The outer Cape is deserted this time of year, water is still warm relatively speaking, beaches empty, about 1/3 of the restrurants are open, along with shops.
Chatham KCQX is a fine airport with grass landing available. Clean diner with good food, at the airport above the FBO, big deck outside to watch the comings and goings while chowing.
Fuel is spendy, overnight in the grass tiedown was $12. Friendly spot with good eats. Easy routing with flight following if desired, simple to stay out of Class B Boston if that's your deal.

The islands just off the coast, Nantucket, Martha’s Vineyard and Block Island are great spots to visit as well.