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Hamptons.com
April 14, 2025

From Shelter Island to Shinnecock: The Boating Life Returns

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T.J. Clementeby T.J. Clemente
in Community, Trending
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From Shelter Island to Shinnecock: The Boating Life Returns I Photo Credit: T.J. Clemente

It’s that time of year again—boats are being prepped for launch. Shrink-wrap is being peeled off, boat bottoms are being painted, decks are being cleaned and polished, and teak is being spruced up for the upcoming 2025 boating season. In recent years, East End boating has seen a major resurgence. On summer days, you’ll spot majestic sailboats, sleek powerboats, and multi-million-dollar yachts cruising through Gardiner’s Bay or slipping in and out of Shelter Island, Sag Harbor, the Shinnecock Canal, Montauk Harbor, Hampton Bays, and Three Mile Harbor.

 

For some, getting a boat ready is a labor of love. Others hire professionals to handle the labor-intensive job of making a boat seaworthy after months out of the water. Each year brings new developments, and in 2025, one notable addition is the creation of “Swans Marina,” located at 10 Boatyard Road, East Hampton. Local resident Dane Riva has leased the property formerly known as Vanderveer’s Boat Yard and is now actively offering summer slips at $170 per foot. Additional services include haul-outs, launchings, and winter storage. 

 

For many, the waters surrounding the Hamptons remain unfamiliar territory. Homeowners and renters typically enjoy the beaches and parks and revel in the magic of a Hamptons summer. But another layer of the experience lies offshore—aboard a recreational vessel. The idea of being free at sea holds a unique appeal for those who spend too many days under the pressure of pursuing career success. For example, while sailing, it’s the pure pleasure of catching and harnessing the power of the wind that frees the mind from its usual mental clutter.

 

Albert Einstein found relief and joy sailing around Long Island in a modest 17-footer. He once said, “A ship is always safe at the shore, but that is not what it is built for,” and described his sailing approach as, “Set sail, make it fast, no thoughts of energy or velocity, loll back, let the boat drift.” Billionaire Paul McCartney has often been seen sailing a Sunfish near Albert’s Landing in the Springs—sometimes with a daughter or his wife, Nancy. He says it relaxes him. Meanwhile, billionaire David Geffen has anchored his 453-foot yacht Rising Sun in Gardiner’s Bay for weeks at a time. The message is clear: no matter your wealth, the waters of the Hamptons can be enjoyed both simply and extravagantly.

 

Of course, any discussion of East End boating must include fishing. It’s a time-honored tradition in the region. Every fisherman has a system, a favorite spot, and a deep connection to his boat—often considered a true fishing partner. Recreational fishing boats range from multi-million-dollar vessels to modest setups costing just a few hundred dollars. Fishermen are a special breed, marked by patience and a unique bond with nature—something only countless peaceful hours at sea can foster. It touches the soul.

 

That said, boating isn’t for everyone. For some, it feels like being trapped in someone else’s floating sandbox. This author felt that way too—until sailing solo changed everything. Out on the water off East Hampton, with only the sound of wind in the sails, came the discovery of something beautiful. Offshore, the cool breeze, the vast sky, the sun, and the fast-moving clouds offer a slice of heaven. The nightly Hamptons sunsets are breathtaking, the salt air is rejuvenating, and the views—of bluffs, beaches, homes, and lighthouses—never get old. They keep the soul feeling young.

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If you've been following the fashion world on social media, chances are TOCCIN has already caught your eye. The label founded by husband-and-wife duo Alex and Michael Toccin has built a devoted following online and an even more devoted one in real life, with women who don't just love the clothes but come back for them season after season. This summer, they made it official in the Hamptons with the opening of their first freestanding store at 44 Main Street in Southampton, and it is everything you'd expect from a brand built on genuine personal connection.

TOCCIN Opens Its First Store in Southampton

If you’ve been following the fashion world on social media, chances are TOCCIN has already caught your eye. The label founded by husband-and-wife duo Alex and Michael Toccin has built a devoted following online and an even more devoted one in real life, with women who don’t just love the clothes but come back for them season after season. This summer, they made it official in the Hamptons with the opening of their first freestanding store at 44 Main Street in Southampton, and it is everything you’d expect from a brand built on genuine personal connection.

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If you only have 12 hours in Montauk, here's exactly where I'd take you. Start the morning at Marram with a coffee and a pastry. Contrary to popular belief, Marram isn't just a beachside hotel — it's also one of my favorite spots for breakfast, lunch, or an afternoon drink. I love grabbing a quick bite, sipping my coffee, and watching the morning surf lessons. If I need to answer emails or get a little work done, it's one of the best places in Montauk to open up my laptop.

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If you only have 12 hours in Montauk, here’s exactly where I’d take you. Start the morning at Marram with a coffee and a pastry. Contrary to popular belief, Marram isn’t just a beachside hotel — it’s also one of my favorite spots for breakfast, lunch, or an afternoon drink. I love grabbing a quick bite, sipping my coffee, and watching the morning surf lessons. If I need to answer emails or get a little work done, it’s one of the best places in Montauk to open up my laptop.

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  • @fellinicoffee pop-up at the @themaidstonehotel serving delicious coffee Friday through Sunday ☕️

#fellini #coffee #easthampton #summer #popup
  • Discovering incredible artists and inspiring artwork at the Hamptons Fine Art Fair. 🎨✨ 

From stunning contemporary pieces to unforgettable creative talent, this is a must-visit for any art lover. 
On view now through July 12. #fineart #art #artist #hamptons
  • Stopped by at @themontaukgeneral where we talked to the owner @kidiament about the stores best selling merchandise
#Matcha #montaukgeneralstore #hamptons
  • 🎤 Darren Criss at WHBPAC
📅 Saturday, July 11 | 8 PM
WHBPAC
76 Main St, Westhampton Beach, NY

Darren Criss takes the WHBPAC stage with music from Glee, Starkid, Broadway productions, and more. 

🎨 Hamptons Fine Art Fair
📅 Thursday, July 9 – Sunday, July 12 | 11 AM–7 PM
📍 Southampton Fairgrounds
605 County Rd 39, Southampton, NY

Explore work from more than 500 artists!

🏄 28th Annual Rell Sunn Surf Competition
📅 Saturday, July 11 | 8 AM–6 PM
📍 Ditch Plains Beach
6 Deforest Road, Montauk, NY

Celebrate one of Montauk’s beloved traditions with the local surf community. 

🛍️ Normal New York Pop-Up
📅 Friday, July 10 – Sunday, July 12 | 4 PM–8 PM
📍 The HUB
2183 Montauk Hwy, Bridgehampton, NY

Discover a curated weekend of fashion, design, vintage finds and more.

🌿 5th Annual Springs Garden Party
📅 Saturday, July 11 | 4 PM–7 PM
📍 248 Old Stone Hwy, East Hampton, NY

Enjoy cocktails, seasonal hors d’oeuvres, live music, an auction, and a raffle.

🍧 JohnnyPops Market Pop-Up
📅 Friday, July 10 – Saturday, July 11 | 10 AM–2 PM
📍 Amber Waves Farm
367 Main Street, Amagansett, NY

Enjoy a scavenger hunt, wildflower crowns, art activities, and more!

🍦 Discover La Mer Crèmery
📅 Friday, July 10 – Sunday, July 12 | 11 AM–5 PM
📍 273 Main Street, Amagansett, NY

Experience La Mer’s iconic skincare collection, samples, and indulge in gourmet ice cream.

💎 Kendra Scott Destination Color Pop-Up
📅 Saturday, July 11 – Sunday, July 12 | 11 AM–6 PM
📍 The Surf Lodge
183 Edgemere Street, Montauk, NY

Create personalized jewelry with colorful stones, metals, and charms!

⚽ World Cup Celebration with Clase Azul
📅 Friday, July 10 | 6 PM–9 PM
📍 Si Si
295 Three Mile Harbor Hog Creek Road, East Hampton, NY

Celebrate the World Cup with signature cocktails, guided tastings, and more.

🛋️ Saved New York Trunk Show
📅 Saturday, July 11 – Sunday, July 12 | 11 AM–7 PM
📍 il Buco Vita
225 Main Street, Amagansett, NY

Shop luxurious cashmere throws, pillows, antique lamps and more. 

🍸 Bar Rêve Residency a
📅 July 9- 12 | From 5 PM⁠
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Silu signature cocktails inspired by the season.⁠

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  • Last week, the @southampton_cultural_center kicked off its Summer Concert in the Park series with the legendary @nancyatlas. Before taking the stage, we caught up with Nancy to talk about her favorite places to perform in the Hamptons.
  • There are few things in life more disappointing than ordering a “healthy” lunch and getting something that tastes like punishment.

So when I stopped by Round Swamp Farm and grabbed the steak lettuce wraps in an effort to eat healthier, my expectations were somewhere between “This will be fine” and “I guess I should just eat a salad.”

I was completely wrong. These things are ridiculous. Tender, flavorful steak wrapped in crisp, fresh lettuce with just the right amount of seasoning and crunch. It’s the kind of meal that makes you forget you’re eating low-carb.

Round Swamp is an absolute madhouse. You’ll run into your neighbor, your coworker, and probably half the town. Everyone descends on this place. At Round Swamp, you’re lining up for chicken fingers, steak sandwiches, and some of the best prepared food on the East End.
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