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May 1, 2013

Sailing The Hamptons: Two Boats Take On The America’s Cup

T.J. Clementeby T.J. Clemente
in Entertainment
Home Entertainment

I am so excited that spring is rolling in and soon my sailboat will be again sailing on Gardiner’s Bay. Out on the water’s that surround the East End and The Hamptons are always many amazing boats. There are huge ocean capable powerboats as well as small character-building sailboats. This story is about two majestic sailboats, one that won an America’s Cup final, and another that lost.

Out on the water’s that surround the East End and The Hamptons are always many amazing boats. (Courtesy Photo)

I was sailing on my 22’ Catalina (Caelan Shea) a few years back when I saw this amazing sailboat crisscrossing Gardiner’s Bay with ease. The mast was over 100 feet high and the lines of this boat where right out of a sailing museum photo. Sure enough later that evening I was informed it was “Endeavour” which had sailed from Newport to Sag Harbor that very day. Endeavour is one of the greatest of ten J-Yacht class boats ever built. However, it lost the 1934 America’s Cup Race to Harold Stirling Vanderbilt’s J-Yacht “Rainbow.” That afternoon, Endeavour was a sight of beauty as it danced elegantly all over Gardiner’s Bay. Endeavour has quite a history, I read up about how the boat was about to be scraped after sitting in an abandoned seaplane base in southern England, this after having changed hands many times over 47 years. It was saved in 1984 and the hull was “flown” to New Zealand and then restored back to what it once was, the most beautiful J-boat ever built.

When I told life-long Southampton local, Swede Edwards, of North Sea Radiator, about seeing Endeavour he mentioned that his dad had been part of the crew of Harold Stirling Vanderbilt’s 1937 America’s Cup winning J-Yacht “Ranger.” Ranger actually defeated Endeavour II, the successor of Endeavour, to win the 1937 America’s Cup off Newport. Swede told me George Monsell of Greenport was a captain of the Ranger crew for Harold Vanderbilt when he wasn’t onboard. After securing the 1937 America’s Cup, Harold Vanderbilt dismantled the winning boat, Ranger, to build the next one. But a part of Ranger still lives on!

I spoke with a second-generation relative of George Monsell this week, who verified that just before World War II (1940ish) the ornate cabins of two bedrooms of the Yacht Ranger were preserved and removed by Mr. Monsell. He had them moved to Norwold Lane in Cutchogue on the North Fork, where a cottage was built around them. Today, over 70 years later, that cottage is rented and still owned by the descendants of George Monsell. I was told the wonderfully crafted wood bedrooms are intact and in great shape.

Lastly, there now exists a replica of Ranger that was built at Danish Yacht Boatyard in early 2002 and completed in late December 2003 and does tours all over; including Sag Harbor and Greenport. I really can’t wait to get back on the water and start sailing the 2013 season.

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R.AIRE Wine Dinner with Emilio Moro

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Buying The Hamptons:  Get A Buyers Agent

Buying The Hamptons: Get A Buyers Agent

  • When: Fri, Oct 3rd – Sun, Oct 5th, 2025
8am – 5pm

Where: Levain Bakery, 354 Montauk Hwy, Wainscott, NY

Levain Bakery is introducing a new cookie for a limited time: Peanut Butter Dark Chocolate Chip – a decadent mix of creamy and chunky peanut butter with rich dark chocolate chunks. Originally created to celebrate the opening of Levain’s Beverly Hills Bakery, this indulgent new flavor will now be available for just three days only, October 3–5, at all retail bakery locations.

To make the weekend even sweeter, guests who purchase a cookie will receive a Levain Bakery mini tote (while supplies last), a fan-favorite collectible sure to go quickly.

#levain #levainbakery #cookie #minitote #tote #hamptons
  • From world premieres at the Hamptons International Film Festival to SouthamptonFest! ⁠
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Check out the Top Hamptons Events This Weekend!⁠
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🎬 33rd Hamptons International Film Festival⁠
📅 Oct 3 – 13, 2025 | 9AM – 10PM⁠
📍 Various Locations⁠
A global lineup of films, shorts & documentaries.⁠
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🍪 Levain Bakery⁠
📅 Oct 3 – 5, 2025 | 8AM – 5PM⁠
📍 354 Montauk Hwy, Wainscott⁠
Try the Peanut Butter Dark Chocolate Chip cookie + snag a mini tote (while supplies last).⁠
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🎉 13th Annual SouthamptonFest⁠
📅 Oct 3 – 5, 2025 | 10AM – 7PM⁠
📍 Southampton Village⁠
Arts, culture, food & family fun all weekend long!⁠
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🎶 SpringsFest⁠
📅 Oct 4, 2025⁠
📍 1 Parsons Pl, East Hampton⁠
Live music, raffles, crafts, blacksmith demos & more.⁠
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💃 Salsa Social @ The Clubhouse Hamptons⁠
📅 Oct 4, 2025 | 9PM – 11:30PM⁠
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Dance the night away w/ DJ Chile & more!⁠
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🐚 34th Annual Largest Clam Contest⁠
📅 Oct 5, 2025 | 12PM – 3PM⁠
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Taste clam chowder, clam pies & cheer on the winners!⁠
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🎷 East Meets West Jazz Jam Session⁠
📅 Oct 5, 2025 | 2PM – 5PM⁠
📍 Southampton Cultural Center⁠
Free community jazz jam – all are welcome.⁠
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🌕 Full Hunter’s Super Moon Hike⁠
📅 Oct 6, 2025 | 6:30PM – 7:30PM⁠
📍 SOFO Museum Parking Lot⁠
Guided evening hike under the moonlight.⁠
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✨ Which event are you most excited for?⁠
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#hamptons #hamptonsinternationalfilfestival #hiff #jazz #fullmoon #hike #film #levainbakery #community
  • So many fun fall activities in the Hamptons 🎃

@fairviewfarmatmecox 
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#hamptons #fall #applepicking🍎 #pumpkin #maze #pettingfarm
  • As summer winds down and the cool breezes of fall approach, jewelry enthusiasts and fashion lovers alike are looking for the latest seasonal trends. Yael Fraynd, founder and president of Yaya Publicity, offers an insider’s perspective on what to expect this fall — especially for those embracing the chic lifestyle of the Hamptons.⁠
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Looking ahead to fall, Fraynd described the evolving styles with enthusiasm. For fall, expect to see bold statement pieces, rich gemstone colors like orange and a playful mix of metals. ⁠
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📸: Photo Credit: BFA/Madison McGaw⁠
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#lagence #fashion #sagharbor #hamptons #bluandcream
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