Sag Harbor is different from the rest of Long Island’s highbrow East End. 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. In this post, we’ll delve into our visit there and tell you our favorite things to do in Sag Harbor.
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. This former whaling village and deep-water harbor keeps things low key and down-to-earth, relatively speaking.
Watch this video to get a glimpse:
Get Outdoors
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.
If you prefer to stay on land, you can explore the charming village of Sag Harbor, which is rich in history and culture. You can visit the Whaling Museum, the Custom House, and the Old Burying Ground, where you can learn about the maritime heritage of the area. You can also stroll along Main Street, where you can find quaint shops, art galleries, and restaurants.
Another option is to enjoy the natural beauty of the nearby parks and beaches. You can hike, bike, or horseback ride through the trails of Mashomack Preserve, a 2,100-acre nature reserve that covers one-third of Shelter Island. You can also relax on the sandy shores of Foster Memorial Beach, Long Beach, or Sagg Main Beach, where you can swim, surf, or sunbathe.
Eats + Drinks in Sag Harbor
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.
Watch this video for some more tips:
Where to stay in Sag Harbor
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.
Insider Tip
The Hampton Hopper is a new app that makes exploring the Hamptons without a car a whole lot easier. Shared rides between towns, or purchase a pass for unlimited rides all weekend.
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
Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributes travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She is fluent in Italian and Spanish and laughably adequate in French. Her background as an Early Childhood Educator gives her an added understanding of what it takes to travel with kids in tow. She firmly believes that the most important part of education takes place outside of the classroom, on the road, around the world. She never misses a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. Follow Allison at @gourmetrav.
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram