Becoming Pirate Mama: Rethinking Life As a Single Mom

Ky Delaney


The wind blows fierce at 25 knots, strong enough for a Coast Guard small craft advisory. We’re heading straight into the wind so we must tack the boat, zig-zagging in our race against the sunset to reach Salt Island, one of the southern British Virgin Islands.

I’m chartering a 34-foot sailboat, the Kaz, for a month with my four-year old, Tobin, and my friend, Sarah, who is crewing for me.

I flirt with the edge, inching the boat as close upwind as it will steer and the boat keels over sideways.

Tobin scurries down toward our cabin, slipping on the steep steps.

He lands with a loud thud.

I’m okay,” he yells before I can ask, getting up and running toward the bow where the boat narrows, cradling him.

I try to believe him, but doubt creeps its way in side my thoughts, settling on my shoulders as I gaze out at the horizon, white peaks breaking atop sapphire mounds. Today is Tobin’s first time sailing. Watching his small body pitch back and forth as the hull of the boat is perched at shocking angles to the sea racing below unnerves me. While I’ve sailed before, I’ve never been the one in charge.

Just when I’m sure I’ve gotten in over my head, I remember Anne Bonny, a strong, independent woman who became a pirate in the 1700s. While other Victorian women were kept indoors with limited freedom, Anne sailed the Caribbean where she earned a reputation as fierce and capable. Dressed in male attire, she fought, drank, and swore alongside men. Anne inspired me to learn how to sail a boat on my own.


Last December in the mountains of North Carolina, sailing in the British Virgin Islands was the furthest thing from my mind. Grey settled like a wool blanket that refused to budge when day care called, and told me that Tobin threw up. On the way home, we stopped for flu basics – Gatorade, saltines – and milk for my coffee: the one thing that got me out of bed every morning.

In the dairy section, Tobin insisted on getting the milk himself and picked up a gallon of chocolate. As I redirected him toward the two percent white milk, a woman with a pixie cut called out to me.

“Ky, right?” Then looking down at Tobin she tapped the side of her head. “And don’t tell me. His name will come to me. Um…”

“Tobin, his name is Tobin,” I said, stalling in the hope that I would remember her name, realising I must know her from day care.

She extended her hand. “I’m Maya, mom to Finn, Ollie, and Callie.”

“Three, wow,” I said. “I can barely manage one.”

In the time I had been talking to Maya, Tobin added three gallons of chocolate milk beside the jug of two percent.

She laughed. “I have them half the time, so that helps.”

“I’m a single mom too,” I said.

Her face froze and I knew I said something wrong, maybe I was too enthusiastic, maybe calling someone a single mom, even by implication, was some type of slight.

“Er, um, I’m a co-parenter, maybe that’s a better way of putting it,” I said, trying to make amends – although I wasn’t entirely sure for what.

Her face softened. “I like that better. A single mom seems like you’re doing it all alone, but you’re not, are you?”

I paused, wanting to sound upbeat and still communicate the loneliness, the gaps, the hardness of it.

Before I said anything, Tobin looked up and asked, “Mama, you’re a single mom, mama? What’s a single mom?”

He was crawling on the underside of the cart, his belly flat on the rack meant for groceries too big to fit in side, his hands hanging between the hind wheels, his fingers prodding their diameter.

Two women walked by and one gestured toward Tobin. “I once saw a boy lose a finger that way, the cart ran right over it and there was blood, blood everywhere.”


I feel the strong gust on my face and ears first, then see it dance on the water. Before I can call out to Sarah to let out the sail, the wind leans us further.

The lifelines skim the water’s surface.

The sailboat is so tilted that I can no longer stand on the floor.

A stack of plates falls on the floor and breaks.

Twenty gallons of water slam from one side of the cabin to the other.

Two bags of garbage fall over, sending remnants from our last few meals all over the boat.

Tobin screams.

I want to go down and hold him, but right now I’m straining every muscle in my body to hold the boat into the wind. I tell myself that he’s okay in our berth, soothing himself by playing with his seaplane.

I block out Tobin’s crying and think about what Anne Bonny would do. In her teens, she beat up a man who attempted to sexually assault her. As a young woman, she refused to marry the man her father chose for her. When her marriage didn’t work, she left her husband and became a pirate. When the British Navy boarded the pirate ship Anne sailed on, she fought them off while her male counterparts hid below deck.

I stand up taller, pinning my shoulders back, feeling more determined, more like Anne Bonny.


The day after the grocery store incident, Tobin alternated between shivering and sweating. I cuddled him and soaked him in a cool bath, all the while wondering if I really was a single mom.

Tobin’s dad took him every other weekend, picked him up after day care once a week, and sent me a check for half of his expenses each month. Even with this help, I was parenting alone most of the time.

As a lawyer, my instinct was to look up the phrase ‘single mom’ in Black’s Law Dictionary. Nothing.

I turned to medical dictionaries, craving a word, a definition, to belong to a tribe who knew my struggles as their own. I craved an identity.

The closest I came was ‘single-parent family: a lone parent and offspring living together as a family unit.’

By that definition, Tobin and I were a single-parent family; so were Tobin and his dad on the two weekends a month when he was there.

Then there was the reference in Urban Dictionary, refreshingly unapologetic, undeterred by political correctness. It included a quote from the actor and comedian John Leguizamo: “basically, a polite way of saying: broke, exhausted, and nobody wants to date your ass.”


Tobin recovered from the flu and returned to day care, but I wasn’t so lucky. I caught Tobin’s flu and when it evolved into mono, I felt stuck not only in bed, but also in my life, trying to balance a legal career with raising Tobin. Yearning for an escape, I ordered books about sailing, recalling my college days when my sweetie and I lived on a sailboat and dreamt of one day taking the children we’d have sailing.

One of the books contained pirate stories and I became intrigued. Instead of the plunderers and rapists I had envisioned, as many as 40% of the crew on a pirate ship were liberated slaves. Crews represented remarkable diversity and piracy embraced multicultural attitudes long before western nations.

The gold-hoop wearing, peg-legged seafarers captured my imagination, not because of their brutality, but because of the clever ways they organized themselves outside the reach of government and society. Pirates readily accepted misfits, welcoming outcasts into the fold as kindred spirits.

In so many ways, I felt like a misfit. Whenever I read about single moms, I recognized aspects of myself, but I didn’t fit in with the teenage single-moms. Neither did my story resemble the single moms closer in age, the women who looked their ticking time clocks squarely in the face and deliberately took steps toward motherhood.


I returned to work as soon as I recovered. I began to rush through the evening routine, the highlight of my day when Tobin fell asleep and I retreated into bed to read about Anne Bonny.

Born in Ireland, her father raised Anne and dressed her as a boy and called her ‘Andy.’ Anne’s mother died when she was twelve and then Anne and her dad moved to Charleston, South Carolina. There, Anne managed the household while her dad became a merchant businessman.

Anne refused to marry the man her father chose for her. Instead, she married a poor pirate and moved to the Bahamas, where her husband, James, became an informant for the governor.

She mingled with pirates at bars where she met the pirate John ‘Calico Jack’ Rackham; the two had an affair, and had a child together.

James dragged Anne before the governor, and Calico Jack offered to buy her in a divorce-by-purchase. Anne refused to be ‘bought and sold like cattle.’ Instead, she and Rackham stole a ship while it was anchored in the Nassau harbour, and escaped to become pirates. Anne became known for her violent temper and ferocious fighting, earning the nickname ‘fierce hell cat.’

In October 1720, when their pirate ship was anchored off of Jamaica while they celebrated capturing a Spanish commercial ship, a British Navy sloop surprised them. Anne’s drunk male counterparts headed below deck, but Anne stayed and fought back, holding the British Navy off for a while.

After the entire crew was captured, they stood trial. Some of the crewmembers testified against Anne, stating that she encouraged them to greater acts of bloodshed and violence. They were all sentenced to death by hanging. Anne was pregnant and pleaded her belly. In accordance with English common law, she received a temporary stay of execution until birth of the child. Her last words to Calico Jack were that she was ‘sorry to see him there, but if he had fought like a man, he need not have been hang’d like a dog.’

Anne disappeared from the record. No historian knows for sure if she was released, executed or escaped. My favorite theory is that Anne escaped from jail, gave birth at sea, and sailed to the Caribbean with her infant.

I wondered why I hadn’t heard stories like hers about single moms, ones that show our heroic strain. Somewhere deep in side a glimmer of possibility stirred where before I’d only felt despair. I imagined the adventures Tobin and I could experience, and for the first time in a long while, I allowed myself to daydream about creating a bold, watery life for Tobin and me. A month later, I enrolled in sailing classes in Anne’s hometown of Charleston, South Carolina.


For the next two hours, we sail up the Sir Francis Drake Channel. The sound of wind filling canvas and the lines rattling loose against the mast let me know whether to let the sails out or to sheet them in tight.

The line in the distance, where the sky blue meets its liquid mirror, mesmerizes me. It’s just the wind and swell, Sarah and I sailing, and Tobin napping below deck, when a series of brown-grey humps smudge the horizon.

If I squint, I see the masts of sailboats bobbing in the sound. With each tack, Salt Island becomes closer. We can make out the craggy cliffs bordering the harbour, and then the crescent of white sand beach lined with palm trees.

We round the point to anchor at the northern most side of Salt Island. In side the harbour, the wind subsides. The water flattens, the deep blue turning into turquoise, the late afternoon light hitting the water’s surface at the perfect angle. The water glows.

The floor returns to under my feet.

The world rights itself.

Tobin climbs up the companionway. My heart swells with the sight of his smile.  He stands by my leg, holding onto the steering wheel.

He points. “Turtle!”

I squeeze him, soaking up the abundance of getting to be his mama and be with him here, on the sea.


The last Sunday afternoon of our sailing trip we sit at an outdoor bar on a beach fringed with palm trees, admiring the way the water laps against the white sand beaches. This particular harbour is far enough away to be outside the typical cruising route for sailors on a week-long vacation.

I drink a Bushwhacker, a frozen, white, alcohol milkshake consisting of a few thousand calories, while Sarah drinks three Coors Lites, and Tobin digs in the sand.

A middle-aged guy wearing board shorts and a black t-shirt with a skull-and-cross-bones flag pauses at our table and asks if we drove here from the ferry dock.

“No, we sailed here.” Sarah extends her hand. “I’m Sarah – and what’s your name?”

“Fred and no kidding, this is a bit off the beaten path.” He pulls up a plastic seat and joins us at the table.

“We’re sailing for a month so we’ve covered a lot of ground,” Sarah says.

Tobin runs over and climbs onto my chair. I push my Bushwacker further back on the table to prevent Tobin from spilling it.

“But no, who really sails the boat?” Fred asks.

“We do,” Sarah says.

Fred looks confused as he studies us, Sarah in her bikini top and cut-off shorts, me in a form-fitting purple sundress.

“Where is your captain? Did he take the afternoon off?” he asks.

“She’s our captain.” Sarah gestures her thumb toward me, now deep in conversation with Tobin trying to answer his question of whether a sea turtle or manta ray would win a swimming race.

Fred stares at Tobin in my arms.  He scans every inch of me, from my greasy hair tucked under a trucker’s hat to my salt-stained dress. Under his gaze, my skin tightens and I realise that fresh water hasn’t touched my skin in weeks.

“You’re the captain?” His tone full of shock, his expression says now he really has heard it all.

Tobin nuzzles his nose against mine and widens his eyes at me. “Arggghhh. My mama, pirate mama.”

I laugh and with perfect clarity, conjure an image of Anne Bonny. Her red hair worn long under a three-cornered hat, a billowy shirt still over dark pants, she wields a pistol in one hand and a sword in the other. Anne became one of the best-known pirates even though she never commanded a ship of her own.

Fred quizzes me about the height of the mast, the engine’s horsepower, and how many tons the boat is.

I shrug, not knowing.

I start to tell him about what matters, how my life has been reduced to gradations of blue. That Tobin jumping off the stern into the shimmering aqua water with his arms spread wide-open makes me burst in side. Or how I dance in the silvery-blue light the moon casts across the bow. I think of the intimacy I’ve gained with the sea, that I can recognize the siren call of the palest blue, how it lures the uninitiated sailor closer into the shallow depths. A few shades darker turquoise offers a safe anchorage on a sandy bottom. I’ve learned the moody blue of an agitated ocean means it’s time to reef the mainsail, and can tell the magnitude of a squall by the darkness of the blue-grey army of clouds marching across the sky.

His eyes glass over a bit.

I gaze across the harbour at the Kaz, anchored and moving in rhythm with the gentle swell. Tobin wiggles in my lap when out of the corner of my eye, and I swear I see Anne Bonny raising her Bushwacker to mine, toasting our journey. I hear a whisper on the breeze and know that she’s proud of me, a mama captaining a boat.

Ky Delaney

is a

Contributor for Panorama.


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