Exploring the Hamptons, the Exclusive Retreat of Long Island’s East End

Lavish estates, gorgeous beaches, glamorous galas, high-end retail, upscale dining, and invitation-only events. Welcome to the Hamptons, the exclusive retreat of Long Island’s East End. 

The Hamptons’ reputation for luxury dates back to the late 1800s when wealthy New Yorkers began building mansions and summer homes as a retreat from the city

In 1893, the New York Times described the Hamptons as “Exclusive—in the best sense of the word—society is here represented during the summer by its choicest spirits. Well-bred men and women find a congenial atmosphere, refined attractions in plenty, and innumerable charms about these quaint old villages.”

Meet Vanessa Gordon. A thirty-year resident of the Hamptons with a family lineage spanning over a century on the East End.

In the early ’90s, when I was very young, the Hamptons recently went through a business and commercial/residential real estate boom during the mid-eighties. That time was a significant turning point for the wealthy moving out and building their summer residences in the Hamptons,” Vanessa recalls. 

The Hamptons have experienced significant changes over the years, with the once-sleepy beach community now transformed into a hub of activity, drawing high-profile visitors from all over the world.

“Besides the village of Sag Harbor, which has consistently maintained its integrity and charm, the epicenters of East Hampton, Bridgehampton, and Southampton, for instance, are now predominantly populated with main streets that perhaps resemble the Upper East Side or the West Village with top designer shops in the fashion, interior design, and beauty industries,” Vanessa explains.

Beyond Luxury: The Hardworking Community that Sustains the Hamptons

Despite its reputation as a playground for the rich and famous, the Hamptons are also home to a tight-knit community of year-round residents who work hard to sustain the area’s unique charm and character. 

“There is a significant blend of new families who have recently made the Hamptons their full-time home and those who have lived here for 15-20 years or more. The locals, in particular, are incredibly hardworking, hands-on, and proactive in the community. The lifestyle is a mix of the trendiness of the city meets a suburban seaside community that is still very rich in history and culture,” says Vanessa.

Vanessa’s contributions to the area are indicative of the hardworking nature of the Hamptons community, a place where hard work and community values are still highly prized.

She founded the Hamptons Interactive Brunch in 2018, one of the headlining annual summer events that partners with local non-profits each year. She also regularly serves on the committee for different fundraisers and galas. 

One of her most recent endeavors was serving as Junior Co-Chair during the Stony Brook Southampton Hospital’s annual summer gala and working with Long Island-based non-profit KiDS NEED MoRE to help raise funds during the holiday season. 

She also supports local organizations such as Project Most and ARF, where she adopted her three cats. 

Insider Tips: How to Vacation in the Hamptons like a Local

With authentic local experiences being a priority for many vacationers this year, we asked Vanessa to share a few can’t-miss activities for first-time visitors.  

“I always love to catch a film at the Sag Harbor Cinema and ice skating at Buckskill Winter Club during the off-season. The LongHouse Reserve sculpture garden is always so peaceful and is especially beautiful during cherry blossom season,” Vanessa recommends. 

Paddleboard off Havens Beach, visit the driving range at Poxabogue golf course (a real, local hangout spot), take a nature walk around the Duck Pond off of David’s Lane, or charter a boat, a personal favorite activity of Vanessa’s, with Yacht Kelpie.

Must-visit iconic Hamptons restaurants include The 1770 House, The Beacon, Sen, Tutto Il Giorno, The American Hotel, Coche Comedor, and Lulu Kitchen & Bar. Visit the Clam Bar for lunch and always order the sweet potato fries as a side, and an excellent spot for lobster rolls is Hooked in Montauk.

She also recommends the tasting room at Sagaponack Distillery, but if you’re a wine lover, head to the tasting room at Channing Daughters Winery. Si Si at EHP Resort is a great place to enjoy live music and cocktails while watching the sunset. 

“Dedicate some time to taking a leisurely drive throughout the area. Comb through the hamlet of Springs in East Hampton and discover off-the-beaten-path restaurants. Take your time exploring the village of Sag Harbor, pop into the local businesses and say hello, and take walks along the many beaches out east.”

Experience the Easy-Going Lifestyle of the Hamptons

Vanessa encourages visitors to spend time exploring the hamlets and villages, the bay beaches, nature reserves, marinas, and historic streets of the Hamptons.

“The lifestyle overall is still subdued and easy-going, and most individuals here are very friendly and welcoming. It is so much more than a vacation spot for the rich and the famous, which only makes up a small percentage of what the community is really made of.”

This article Welcome to the Hamptons, the Exclusive Retreat of Long Island’s East End originally appeared on Wander With Alex. Featured Image Credit: Vanessa Gordon


Alexandrea Sumuel is a nationally syndicated travel writer and founder of the Wander With Alex travel blog. Her work has appeared on MSN, YAHOO!, Euronews, and FOX, ABC, and NBC affiliates across the United States. 

Alex travels to experience, eat, explore, and occasionally escape! She collaborates with destinations, vacation property management companies, and hospitality technology firms to provide her readers with exclusive insights and information.