Author: Tom Darling

It was Memorial Day 2020, and I was not sailing. Our Classics Fleet at Oakcliff Sailing in Oyster Bay, New York was restricted by social distancing and masks. All I could do for recreation was walk. It was as eerily quiet on the water as it was in the deep of The Ramble in New York City’s Central Park. I was walking daily during the spring of 2020, and realized I was not walking by myself; I…

By Tom Darling, Conversations with Classic Boats   Who has ever heard of the Barrs; Captain John Barr and his half-brother Charlie (often spelled Charley)? Captain John steered some of the most famous offshore yachts in Britain and America. Younger brother Charlie, in league with Nat Herreshoff, took the helm of a succession of America’s Cup defenders in the Gilded Age culminating with the mighty Reliance in 1903. In this issue, we’re presenting original research gathered from…

Last summer we took a trip down the trail of my family’s yachting history, to the fabled hub of New York yachting, City Island. We learned in our research that many of the skilled workers in the shipyards and sail lofts were immigrants. Several were Scots. Much of what has created American yachting tradition came from the British Isles, predictably from England and, surprisingly, a wee bit more from Scotland.     The Solent and the Clyde…

By Tom Darling, Conversations with Classic Boats     Go back and look at your favorite James Bond movie, preferably with Sean Connery. Chances are there’s a glamorous wooden inboard boat involved. She’s an elegant mahogany-sided speedboat with a unique back seat, a sunning platform, that bobs at the waterside. Most likely she’s a Riva, the motorboat that hearkens back to the 1960 Federico Fellini film La Dolce Vita. Riva powers on today, with many owners also…

6 Metre Pre-Worlds a preamble to the 2025 Worlds By Tom Darling, Conversations with Classic Boats Photos by Peter D. Taylor When I heard that an iconic meter boat collection was coming to Oyster Bay, New York, the historical hub of 6 Metre sailing in the U.S., I was all ears. Earlier articles about on the development and growth of the International Six Meter (Metre) yacht appeared on these pages in 2021 and ’23; online at windcheckmagazine.com/article/a-century-of-sixes/…

“It’s not history. It’s fiction based on fact.”     The story of the schooner, America’s first iconic yacht design, often follows along fanciful story lines. From the original America, namesake for the Cup that’s launched a hundred campaigns, to working fishing boats and more recently built craft constructed with modern materials, the schooner is a design mystery tucked in a long-lost history book. What makes a schooner a schooner? It’s a sailboat built with a minimum…

August, midsummer. It is THE season. Art shows, antiques shows, car shows and of course, boat shows. We are not visiting boat shows to kick the tires or buy a boat; we are touring collections of vintage, usually all wooden, boats brought by their owners for viewing by the boating public. We’re talking about an Antiques Roadshow of floating vintage wood. There are many such shows but we have picked two, one about as far east as…

New York City’s boating history comes alive at the City Island Nautical Museum   In late June, I took a trip down a personal nautical memory lane. My cousin Peter Taylor, a talented marine photographer, and I drove over the bridge, first built in 1874, from the Bronx mainland and crept down City Island Avenue, the island’s main north-south artery. We were looking for the City Island Nautical Museum at 190 Fordham Street because we have family…

At the end of the North Fork of Long Island, there’s a fishing and boating town called Greenport. For most, it’s the jumping off point via ferry for Shelter Island, long past its origins as a sleepy Quaker refuge. Shelter Island is home to the largest concentration of classic boats out East. That fleet numbers as many as fifty fiberglass Doughdish sloops, Cape Cod Shipbuilding’s transcription of Herreshoff’s most prolific 1914 design, the Herreshoff 12 ½. At…

Reliving the Past in Intercollegiate Sailing We learned in the recent streaming series on the New England Patriots, “The Dynasty,” that a true dynasty team needed to have at least three successive championships in four attempts to be described with the D-word. The 1960s Boston Celtics, the ‘80s LA Lakers, and ‘90s Chicago Bulls come to mind. In the mid-1970s, in the very early days of Women’s intercollegiate sailing, one team made that grade and went one…