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Real Talk on Housing the Hamptons

The Hamptons is beautiful, but beneath the sunsets and sailboats, the East End is struggling with a housing crisis that affects everyone. This isn’t about traffic or celebrity real estate. It’s about where the people who keep this community alive can afford to live. Teachers, doctors, nurses, hospitality staff, and tradespeople are driving two hours each way just to make the Hamptons work. That is not sustainable, and it is not fair.

If you live or work anywhere from Westhampton to Montauk, you can see the imbalance and a real housing crisis. Homes worth millions sit empty most of the year while workers struggle to find a one-bedroom apartment they can afford. A healthy community needs all kinds of people, not just those who can afford luxury real estate. The Hamptons runs on real people with real jobs, and we need real solutions to keep them here.

Rents across the East End have soared, with $3,000 to $6,000 a month now considered normal. The average worker earns $50,000 to $70,000 a year, which makes those rents impossible. Add in bridge closures, construction, and traffic, and workers spend more time commuting than being home with their families. We can and must do better.

Here’s how we start making housing work for everyone on the East End.

  • Build smarter, not just bigger. Support mixed-income developments and creative reuse projects. Convert unused buildings, vacant motels, or municipal spaces into year-round workforce housing. This keeps local character and creates attainable homes faster.
  • Empower local housing authorities like TSHA. The Town of Southampton Housing Authority is showing that real progress is possible with projects like Watermill Crossing and Sandy Hollow Cove. Let’s expand those models across every East End town with public-private partnerships.
  • Incentivize landlords to accept housing vouchers. Create tax incentives and grants for property owners who rent to potential tenants using HUD or Section 8 vouchers. This opens doors for working families and helps stabilize neighborhoods with reliable, long-term residents.
  • Encourage homeowners to build accessory dwellings. Offer financial assistance, reduced permit fees, or tax rebates to homeowners who create small rental units on their property for essential workers such as teachers, doctors, nurses, hospitality, retail, and trade employees. These accessory dwellings help fill the desperate housing gap while giving homeowners a steady income stream.
  • Incentivize year-round rentals. Offer property tax credits or local grants for landlords who rent year-round instead of seasonally. This builds stability for tenants and ensures that local businesses can count on a consistent workforce.
  • Improve transportation and access. Reliable, year-round public transit and carpool programs can reduce commute times, cut costs, and improve quality of life for workers traveling from outside towns.
  • Change the narrative. Affordable housing does not lower property values. It raises community values by keeping neighborhoods diverse, strong, and thriving.

Everyone says they support affordable housing until it is time to approve a project near them. Real talk: that has to change. The East End needs collaboration between towns, nonprofits, builders, and residents to turn words into action. When we all work together, we can create housing that reflects our values and supports the people who make this community work.

Imagine a Hamptons where teachers live near their schools, nurses have apartments close to the hospitals where they work, and restaurant staff can afford a place nearby instead of sleeping in their cars. Imagine seniors being able to downsize locally and young professionals buying their first home without leaving the area. That is not a dream. It is entirely possible if we start treating housing as a community priority, not a luxury commodity.

We all will, together. Because this is not about charity. It is about community. When people can live where they work, they invest, they participate, and they stay. That is how you keep a community alive. The Hamptons does not have to lose its heart to wealth. It just needs to remember its people.

Real Talk. Real People. Real Solutions. The East End can do this if we choose to.

  • Support local workforce housing projects from TSHA, CDC of Long Island, and other organizations.
  • Attend zoning and planning meetings and make your voice heard.
  • Encourage your town board to fund incentives for landlords who accept vouchers and homeowners who build accessory dwellings.
  • Volunteer or donate to Sag Harbor Food Pantry or Sag Harbor Helpers.

If you love the Hamptons, fight for the people who make it home. Real talk, real people



What happens when a U.S. Marine with 20 years of service trades global deployments for go-bags and disaster radios? You get Drew Jennings, founder of Outpost Preparedness, who’s redefining what it means to be ready when life throws you a curvebal or, here in the Hamptons, a hurricane.

From the Battlefield to the Backyard

Drew Jennings, spent the first ten years of his military career in infantry and the next ten in aviation logistics, sourcing global teams and leading through chaos, pandemics included. So, when he says “know your circumstances,” he means it.

Every family is different, he explains: “Some folks have ADA needs, medication, kids, dogs… preparedness looks different for everyone.” His company’s mission is to help people identify their specific vulnerabilities before crisis hits. Because once disaster strikes, whether it’s a coastal storm or a power outage, it’s too late to start Googling “what’s in a go-bag.”

Why the Hamptons Needs to Hear This

Out here on the East End, we like to think we’re insulated from the world’s mess. But anyone who’s lived through a nor’easter knows how quickly isolation, flooded roads, and powerless nights can humble you. Drew’s message hits home:

“Insert early, prepare early,” he says. “If the power goes down, have power there readily available. If the water source is contaminated, have an alternate. That gives first responders time to reach you — and keeps panic from spreading.”

Panic, by the way, is the enemy. Drew Jennings, uses a perfect example: remember the toilet-paper frenzy of 2020? One viral post, and boom, chaos. That’s “herd mentality” in action. “Preparedness prevents that,” he adds.

Beyond Gear: Building Community Resilience

For Drew Jennings,, being prepared isn’t just about survival; it’s about solidarity. If every household has a plan and basic supplies, the entire community stays calmer, stronger, and safer.

“It’s more beneficial for each person to prepare based on their exact circumstances,” he says. “When everyone does that, we prevent chaos. We give our first responders space to do their jobs. We build resilience — together.”

In true Marine fashion, he’s leading by example. Drew and his team represent more than 90 years of combined military experience, personally field-test every kit. They’ve spent 72 hours living solely on what’s inside those bags, proving they actually work. (And yes, he has video proof coming soon.)

The Gear: Confidence in the Bag

Outpost Preparedness currently offers two main kits:

  • The Essential Go Bag ($399 pre-sale) – a 72-hour survival pack with 20-year shelf-life food, 5-year water, solar power bank, flashlight, multi-tool, and a hand-crank radio.
  • The Protector Go Bag ($699 pre-sale) – built for two people, with double the food, water, and extra supplies, the “glamping” version of survival, as Drew puts it.

Every purchase includes a one-on-one consulting session with Drew. “You tell me about your family — medications, pets, kids and I help you design a plan,” he says. Buyers also get digital guides and monthly community Q&As.

And here’s the kicker: if you ever need to use your bag during a real emergency, he’ll replace it for free.

Preparedness Is the New Luxury

In a place like the Hamptons, we plan for everything; from dinner reservations to weekend traffic. But how many of us have actually planned for a blackout or a blocked road after a storm?

Drew Jennings wants to change that. His message isn’t about fear; it’s about empowerment. “It’s not about being paranoid,” he says. “It’s about being confident, knowing that your family can endure.”

So maybe the next time you’re stocking up at Citarella, skip the extra Rosé and think about your real essentials; food, water, light, and a plan. Because resilience? That’s the real Hamptons luxury.

Learn more or order a Founders 50 Go Bag: www.outpostprep.com

Real Talk. Real People. Real Prepared.

How Sag Harbor’s Own Suzan Johnson Cook Made History and Still Makes Time for the Beach

Real talk: Some people take on roles that change their lives, and then there are those who take on roles that change the world. Ambassador Suzan Johnson Cook, known to many as Ambassador Sujay, belongs to the second category. She made history as the first Black woman and first clergywoman to serve as the United States Ambassador-at-Large for International Religious Freedom. In that role, she advised President Barack Obama and traveled the globe advocating for the rights of people to believe as they choose, free from persecution.

It is an extraordinary responsibility. Yet, here is the beautiful surprise. This global powerhouse also calls Sag Harbor home. Not just any Sag Harbor community, but Azurest, a historic and culturally significant enclave where generations of Black families found refuge and belonging long before the Hamptons became a household name.

When I sat down with Ambassador Sujay, she described her connection to Sag Harbor in a way that felt both poetic and deeply grounded.

“This is a sanctuary where you can pull back, be inspired, and sustain the woman you are becoming,” she said. “Everything that makes me who I am happens here in Azurest.” That truth is woven into every part of her story.

Sag Harbor Roots: Salt Air and Soul Work

For more than three decades, Ambassador Sujay, has been a part of the Azurest community. She raised her two sons here. She swims here. She reflects and restores her spirit here. She has created a life where the peace of this village continues to fuel her purpose.

Diplomacy on the World Stage

During her time in the Obama administration, Ambassador Sujay held responsibility for nearly every nation in the world except the United States. She was tasked with advocating for international religious freedom in 199 countries. Her work required meeting people where they are, across faiths, cultures, and political structures.

One unexpected lesson she shared with me was that the position she held had originally been shaped by and for the conservative religious right. Her presence in that space was not anticipated.

“They were not expecting me, and I was not expecting them,” she said with a smile. “But we learned how to sit at the same table for the sake of humanity.”

Ambassador Sujay also recognized the absence of women’s voices in global policy conversations and founded the first worldwide roundtable for women in religious freedom, which continues today.

There were moments that felt almost surreal, including the experience of sitting in the private prayer room of Pope Benedict. As she described it, she paused, still humbled by the memory. A Baptist girl from the Bronx, sharing a room with the Pope. It was not just history. It was an affirmation of purpose.

Live With SuJay: Amplifying Black Women Leaders

Ambassador Sujay did not limit her leadership to international arenas. She also created space for local voices, particularly Black women leaders on the East End, by launching her television program, “Live with Sujay” on LTV.

What has surprised her most is the depth of talent in this community. Every guest brings something extraordinary. She sees it as her mission to make sure these women are not only doing the work but are also being seen and heard.

Wellness as a Requirement, Not a Reward

Her beloved wellness initiative, Selah by the Sea, has been transforming lives for more than 20 years. She explained that the word “Selah,” used more than 70 times in scripture, means to pause, reflect, and rest.

Black women, she noted, are frequently the ones holding up the world, often without interruption. They are multitaskers, caregivers, executives, leaders, and community builders. Yet the world rarely encourages them to pause.

“Selah by the Sea gives women permission to step away, leave the phone behind, sit by the water, and restore what they have poured out,” she explained.

It is a reminder that taking care of yourself is not selfish. It is a strategy for survival.

Legacy: Preparing the Next Generation to Lead

When discussing legacy, Ambassador Sujay became both reflective and energized. She believes that true legacy requires forward motion.

“We stand on the shoulders of Harriet Tubman, Sojourner Truth, Dorothy Height, and Coretta Scott King,” she said. “We also stand on the shoulders of our own mothers. The next generation must be able to stand on ours. If our progress dies with us, it becomes history. When it continues, it becomes legacy.”

Her work reflects that belief. Through organizations such as Charisma Speakers, the Global Black Women’s Chamber of Commerce, and Women on the World Stage, she is building ecosystems that strengthen economic empowerment, leadership development, and global sisterhood.

She teaches women not only how to enter rooms of power but how to lead once inside. She believes legacy is about generational wealth, generational wisdom, and generational wellness.

The Ambassador Next Door

What is remarkable about Ambassador Suzan Johnson Cook is that she continues to rise to extraordinary heights without ever disconnecting from her foundation. She can meet with presidents and popes and return home to Sag Harbor with the same grace and gratitude.

She is living proof that sanctuary and purpose can coexist. She shows us that leadership does not always begin in a conference room. Sometimes it begins on a quiet walk to the beach.

Ambassador Sujay is still writing her story. The best part is that she continues to help other women write theirs.

Learn More and Stay Connected

photo credit: Antigua & Barbuda tourism

Sag Harbor was alive with energy on Saturday, August 9th, as sails filled Noyack Bay for the 15th Annual Antigua & Barbuda Hamptons Challenge Regatta. This wasn’t just another day on the water—it was a cultural exchange, a fierce competition, and a celebration of community that brought the Caribbean spirit straight to the East End.

photo credit: Antigua & Barbuda tourism

The regatta drew sailors from across the region, all vying for the coveted grand prize: an all-expenses-paid trip to Antigua to compete in Antigua Sailing Week 2026. After fifteen tries, skipper Lee Oldak and his crew on Purple Haze finally claimed victory, proving that persistence (and maybe a touch of island luck) pays off.

But here’s what makes this race different: it’s not only about winning—it’s about giving back. The Antigua and Barbuda Tourism Authority presented a $5,000 donation to i-tri, the local nonprofit that empowers middle school girls through triathlon training and mentorship. Seeing Theresa Roden and the i-tri team standing proudly alongside Antigua’s Minister of Tourism, The Honourable Charles Fernandez, was a reminder of why this regatta matters. It connects two harbors—Sag Harbor and English Harbour—that share rich maritime histories while investing in the next generation of strong, resilient young women.

After a day on the water, the celebration moved to The Bell and Anchor, where guests were treated to a Caribbean-inspired evening—rum cocktails, island cuisine, music, and plenty of dancing. It was “Caribbean in the Hamptons,” and the vibe was pure joy.

The weekend also brought Antigua & Barbuda’s hospitality to local travel advisors, with Dean Fenton, U.S. Director of Tourism, sharing how personal connections and partnerships are steering more travelers to the twin-island nation. Luxury properties like The Hut on Little Jumby Island and Blue Waters Resort & Spa added a splash of glamour to the storytelling, showing that Antigua is about both adventure and indulgence.

For me, this event was a perfect example of “Real Talk, Real People.” It’s not just a race; it’s about building bridges—between cultures, between communities, and between generations. Whether you were out on the water, cheering from the shore, or raising a glass at the gala, you felt it: the thrill of competition, the triumph of resilience, and the warmth of Antigua right here in Sag Harbor.

As the sun set over the bay, sails came down, but the memories stayed bright. And next April, when Purple Haze sets sail in Antigua, Sag Harbor will be cheering them on from 1,600 miles away.

Until then, cheers to another year of thrills, triumphs, and togetherness—Antigua style, Hamptons heart. Real Talk, Real People

If you think Sag Harbor is all about sitting dockside with a glass of rosé, you’re only half right. The other half? You need to get yourself on American Beauty II and see this village from the water. Trust me — your Instagram will thank you.

Here at Hamptons Mouthpiece, we’re all about those experiences that make you say, “Why didn’t I do this sooner?” And cruising on American Beauty II is at the top of that list.

American Beauty II is a 44-foot charmer docked right on Long Wharf. Captain Don Heckman launched this dream back in ’92 because he believed boating should be fun and affordable for everyone.

Photo courtesy: American Beauty Cruises and Charters

✨ Pick Your Cruise Mood

Private Charter – Birthday? Bachelorette? Girls’ day out? Or maybe it’s just Tuesday and you feel like it. Rent the whole boat for $630/hour (and yes, there’s a discount if you pay in cash or Zelle — we love a bargain). Bring your own snacks, drinks, and playlist. One rule: leave the red wine at home. The boat cushions will thank you.

Ticketed Cruises:

• Sunset Cruise – Two glorious hours of golden light, salty breezes, and everyone suddenly feeling like a movie star.

• Nature Cruise – 90 minutes of “oohs” and “ahhs” as you pass osprey nests, secret coves, and get the lowdown on Sag Harbor history — plus a peek at some fancy waterfront homes.

Why You’ll Love It

Photo courtesy: American Beauty Cruises and Charters

• The Vibe – Zero pretense. Just good people, good music, and good views.

• The Stories – From whaling days to celebrity hideaways, you’ll get the Sag Harbor tea.

• The Views – Sunsets so pretty, you’ll be tempted to move aboard.

Hamptons Mouthpiece Tips

• Book ahead — especially for those weekend sunset cruises.

• Arrive early so you can snag the best spot for selfies (and snacks).

• If the weather turns, no stress — they’ll reschedule or refund.

Next time you’re in Sag Harbor, trade your dinner table for a deck and your shoes for boat vibes. American Beauty II isn’t just a cruise — it’s a floating memory maker.

Real talk, real people: From the Hamptons Mouthpiece to you — get off the dock and into the story.