Sag Harbor is different from the rest of Long Island’s East End. This former whaling village and deep-water harbor cherishes its maritime roots and keeps things low key and down-to-earth, relatively speaking. Its inviting Main Street is packed with locally owned galleries, shops and eateries that remain open year-round. There’s even an art house movie theater for a rainy day diversion.
It’s surrounded by water so you’ll find plenty of aquatic diversions. You won’t find the crashing waves of the Atlantic, but bayside Haven’s Beach, with its soft sand, gentle surf and photogenic sunsets, is a treat. The bay water stays warm well into the fall, making Sag Harbor an ideal late summer or fall weekend getaway.
The calm waters are prefect for a carefree jaunt on an SUP or kayak. Global Boarding is located right in town and will provide all equipment and top-notch lessons. They run an alluring eco tour where a guide will help you discover local wildlife as you travel to peaceful areas accessible only by boat.
Eats + Drinks:
Vineyards on the East End are producing polished pours that are making waves in the wine industry. Leading the pack of artisanal Long Island producers is Wölffer Estate Vineyard in Sagaponack. The estate’s vivacious whites and balanced rosés are the sun-kissed essence of summer. Their latest venture is Wölffer Kitchen in Sag Harbor, the first winery-owned restaurant in the Hamptons. They feature wines from their estate as well as other top Long Island producers, served alongside a wine-centric menu of savory eats. Montauk tuna, ocean-to-plate stripped bass and briny nibbles from the raw bar are sure things. The house-made pasta and creamy risotto are irresistible. No reservations accepted for parties of less than six.
Baron’s Cove is a nautically inspired hotel with a breezy front porch, classic veranda and sweeping harbor views. Casually sophisticated, the 67 rooms offer private garden terraces, clean décor and loads of amenities. A heated saltwater pool, tennis court, fitness studio, bicycles, summer BBQs and lobster bakes and complimentary beach transportation make it the perfect in-town escape.
The Hampton Hopper is a new app that makes exploring the Hamptons without a car a whole lot easier. Shared rides between towns cost $12, or purchase a pass for unlimited rides all weekend for $35.
How to Get There: Ride the Hampton Jitney From Manhattan and you’ll be in the heart of Sag Harbor in two and one-half hours.
Photo credits: Global Boarding, Wolffer Kitchen and Baron’s Cove