Finding Old World Charm in Sag Harbor

It’s the quintessential small town. One that embraces its whaling history, while moving into the modern world in a quirky, eccentric way. Sag Harbor is like the hippie younger sister of the Hamptons and proud of it.


With a Main Street and adjacent alleyways chalk full of art galleries, restaurants and boutiques. It’s easy to spend an afternoon wandering in and out of all the storefronts and still not feel like you’ve managed to see everything.


Start exploring by walking down to the end of Main Street, stopping by the Visitors information, picking up The Sag Harbor Express, and finding a spot to take in the views while planning out a day of shopping, live music listening or plays and musicals at the Bay Street Theater.


Before leaving the harbor for shopping rent a kayak, take a boat tour, or rent a stand up paddleboard from Flying Surf boutique. Afterwards wander back along Main Street exploring all the nooks and crannies. Stop into Buddhaberry for a cool-down-treat before continuing on.


Take in the local historic architecture and if game visit the Sag Harbor Whaling Museum for some education on the local history.


On the way out of town stop by Bay Burgers for food and ice cream. Wednesdays are free ice cream day with the purchase of food.

Or hit up one of the local beaches such as Foster or Havens Morgan.