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
Southampton & East End Housing Crisis: Why Rents Are Out of Reach
Affordable housing has become one of the most urgent issues in Southampton, the East End, and New York City. A new report from the National Low Income Housing Coalition confirms a startling reality: there isn’t a single state, or county where a full-time minimum wage job can cover the cost of a modest two-bedroom apartment.
What This Means for Southampton
In Southampton Town, local workers, teachers, nurses, firefighters, restaurant staff can’t afford to live where they work. Rising demand for vacation rentals has pushed year-round residents out, forcing many to commute long distances or leave the East End entirely.
The East End Rent Crisis
Across the Hamptons and the East End, modest rentals are disappearing. Apartments that once housed families year-round are now marketed as summer homes at triple the price. Even a one-bedroom apartment is out of reach for many hardworking locals.
The NYC Housing Wage Gap
The problem is just as severe in New York City, where the average rent is now above $3,500. The median renter wage falls far below what’s needed, leaving millions of New Yorkers severely rent-burdened, spending more than half their income on housing alone.
Why It Matters
Affordable housing isn’t a luxury, it’s the foundation of community life. Without it, schools struggle to keep staff, small businesses can’t find employees, and younger generations are forced to move away. Projects like those led by the Town of Southampton Housing Authority are making a difference, but the need continues to grow.
Real Talk, Real People
No one should have to work 116 hours a week just to afford a modest home. If we want Southampton, the East End, and New York City to remain thriving communities, we need bold action, higher wages, smarter zoning, and more affordable housing.
📖 Read the full Out of Reach 2025 report: NLIHC.org/oor
👉 Real Talk, Real People: What’s your housing story here on the East End or in NYC? Join the conversation on my social media. Instagram and Facebook @Hamptonsmp
Labor Day comes and goes, and then—poof! Just like that, the Hamptons transforms from the center of the universe to something that feels a lot more like Mayberry. Around here, we call it Tumbleweed Tuesday—that magical day when the traffic disappears, the beaches empty, and locals can finally reclaim their towns.
From Chaos to Calm
On Monday, you can’t get across Main Street in Sag Harbor without risking your life in front of a Range Rover. The lines at the bakery wrap around the corner, and parking? Forget it. You’d have a better chance winning Powerball than finding a spot on Main Street.
Then Tuesday rolls in… and suddenly, you can hear birds chirping again. You stroll into Cluckman’s in Sag Harbor without waiting, the Sag Harbor Pharmacy has zero lines, and if you sneeze on Main Street, three people don’t bump into you.
The Local Sigh of Relief
For locals, Tumbleweed Tuesday is the ultimate deep breath. We made it through another season—survived the beach passes, the dinner reservations, and the endless “Do you know where I can get a good lobster roll?” conversations. Now comes the reward: empty beaches, shorter lines, and the Hamptons at its best—slower, friendlier, and ours again.
The Flip Side
Of course, it’s bittersweet. Many restaurants start cutting their hours, some shops close until spring, and our seasonal economy slows down. But hey, at least we can make a left turn without saying a prayer first.
Real Talk, Real People
So, cheers to Tumbleweed Tuesday—the Hamptons’ unofficial holiday. We’ve earned it. Bring on the quiet mornings, sweater weather, and fall sunsets that belong to the locals.
Because after a summer of chaos, nothing feels sweeter than finding a parking spot right in front of the Sag Harbor movie theater.
After a short hiatus, Apollo in the Hamptons returned this past weekend for the first time since 2019 and it wasn’t just another summer soirée. It was a celebration of culture, history, and community that reminded us all why preserving legacy matters.
Photo credit: Danté Crichlow
For generations, there’s been a natural connection between Harlem and the Hamptons—especially through Sag Harbor’s historic Black beachfront community. This event Apollo in the Hamptons carried that thread beautifully, bringing Harlem’s heartbeat out East for one unforgettable night at EHP Resort & Marina (Si Si Restaurant) in East Hampton.
From the moment cocktail hour began, the night set the tone: mini lobster rolls, crab cake sliders, Korean chicken lettuce wraps, carne asada skewers, and yakitori Japanese sweet potato. Dinner stations followed with Moroccan halibut, spicy rigatoni, lobster Cobb salad, and couscous with veggies.
But the highlight? The dessert station! Mini sweet potato pies, mini bread pudding, and mini banana pudding—all those Harlem-inspired flavors in bite-sized form—made it feel like home. It was a perfect fusion of East End elegance and Harlem soul. Honestly, it felt like the Hamptons and Harlem were in the same place.
Music That Moved the Room
Doug E. Fresh,Photo credit: Danté Crichlow
Apollo in the Hamptons performances lit up the night: Doug E. Fresh, Crystal Waters, Dres, Chubb Rock, and a high-energy DJ Cassidy set that had guests on their feet. Then came Wé Ani—an Amateur Night at the Apollo winner who went on to place Top 5 on American Idol 2023. Her voice soared through the Hamptons air. Personally, my favorite track of hers is Disgusted, though truthfully, her entire album is worth a listen.
Adding even more Harlem flavor, Café Wha? delivered a genre-spanning set that paid tribute to the Apollo’s iconic stage and the spirit of 125th Street.
Wé Ani, Photo credit: Danté Crichlow
Real Talk with Wé Ani 🎤
I had the chance to connect with Wé Ani after the event, and her reflections were as powerful as her performance.
Hamptons Mouthpiece: Performing at the Apollo Theater is legendary—how did that experience prepare you for your journey on American Idol?
Wé Ani“I always say this: the scariest thing I’ve ever done in my life, hands down, was performing at the Apollo. Scarier even than singing for Tony Bennett at the Library of Congress in front of Stevie Wonder, Gloria Estefan, and Josh Groban. Because at the Apollo, you know at any moment you could get booed off stage. And I thought to myself, if I can handle that—if I can survive the Apollo—I can handle anything, even Simon Cowell. That experience made me fearless.”
HM: Is there anything new on the horizon that your fans can look forward to—music, performances, or collaborations?
Wé Ani: “Absolutely. I’m in the middle of rebranding my artistry and working on a lot of new music. People can definitely expect new songs and collaborations that stretch my sound in different directions. I want to reach new audiences and step into spaces that challenge me as an artist. I’m very excited about what’s coming next.”
HM: Did you get a chance to explore Sag Harbor during Apollo in the Hamptons?
Wé Ani: “I would have loved to just stick around and see what that would have been about, because I don’t get to go to a lot of places whenever I travel. Nine times out of ten, it’s hotel to venue, then back to the hotel, back on a plane or in a car. So it really means a lot when people who are native to a place give me the full experience—because then I get to go and tell people about it, which is so important for me. I’ll definitely be back, and next time I’d love the full Sag Harbor tour.
Walter Oden, Ashley Oden, Racquel Oden, Photo credit: Danté Crichlow
A Night of Support & Star Power
The crowd reflected the Apollo’s reach and influence, with notable attendees including Michelle Ebanks (President & CEO, The Apollo), Kamilah Forbes (Executive Producer, The Apollo), Joy Profet (Chief Growth Officer, The Apollo), Star Jones, Gayle King, and actor/musician Leon.
The evening was made possible thanks to generous sponsors such as The Phillips, Gibson and Dunn/Orin Snyder, Nina & Frank Cooper/VISA, and Tameem Hourani, with additional support from Apollo’s dedicated Board of Directors. Their commitment reinforced the importance of cultural institutions like the Apollo in shaping society for the better.
The Real Star of the Night
While the celebrities and performances shined, the true star was The Apollo itself. The fundraiser raised critical funds for the theater’s first full-scale renovation and restoration. This isn’t just a facelift. It’s about preserving a cultural legacy that stretches from Ella Fitzgerald’s big break to James Brown’s electrifying performances to today’s rising stars.
Real Talk, Real People ✨
I wasn’t able to attend this year, but as someone who grew up in Harlem, the Apollo has always been more than a theater. It’s the soul of 125th Street—a place where culture, music, and history converge. Preserving it means ensuring the next generation can stand on that stage, feel that same electricity, and carry that legacy forward.
So yes, Apollo in the Hamptons was about great music, celebrity sightings, and a perfect summer night. But more than anything, it was about history—keeping it alive, honoring it, and making sure the story of Black excellence, creativity, and resilience is never forgotten.
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.
