Welcome to Oak Bluffs, the most exclusive Black beach community in the country. Known for its gingerbread Victorian-style houses and modern architectural marvels, this picturesque town hugging the sea is a mecca for the crème de la crème of Black society—where Michelle and Barack Obama vacation and Meghan Markle has shopped for a house for her mom. Black people have lived in this pretty slip of the Vineyard since the 1600s and began buying property in the 1800s, making this posh town the embodiment of “old money.”