Sag Harbor, located on the north end of the island, offers families downtown shopping and dining, as well as water access in the marina. Sag Harbor is home to dining, shopping and museums. For fun on the water, book a boat outing with American Beauty Harbor Cruises.

Enjoy lunch at The Golden Pear Café and then stop in the many stores and shops in the center of town.

Sag Harbor is also home to the Bay Street Theatre, where parents can enjoy a show on date night, and the Sag Harbor Whaling and Historical Museum, where families can learn about the history of whaling, which dates back to the 1700s. The beaches in Sag Harbor, like Foster Memorial and Havens, are also family-friendly with shallow, calm water in quiet environments.