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From Main Street to Havens Beach: A Perfect Weekend in Sag Harbor

The Hamptons are the shining gem that defines the furthest tips of Long Island, with miles of both ocean and bay beaches and lush greenery that can be a rarity along the rest of the coast. The charming bayside town of Sag Harbor has walkable streets and plenty of charming stores and delicious restaurants for you to explore. Whether you’re planning on living in the Hamptons permanently or just for weekends, there’s so much to enjoy.
If you want to be able to vacation in the Hamptons whenever you want, an excellent means of doing so is buying or renting a vacation home. Sag Harbor’s central location makes it the perfect place to spend your weekend, no matter where in the Hamptons you stay.


One way Sag Harbor has maintained its historic charm from its days as a whaling port is the community’s fervent support of local, family-owned, and small businesses. From fashion and beauty to home furnishings and art, patrons invest in both quality goods and the local community.


From the chic, minimal luxury of Donna Karan’s Urban Zen to the uber-feminine LoveShackFancy flagship, Sag Harbor has outfitters for everyone. Check Joey Wolffer for luxurious jewelry and curated vintage, and Henry Lehr for your designer summer wear.
For men, fledgling local boutique Ryland Life carries a variety of brands from near and far, and even hosted a LOEWE pop-up in Summer ‘21. Also calling Main Street home are local brands like Leonard Frisbie and Sunswell, the latter of which we collaborated with for our ‘Beach Plum’ hats. (Make sure to get yours!)
For all genders and all ages, New York-based American heritage brand Faherty and an outpost of the local Flying Point Surf & Sport are your one-stop shops, while local variety stores like the 5 & 10 and The Wharf Shop are perfect for fun Sag Harbor swag and more!


You’ve pretty much made it as a town when you’re recommended in goop’s guides, and you’ve really made it when you get an actual goop flagship store, where you can find everything from curated beauty products to clothing and home furnishings. For the full spa treatment at another celebrity-owned outpost, visit Onda, which was co-founded by Noami Watts.

Home Goods

Nothing will make you feel more at home than beautiful homewares and furnishings, and Sag Harbor has plenty of shops frequented by top designers and design lovers alike.

For vintage and contemporary furnishings, Monc XIII is a one-stop shop. Bloom (25 Madison Street) features incredible vintage and antique pieces from around the world, as well as coveted white ceramics, and around the corner Sag Street Antiques is the perfect place to browse for treasures.
Sag Harbor Main Street is also home to many art galleries, coffee shops, toy stores, and more, to satisfy even the most discerning shopper.

Havens Beach

Havens Beach, Sag Harbor overlooks Sag Harbor Bay and is just a short walk from the streets of the downtown area. It may be a small public beach, but it still offers plenty to do. Not only can you partake in the typical beach activities, like swimming out to the swim dock, sunbathing, and tossing a beach ball around, but Havens Beach Sag Harbor also has boating and even a playground for kids. There is something for everyone in the family, and it’s in a convenient location. The downtown area of Sag Harbor is very much walkable. Whether you were to buy either a condo or townhouse in this area or simply stay in town for a weekend, you would be able to roll out of bed and walk right onto the beach.

Golf courses

There are few places in the northeast with better scenery for golfing than the Hamptons. Sag Harbor Golf Course is right next to Havens Beach and overlooks the bay. You can spend your summers golfing in a place where the greens contrast with the white of the beaches and the ocean's blue. If you purchase Sag Harbor real estate, you’ll have plenty of golf to play, as there is also the nearby Noyac Golf Course. Founded in 1963 and spanning 144 acres, this private golf course is great whether you want to play the entire 18-hole course — a par 72 — or just hit the driving range. The holes are distanced 7,007 yards from the tees, meaning you’ll have plenty of room to show off your new driver.
If you're really serious about golf, you might want to consider a membership at the nearby private Bridge Golf Course after buying one of the Hamptons homes for sale. This is one of the most expensive golf clubs in the country, but it is definitely of luxurious quality. This club offers incredible views, sits on 500 acres, and has furniture from 17th century France. It is the quintessential golf club expected to be in a place like the Hamptons, a lush location with a reputation for its high class. Whether you’re a serious golfer looking to join one of the most expensive clubs in the country or someone who just wants to casually try some golf out for the first time over a weekend away, there is plenty of golfing to do in the Hamptons.

Wineries and vineyards

What could go better with this seaside destination lined with mansions than a glass of wine? Luckily, there is plenty to try in the Hamptons, as there are local wineries and vineyards where you can sample flights of limited local wines. Channing Daughters Winery is constantly creating new lines of wine that you simply must try. Their 2020 Tocai Friulano is made from grapes from the Sylvanus Vineyard. It’s made from 78% Tocai Friulano and 22% Sauvignon Blanc to create a light, fruity flavor. It was a wine club exclusive through March of this year, so be sure to join to get sneak peeks of the newest flavors of wine.
There is also the Wolffer Estate Vineyard, which frequently holds wine tasting events. Join them for events like “More Than Meets The Eye,” where you will learn to sample wine with all five senses. They even offer non-alcoholic events and virtual wine tastings for people who still want to keep their social distance. There is enough flavor in these local vineyards to satisfy the palettes of buyers looking for Hampton homes for sale or visitors on a weekend trip.


Espresso Da Asporto has been a staple of Sag Harbor for over 20 years and is the best place around to get some to-go Italian cuisine. Take a break from lying on Havens Beach and walk over to Espresso for a soup and sandwich lunch. Have anything from Minestrone to Portobello Mushroom Soup, paired with a sandwich on focaccia bread, or come in for dinner where you can try a portion of any of their lengthy list of pastas. In addition, they have other delicacies like veal and eggplant, grilled New York strip steak, and several seafood offerings that fit the oceanside setting. Have calamari as a starter, followed by a dinner of flounder Milanese or salmon shitake as an entree. So whether you’re grabbing lunch on the go or want a delicious Italian dinner without the work, Espresso will be your new go-to.

Buying Hamptons homes for sale

Spend your vacation days lounging on Havens Beach and playing a round at the Sag Harbor Golf Course overlooking the water. Sample the selection of local wines and enjoy a great meal at Espresso Da Asporto. Buying Hamptons homes for sale either as a permanent residence or as a vacation home allows you to spend time and live life to its fullest, most luxurious, and most relaxing.
If you’re looking beyond a simple weekend retreat, and are ready to look into the process of buying one of the Hamptons homes for sale, contact a trusted and knowledgeable realtor like Mala Sander. Mala Sander+Team will be able to help you find your dream home in the Hamptons, where you can spend many beautiful vacations right by the beach. The inventory of Hamptons homes for sale is shallow and decreasing, meaning that you’re going to want a realtor to help you through buying one as soon as possible. The sooner you buy, the better chance you will get of owning your dream home.

Work With Us

We work with all kinds of clients helping put together the pieces of their unique puzzles, whether that means downsizing or upsizing, buying or selling, for everyone from Hamptons locals to household names from all walks of life.