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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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  • Check out the Top Hamptons events This Weekend!⁠
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🎨 2026 Student Exhibition Preview Day⁠
📅 Saturday, March 7 | ⏰ 11am–5pm⁠
📍 Parrish Art Museum, Water Mill⁠
Saturday is for the arts! Enjoy exhibition previews, a drop-in drumming circle, imagination play workshops, and a performance by the Southampton String Ensemble.⁠
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🎻 Fiddler’s Green: A Traditional Irish Music Concert⁠
📅 Saturday, March 7 | ⏰ 1–2:30pm⁠
📍 Southampton History Museum, Southampton⁠
Fiddler’s Green brings the traditional music of Ireland to the East End.⁠
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🍀 Pot O’ Gold Catapult Workshop⁠
📅 Saturday, March 7 | ⏰ 3–6pm⁠
📍 Children’s Museum of the East End, Bridgehampton⁠
Kids can build a catapult and launch gold coins into the lucky pot.⁠
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🎸 Gene Casey and the Lone Sharks⁠
📅 Saturday, March 7 | ⏰ 8–10pm⁠
📍 Bay Street Theater, Sag Harbor⁠
Dubbed “the house band of the Hamptons,” the group brings their iconic country sound to the stage.⁠
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🥣 Project MOST’s Empty Bowls⁠
📅 Sunday, March 8 | ⏰ 12–3pm⁠
📍 Amagansett American Legion Post 419⁠
Taste soups crafted by local chefs while supporting vital programs for children and families. Plus live music, a 50/50 raffle, and family fun.⁠
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🎤 “Sing-Along the American Songbook” Jazz Jam⁠
📅 Sunday, March 8 | ⏰ 2–5pm⁠
📍 Southampton Cultural Center⁠
Celebrating Women’s History Month with vocalists Ludmilla Benevides and Vanessa Trouble, joined by Jane Hastay, Iris Ornig, and Carl Sarafina.⁠
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🥘 Spanish Tapas & Paella Cooking Class⁠
📅 Sunday, March 8 | ⏰ 3:30–6:30pm⁠
📍 R.AIRE, Hampton Bays⁠
Cook alongside Chef Alex, enjoy wine pairings, and dine together afterward.⁠
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🥾 Montauk Loop Hike⁠
📅 Saturday, March 7 | ⏰ 10am–12:30pm⁠
📍 Montauk Lighthouse⁠
Explore scenic trails and keep an eye out for harbor seals.⁠
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🎬 Hoppers in IMAX⁠
📍 Southampton Playhouse⁠
Follow Mabel as her consciousness transfers into a robotic beaver and she enters the animal world.⁠
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📚 BookHampton Book Club: Vigil⁠
📅 Tuesday, March 10 | ⏰ 4pm⁠
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Join fellow readers to discuss George Saunders’ newest book.⁠
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Visit Hamptons.com for more events!⁠
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#weekend #hamptons #hoppers #events #books
  • Quogue Wildlife Refuge held its beloved “Light The Night” trail walk. I’ve heard through the grapevine that the annual walk is magical, peaceful, and paints the dreaded cold winter nights in a whole new light (literally).⁠
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The community braced the cold, freezing temperatures as they followed a lantern trail and entered a quaint marketplace with a Hamptons Coffee Company booth serving delicious, complimentary hot chocolate in reusable mugs, a merch booth with an impressive selection of animal stickers, beanies, pins, maps, stuffed animals, and my personal favorite, a bandana with a map of the Refuge. A must-have for any wildlife fanatic.⁠
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📸: Quogue Wildlife Refuge & Dennis Maroulas & Hamptons.com⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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Recently acquired by Moskow Management Trust and offered fully furnished, the gated estate is exclusively represented by Vince Horcasitas of Saunders & Associates.⁠
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@vinceinthehamptons⁠
@hamptonsrealestate⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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🖼 Opening Reception: Reclaiming Death Exhibition⁠
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🕔 Saturday, Feb 28 | 5–8PM⁠
A powerful group exhibition featuring 20 artists exploring personal and cultural end-of-life practices.⁠
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🎬 2026 Oscar-Nominated Short Films at Sag Harbor Cinema⁠
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👨‍👩‍👧 Family Day at Guild Hall⁠
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🍷 Wine Wednesday at Nick & Toni’s⁠
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New to Southampton in 2026, Charlie Fox Dispensary is elevating the Hamptons’ luxury wellness/cannabis space with edibles (and drinkables) for every occasion, CBD+, premium vapes and pre-rolls, wellness topicals and remedies, the best flower in the Hamptons, and accessories you won’t have to hide when you entertain.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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