The century-old Selina II — a family heirloom with a link to LI's maritime past — sails home to the North Fork

Flashes of golden light catch the rich, varnished wood and creamy white sail as the Selina II gently bobs along Shelter Island’s Dering Harbor. A crew of three women reef the sail to steady the boat on a gusty late spring afternoon. 

The 44-foot wooden sailboat has just arrived on the East End by way of Annapolis, Cape May, Manasquan and Port Washington.  

But in Peconic Bay, she is truly at home.

Built in Greenport in 1926, the Selina II spent 75 years in Dering Harbor before moving to Chesapeake Bay in 2001. After 25 years as a charterboat, Capt. Iris Robertson sailed her back north to pass her to the fourth generation: Robertson's niece, Selina Truelove, and husband, Jeff, of Greenport. The couple enlisted Capt. Luna Pearl Crowley to run charters, giving guests an up-close look at a Gatsby-era yacht.

The catboat is both a family heirloom and living piece of maritime history. It harkens back to an era when the working waterfront defined the East End, a way of life that dwindled as shipyards, including the one where the Selina II was built, were redeveloped into waterfront condominiums.

Commissioned by Robertson’s grandfather, Samuel Hird, the Selina II was built at the now-defunct H.W. Sweet Shipyard a century ago. Named for Hird's mother, women in the family have taken a prominent role in keeping her seaworthy in the century since.

Sailing along Shelter Island’s north side, Robertson points out a slice of land Hird sold off to afford the $10,000 endeavor, a second attempt at a family pleasure boat.

“The first boat hadn’t worked out for them,” she said, describing the skinny, tippy Selina I that couldn’t stand up to the turbulent Plum Gut. “My grandmother’s on board with the kids … she was terrified, there’s water slopping in.”

Soon enough, that boat was history. What came next has endured for 100 years.

Robertson, 67, explains the boat is designed to be half as wide as it is long for stability — a selling point that made her grandmother feel safe.

The Selina II was one of four catboats built measuring over 40 feet and the only one known to still be sailing, according to Robertson.

Meticulous care is the primary reason the boat has outlived her peers. Annual maintenance can top tens of thousands of dollars.

“Sometimes we change out a plank or two or three,” Robertson said. “There have been years where I have not had to do any planking. Each year is its own creature.”

There are several new additions — a second wheel, third mast, second boom — but Robertson points out that much is original, including the mahogany cockpit and blocks used to raise her 1,000-square-foot sail.

Robertson decided to put the boat in the charter business and estimates she took 60,000 guests sailing in her 25 years as captain.

“It’s not a static display, it’s a living piece of American maritime history, and I’m proud that I’ve been part of it,” she said.

At Robertson’s urging, the Trueloves are keeping Selina II in the charter business. “That way, it’s not a burden, but a joy,” Robertson said.

Mundus family roots

Crowley, 27, is already deeply ingrained in the region’s maritime history as a third-generation captain.

Her great-grandfather was Frank Mundus, the legendary Montauk fisherman widely believed to be the inspiration for the character Quint in "Jaws." But she was most impacted by her great-aunt, Pat Mundus, of Greenport, a retired oil tanker captain.

At 18, Crowley took a gap year with Mundus and spent nine months on her 57-foot sailboat, Surprise, sailing down the East Coast to Cuba and the Bahamas.

“She was a celestial navigator for Exxon oil riggers back in the '70s, when women weren't really even on the ships, never mind third in charge,” Crowley said. “She’s made it a point to mentor women captains.”

On the voyage, there were idyllic moments: spearfishing along reefs, trading freshly caught lobsters with other sailors for new DVDs to watch.

Mundus also challenged Crowley to tie bowline knots behind her back, change oil, and plot courses to navigate. As soon as Crowley returned, she began studying for her captain’s license.

“I grew up on sailboats, but I didn't know how to tie knots, and I didn't know the rules of the road,” Crowley said. “It was a super crash course in seamanship. It changed my life.”

Now, captaining Selina II is an honor, Crowley said. In a nod to Mundus and Robertson, she’s hired an all-women crew, including first mate Haley Mae Mason.

“We're showing that we have space here too, and I'm really grateful for Capt. Iris and for Capt. Pat Mundus, for dredging the path,” Crowley said. “It’s my turn to … make it accessible for young girls to feel like they can do it, too.”

Crowley plans to host charters of up to six guests for a range of activities, from family day sails and sunset cruises to proposals and microweddings.

Most of all, she’s eager to share the simplicity of sailing with others: cutting the engines and just listening to wind and water.

'The workhorses of Greenport'

Selina II’s return to the East End is a welcome dose of nostalgia in a harbor increasingly filled with large, luxury fiberglass yachts.

“Sailing is the opposite of instant gratification,” Crowley said. “It's totally about being present.”

Since returning to Shelter Island, the sailboat has drawn attention from longtime residents who remember seeing her 50 years ago.

“Catboats were the workhorses of Greenport and the surrounding bays,” said Erin Kimmel, the executive director at the East End Seaport Museum. Kimmel said the preservation of boats like the Selina II is meaningful to the area’s history. “She is not a museum piece, but a living reminder of the working maritime culture that built and remains active in Greenport today.”

For the Trueloves, the next generation of Selina II’s owners, it was important to keep the family legacy going.

“It was amazing to step aboard the boat when she returned to the East End … and be brought back in time by her smell,” Selina Truelove said, referring to the vessel's complex, woody scent.

Some of her dearest childhood memories were spent on the sailboat, sitting above the transom and dragging glass-bottle “boats” on strings in her wake, and her grandfather’s relentless varnishing.

Caring for the sailboat is a “busman’s holiday” for Jeff Truelove, who works full time on wooden boats in Oyster Bay and is the executive director of the Stirling Harbor Foundation, a nonprofit focused on preserving maritime history through sailing.

The couple is looking forward to leading the vessel into her second century.

“That’s the beauty of wooden boats,” Jeff Truelove said. “You can replace the planking, you can replace the fasteners that hold the planking. You can replace floors and frames and engines and masts and spars, and 100 years on, you still have the same boat.”