The American Hotel

Everything from the hotel’s restaurant to its eight rooms exudes Sag Harbors’ spirit of a fishing village turned hippie hangout.

Built in 1846 when most Sag Harbor residents were whalers, the stately American Hotel is one of the Hamptons’ most historic hotels. The brick building and white columned porch practically serves as a symbol for the town of Sag Harbor. Its downstairs bar has long been a hangout for the region’s famous residents and the restaurant, known for its gargantuan wine list, is one of the hardest to book. The restaurant serves upscale steakhouse fare with an expected Hamptons twist (think littleneck clams and caviar, for example). In warmer months, dining on the front porch makes for excellent people watching. A menu highlight, regardless of season: Maryland blue claw crab cakes.

Restaurant reservations are easier to come by if you’re actually staying in one of the hotel’s eight guest rooms. Each has its own individual décor scheme (one, for instance, features a mounted moose head) but all are large and vaguely Victorian with 19th century furniture and prints, Persian rugs and sitting rooms. Despite the semi-celebrity crowd in the downstairs rooms, the hotel atmosphere and service is not trendy but more of the New England B&B variety.