The family tree at sea — the Selina II sails home

In April, the Selina II, a 41-foot wooden catboat built in Greenport in 1926, set sail from Saint Michaels, Md., on her way back to her original home of Dering Harbor — but this wasn’t any old pleasure cruise up the East Coast. It was a voyage of generation-spanning family connection. 

Capt. Selina Iris Hird Robertson, known as Iris, was at the helm of the boat that has been in her family for exactly a century this year.

“My family has been on Shelter Island for seven generations,” Ms. Robertson said. Her great-grandfather Samuel Hird built the family’s house in Dering Harbor in 1913. Her mother, Esther Hird Hunt, of Dering Harbor, passed away in May at the age of 102, sadly missing the catboat’s return to the family’s dock. 

After 25 years, Ms. Robertson is about to hang up her proverbial captain’s cap after the Island-bound sail, but it’s not the end of her family’s story with the Selina II. Instead, it’s the opportunity to begin a new chapter.

A LIVING PIECE OF MARITIME HISTORY

“Anybody who knows catboats ‘oohs’ and ‘ahhs’,” Ms. Robertson said of the grand single-masted vessel. Indeed, the boat is the only surviving example of a catboat over 40-feet long (only four were ever built), making it a bit of a special spectacle to sailing fans and aficionados.

As Ms. Robertson tells the story, her grandparents “wanted a boat and they got a long, skinny power boat. It was tippy and it made my grandmother nervous.” The family got rid of that vessel, the Selina I (“Selina” being a family name passed down through the generations), and had a second boat, Selina II, built in the H.W. Sweet Shipyard, now known as Clarke’s Shipyard at the end of Carpenter Street in Greenport — “a knockoff of a Crosby-designed catboat in the Massachusetts area but bigger,” she explained.

A catboat is a traditional sailboat with a single sail on a single mast set forward in the bow. According to the Catboat Association, “A commonality of catboat design is a beam of one-half waterline length, making them very stable and comfortable boats. Cruising catboats have cabins and normally range in overall length from 16 to 26 feet.”

Ubiquitous along the New England coast down to Chesapeake Bay in the mid-19th and early 20th centuries, catboats were used inshore by fishermen harvesting finfish, lobster or clams, or for transportation, racing or as pleasure boats, their use only declining as the rise of engine-driven vessels grew.

“My grandfather,” Ms. Robertson said, “was her master from 1926 to 1962 — 36 years, not to be outdone by his daughter, Mildred Esther Hird Hunt, master from 1962 to 2001 — 39 years.” And Ms. Robertson took over the helm of the Selina II in 2001.

I asked my father, ‘How much do you spend every year to maintain the boat? Does she come with an endowment?’ He shrieked with laughter!” Ms. Robertson recalls with a smile. But the question was prudent: maintenance costs on a vintage wooden vessel can easily reach five or even six figures, not counting docking and servicing fees. 

“I did what many before me did, hang a shingle and [offer] sailboat rides,” she said — and she did exactly that, providing historic sailing tours on Chesapeake Bay through her business, St. Michaels Sailing Charters, for a quarter century. “I had a lot of fun, but after 25 years and 60,000 passengers it’s time for me to retire.”

But this is not the final family sail on the Selina II. The vessel now passes to Robertson’s niece Selina Truelove and Truelove’s husband, Jeff, of Greenport. In their search for a new captain, they struck gold in the form of Luna Pearl Crowley — a sailor who grew up spending summers on Shelter Island and who happens to be the great-granddaughter of legendary shark hunter Frank Mundus.

SHELTER ISLAND MERMAID

Ms. Crowley, 27, and her siblings grew up spending summers on Shelter Island, as did their parents, Steven and Lisa, who’ve been visiting the island since they were teenagers. The family lived in Massachusetts but had lots of family on the East End, and she became especially close with her great-aunt Pat Mundus, one of the first female cadets to graduate from SUNY Maritime College and who traveled the world working as a ship’s deck officer on oil tankers.

“My Aunt Pat calls me ‘Mermaid,’” Ms. Crowley said, “that’s her nickname for me. I grew up jumping off the boat, snorkeling, swimming … I had my sea legs, but I didn’t know the knots or the rules of the road or any of the practical captaining stuff.” 

After she graduated high school in 2016, she took a gap year to go on a sailing adventure with her Aunt Pat for nine months, beginning her maritime education.

 “That’s where I learned how to sail, on [Mundus’s boat] the Surprise” she said,  a 57-foot wooden Spaulding Dunbar ketch that Mundus and her husband, Earl, spent three years restoring.

After a month of maintenance work done by Ms. Mundus and Ms. Crowley sanding the ketch by hand in Clarke’s Shipyard, the duo sailed from Greenport down the coast, veering into the Hudson River so that Crowley could have the experience of sailing in New York City. They then sailed south to Cuba and spent a couple months in the Bahamas. Ms. Crowley learned to tie knots, to spearfish using a Hawaiian sling, to navigate, to deal with the current and the wind. 

 “That trip changed my life,” she said. “Sailing just by nature teaches you self-responsibility and honesty and communication and resilience.”

It was a coming-of-age trip for the budding sailor, one that helped her grow and find a path. “I was a little bit of a rebellious kid … I was signing up for the adventure because it sounded awesome, but it really made me grow up.” 

The pair became close as Ms. Crowley gained experience and knowledge. “I needed to learn how to do set and drift so I can know where we are when we’re doing an offshore passage,” she said. “I needed to know how to communicate effectively with my Aunt Pat when she’s at the helm and I’m at the bow of the boat so that we can set an anchor and not damage the boat or pull up to a dock.”

Ms. Crowley learned more than the tenets of sailing from Ms. Mundus, who became her mentor. She learned about responsibility and communicating clearly but kindly, about how to do things the right way and why. 

“My Aunt Pat is my second mother … she continues to be the person I go to talk to about things that I don’t want to talk to my parents about. She’s such a wealth of information and life experience, and I look up to her so much,” said Ms. Crowley. “We really developed such a beautiful, deep bond throughout the years … and I’ve been told that I’m just like her, too, so it makes sense that we get along so well.”

After the sailing trip, Ms. Mundus told Ms. Crowley she would split the cost of the captain’s course with her if she wanted to get her captain’s license. Ms. Crowley worked at a café to save up her portion and took the week-and-a-half-long course in Massachusetts, the youngest person in the class and one of only two women attendees. With encouragement from her mother and Ms. Mundus, she obtained her license in 2017 at 19 years old. 

SAILING AND SERENDIPITY

Ms. Crowley went on to study neuroscience and worked as a researcher at Johns Hopkins University in Baltimore, attaining a master’s degree in psychoactive pharmacology and beginning another to become a licensed therapist, until the opportunity presented itself to take over the charter business with the Selina II. 

“I’ve always done captaining as a way to support my education,” Ms. Crowley said. “I was captaining in Baltimore last summer, the first summer away from the East End, and I told my best friend, ‘I’m going to captain in Long Island.’” 

Two days later she received a message connecting her with Jeff Truelove, who was looking for a captain. 

“It was an extraordinary fit,” said Ms.  Robertson. “Her name is Luna Pearl … ‘Selina’ means ‘goddess of the moon’ and ‘Luna,’ of course, means ‘moon.’ My niece [is named] Selina Marjorie — seven generations have the name ‘Selina’ — and Marjorie means ‘pearl.’ It’s more than a coincidence.” 

Ms. Robertson says the Shelter Islanders who remember the Selina II are excited to have her back. “I ran into Stuart Nichols, [the Selina II’s] mechanic. He was gobsmacked and is so excited to see the boat again,” she said. “Bob Mills at the canvas shop in Greenport [Wm. J. Mills & Co.] said he was excited she is coming back and offered to help with whatever we need.”

A NEW CHARTER CHAPTER

As the Selina II is staying in the family, it’s also staying female-driven. Ms. Crowley, who is leasing the boat from the Trueloves, has hired mate Haley Mae Mason and created a website for her new charter business, which will run trips out of Dering Harbor and is licensed to take six passengers.

Her New York return kicked off with the Blessing of the Boats in Greenport, an old tradition where clergy offer prayers for safe travels of boats, their captains and passengers. On a beautiful Saturday in June, her mast aflutter with nautical flags, the Selina II bobbed in the harbor in all her 100-year-old glory, attracting the appreciative gaze of onlookers from shore.

“We’re doing things like sunset charters and full-moon charters — I became an ordained minister so I can marry people on the boat,” Ms. Crowley said.. “I was talking to Jeff Truelove and his wife, Selina, about different fun ideas that we could do, like a birding cruise where we have a naturalist on board.” 

Ms. Crowley’s services will be offered to guests of The Chequit, the historic hotel within walking distance to the town dock where Selina II is anchored, just across the harbor from where her life began. “It’s great because The Chequit was built in 1872 and this boat was built in 1926. They’re both historical Shelter Island pieces — the boat and the hotel feel like a match made in heaven,” Ms. Crowley said. “This is such a unique place, a unique boat. I have such gratitude for the family for taking me under their wing. I have so much gratitude for all of the women captain mentors that I’ve had in my life … for just having that community, and then one day passing that on.”