatures in the DC area over the next 20 hours. It started to rain already. :^(