Sag Harbor is a small, pretty town near the Hamptons. Although the location of some of the most expensive real estate in the country, this sea-side town prides itself on being outstandingly “unhamptons.” With an extensive whaling and literary history, Sag Harbor has distinctive appeal from the wealth and glamor often associated with the Hamptons. Popular with celebrities and devoted locals alike, this destination maintains a charming, vibrant atmosphere.

Adorned with Victorian manors, cottages, homes of early colonists, and Greek revival houses that belonged to wealthy whaling captains, Sag Harbor’s history remains intact among the addition of multi million dollar renovations and showier homes. Walk along Main Street and find boutiques, galleries, and exquisite dining options. Enjoy a sit down meal at 63 Page at Main for Sag Harbor’s specialty, oysters.

Sag Harbor is home to quirky traditions lacking in other Hampton sites. Celebrating its maritime history and place in Herman Melville’s classic Moby Dick, the town has hosted the Moby Dick Marathon every year since 1983. Over one weekend, different sections of the book are read in various locations around town.

Other highlights include beaches, golf courses, and wineries. Be amazed by the best of off-Broadway with a performance at Bay Street Theatre or kayak around the Clinton’s old stomping grounds at Georgica Pond. At night, bars and electric nightclubs come alive.