If you ever happen to be in Martha's Vineyard, I love Menemsha in Chilmark, it's where Jaws was filmed, you will recognize it immediately. And for food go to The Bite, it's insanely expensive and supposedly delicious. I have never eaten there because I am allergic to shellfish but apparently it's ridic. Second rec would be to check out the campgrounds right off of the main drag in Oak Bluffs, they are pastel tiny cottages that were built in the 1860's. My daughter is convinced that they are where all the witches live and this may or may not have originally been my sister Paige's influence. And another would be breakfast at Art Cliff diner, the wait is forever so don't go "hangry" in other words angry/hungry.
xoxo, The Little Bean Crew