Cisco Brewers

Since 1972 the Box has mixed Nantucket’s summer millionaires with its year-round working residents in exactly the democratic way only a proper dive bar can pull off. This is where the island stops performing and starts being itself.

The oyster selection here rotates daily with the tides, a serious raw bar on the working harbor of America’s most storied whaling town.

Outdoor tables directly on the sand are the most coveted reservation on the island every July and August, golden hour on Nantucket’s northwestern shore justifies every bit of the effort it takes to get one.

Jetties Beach is Nantucket’s most accessible, most family-friendly stretch of sand, and the Sandbar is the uncomplicated introduction every first-timer needs and every regular keeps coming back for.

The Vineyard’s best view from a barstool belongs to the Lookout, a democratic mix of seasonal visitors and year-round Oak Bluffs regulars that only a good tavern can pull off.