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

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.