Sail Selina II Will Return to Shelter Island for 100th Year, Guided by a Family Legacy

After 25 years sailing out of St. Michaels, Maryland, the 41-foot wooden vessel will return this spring to the East End waters where she was built, just in time for her 100th anniversary in 2026. The centennial homecoming to Greenport and Shelter Island will mark both a milestone for the historic boat and a personal turning point for Captain Luna Crowley.

Crowley is the great-granddaughter of legendary Montauk charter captain Frank Mundus, the larger-than-life fisherman often cited as an inspiration for the crusty seafarer in Peter Benchley’s Jaws. Yet when Crowley talks about legacy, her voice softens not at the mention of her great-grandfather, but at the name of her great-aunt, Pat Mundus.

“She’s my lifetime mentor,” Crowley said. “I was kind of her chosen daughter.”

Before she was a licensed captain, before the centennial celebrations and charter bookings, Crowley was a 17-year-old from Massachusetts who spent summers on the East End. Pat Mundus, daughter of Frank Mundus, asked her parents if she could take Crowley on a gap-year sailing adventure. The two set off from Greenport on a nine-month voyage down the East Coast, to Cuba and the Bahamas — just the two of them.

“I knew how to day sail,” Crowley recalled. “But I didn’t know how to tie knots. I didn’t know the rules of the road.”

Pat Mundus made sure she learned. Set and drift calculations every 30 minutes. Bowline knots tied behind her back. Lessons that felt, at 17, like torture — and later, like gifts.

By 18, Crowley had enrolled in a captain’s course, one of only two women in a class of 24. During lunch breaks, she called her aunt for reassurance. When she earned her license — later upgrading to a 100-ton master with a sailing endorsement — she carried with her not just a credential, but a lineage of seamanship rooted on the North Fork.

Now that lineage converges with Selina II.

Built in 1926 at Sweets Shipyard in Greenport for the Samuel Hird family of Dering Harbor, the 41-foot, 6-inch catboat — one of only four catboats over 40 feet ever built — is believed to be the largest surviving vintage Crosby catboat. She spent her first 75 years on East End waters before relocating in 2001 to St. Michaels, Maryland, where Captain Iris Robertson sailed more than 11,000 charters.

As Selina II approaches her 100th birthday in 2026, Robertson is retiring. The boat will remain in her family trust and be passed down to the next generation, while Crowley launches Sail Selina NY, operating intimate six-passenger charters from Greenport and Shelter Island. Ownership of the Selina II will be passed to Jeff and Selina Truelove of Greenport. Selina Truelove’s parent’s and grandparents live in Dering Habor; it’s a family with deep roots in the region.

“It’s not a replica or a museum piece,” Crowley said. “She’s a living, working boat.”

For Crowley, returning Selina II to the North Fork feels symbolic at a time when the East End is evolving. Restaurants change. Prices climb. Development spreads eastward. Yet amid that transformation, she sees room — and need — for what she calls “slow craft.”

“You don’t get a 100-year-old boat without a solid foundation,” she said. “And you don’t get to keep her beautiful without loving care.”

That ethic mirrors the lessons instilled by her great-aunt: patience, precision, respect for the water. While Frank Mundus remains a South Fork legend, Crowley says it is Pat Mundus who shaped her path — a woman navigating commercial waters in the 1970s, serving as a celestial navigator for Exxon oil tankers and mentoring generations of female captains.

Despite progress, Crowley acknowledges the challenges of working in a male-dominated industry. As a young captain, she still fields the occasional dismissive remark from dockside skeptics. But she views it as part of a longer arc.

“If it were easy, it would’ve already been done,” she said. “My aunt dredged the path for me. Now it’s my turn to keep passing that baton.”

This spring, Crowley will help sail Selina II north for her centennial homecoming, weather permitting, with plans for historic tours, sunset sails and special events marking 100 years afloat.

For Crowley, the journey is both forward and back — toward a new chapter of stewardship, and toward the porch in Greenport where she once watched wooden boats launch beside her great-aunt.

“I grew up in the shadow of these stories,” she said. “To bring this boat home, to stand at the helm as another woman captain in this family — it feels full circle.”

For more information, visit sailselinany.com.