Martha’s Vineyard residents seem pressed to compete with the nearby island of Nantucket, which is less than half the size but has arguably more cachet. Whereas Nantucket is generally flat, they’ll tell you, Martha’s Vineyard boasts dramatic sea cliffs at Aquinnah on the far southwestern corner. Locals also take pride in the fact that the northeastern town of Oak Bluffs became a prestigious vacation destination for Black Americans as early as the 1930s. Oak Bluffs maintains strong connections to that history to this day, hosting the long-running Martha’s Vineyard African-American Film Festival, for example.

On the island’s far eastern side, Edgartown was a stop on the Underground Railroad. But it’s perhaps more famous for its many well-preserved 18th- and 19th-century buildings, including numerous grand mansions constructed during the town’s whaling era. The architecturally harmonious center is a pleasure to explore on foot or by bike, pausing at whatever boutiques, galleries or restaurants strike one’s fancy.

Faraway Martha’s Vineyard

Right in the heart of things is the new Faraway Martha’s Vineyard, occupying the refurbished and rethought Kelley House, a hotel that once housed the cast and crew of the film “Jaws.” Its 58 accommodations are divided among the original buildings (the oldest dates from 1742) and neighboring cedar-shingled homes converted into rooms and suites. We checked in only a few months after it opened in June 2023 and discovered a self-consciously stylish property as Instagram-ready as could be. But ready for discerning travelers it was not.