Martha's Vineyard and Boston Eats?

The wife and I will be traveling to Martha’s Vineyard and Boston for a week. We enjoy spots where the locals go for casual food and good drinks. The first three days we will be in Martha’s Vineyard and plan on eating at Red Cat Kitchen and Nancys for lunch or dinner. We do plan on doing a day in Nantucket if any places you recommend would be greatly appreciated. While in Boston we staying at the W and the only place we have set in stone is Legal Seafood. We would like a night of good Italian food in North Boston and open for there on out.