Lifestyle: Travel & Dining

Guide to Sag Harbor

By HRES Staff Writer - December 31, 2019

Sag Harbor, NY, is an excellent place for a day trip, a long weekend, or an extended vacation stay. Sag Harbor, a hamlet in the Hamptons, offers plenty to see and do. Sag Harbor is an old whaling town, and much of the architecture of that period remains. Sag Harbor offers a unique experience, and is fondly referred to as “The UnHampton.” The down to earth feeling and a distinct lack of glitz gives visitors an authentic taste of what the area was like before it found fame as the retreat for the rich and famous. 

For your stay, you will find a wide array of bed and breakfasts and small, quaint inns to choose from. Some have beach access to add to the ambiance of the experience. Sag Harbor is filled with local restaurants to satisfy any craving. Whether you want a world-class burger, fantastic fish tacos, or a fine dining experience at the American Hotel, Sag Harbor has it all. 

Sag Harbor is one of the most family-friendly places in the Hamptons. It offers a wealth of things to do with the kids in tow. Don’t miss the Wharf Shop, an old-school toy store, or the Sag Harbor Variety Store, which is a step back in time to the Five and Dime’s of a bygone era. When the kids tire of the beach, there are numerous beautiful parks around town for them to burn off any residual energy.

Sag Harbor is a place to spend time outdoors. Whether it is walking the downtown streets exploring the feel of an old fishing village, or spending time on the sand enjoying the beautiful beaches, this is the place to bring your best walking shoes. Give yourself a full day to explore the beautifully preserved architecture from the 18th and 19th centuries. The Greek revival homes of whaling captains will transport you back in time. The centuries-old Main Street is a relaxing place to stroll and explore the variety of shops. The harbor dock is a great place to take in water views and watch the sunset. 

The Hamptons have long been known for the vineyards that dot the countryside. Sag Harbor is no exception. While there, you won’t want to miss taking a tour and staying for a wine tasting at Wolffer Estate Vineyards in Sagaponack. They have a new “summer in a bottle” series, along with traditional offerings. 

Vintage shopping is a staple for those in the know about Sag Harbor. The downtown streets are lined with vintage and antique stores. Browsing through the stores, you can find vintage clothing and housewares, intermixed with works by local artisans. Many of the stores are housed in interesting buildings. Round out your shopping with a visit to the local Farmer’s Market where you can buy fresh produce, alongside freshly baked goodies and preserves. 

If watersports are your thing, then the summertime is when you will want to visit Sag Harbor. Wakesurfing, waterskiing, or taking a relaxing ride to Sunset Beach are all available from the harbor. You can charter a sailboat or rent a canoe to explore the inlets around Sag Harbor. Whatever way you prefer to be on the water, you can find it here. 

Sag Harbor also makes a great jumping-off point to explore the rest of the Hamptons. You can make the laid back vibe of Sag Harbor your home base while you explore the vast array of sites that the rest of the Hamptons offer. You will love returning the calming maritime tranquility of Sag Harbor after a day of exploring. 

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