I am in flight in Black River, Jamaica—giving my Jewish traveling companions the slip in search of a driver curiously named Dragon to make it to Mahogany Hill. I stand out in all whites like a cricketer, wearing a button-down and pressed slacks, but my footsteps are subtle enough not to draw attention.

Here I am at 28 in Dezna’s native land, searching for my nanny’s essence, her origin. Language—as a writer, a human being—has best defined who I am, and Dezna is a part of me in that respect. My oral delivery, after all, comes with an imitative exponent: her Jamaican lilt with hollowed-out vowels and consonants as crisp on the teeth as watercress. What had been performative in my childhood has become ingrained, and since Dezna’s death five years before, I have tried to find the root of her strong voice to understand my own. But travelling to Jamaica specifically on a pilgrimage to discover my nanny’s history would seem a blunt betrayal of my parents’ love, not to mention as gratuitously unkosher as a bacon double cheeseburger. So I deluded even my rude bwoy self and concocted a decoy: I signed up for an exploratory mission to document Jamaica’s Jewish cemeteries, some of which have a spooky pirate past.

During this undertaking, the putative reason for my trip to Jamaica, I embedded with a group from the nonprofit Caribbean Volunteer Expeditions to survey these forlorn graveyards and investigate the Jewmaican Pirates of the Caribbean. At the very least, went my flawed logic, I’d have some opportunity to find shared terrain with my nanny: here was a shoal connecting the two shores of myself, the Jewish and the Jamaican. But something about that prefab strategy didn’t feel right. It was a compromise. And that’s why I had to reject this clinical glance at life here and find an authentic connection to Dezna by heeding Winston’s words. As she used to say, “The ‘art wants what the ‘art wants…,” her accent blending the sentimental and aesthetic. And that set in motion my covert communiqué with her oldest daughter, Maxine, and the enlistment of Dragon as chauffeur. Of course, I might draw a tongue-lashing from the crew for shirking my duties, but I was after a different kind of secret hidden in the heart of the Caribbean. It would be easier to beg for forgiveness than ask permission.

Suddenly on this sleepy Black River side street, someone calls out to me in a deep bass, startling me just as I’m slinking into my role as guided-tour defector.

“Ross—Rosstaman! Wah gwaan, mi yute?”

It’s Dragon, a short, middle-aged fellow standing outside a dirt-splattered van parked by the Anglican Parish Church with its mullioned windows. A bald guy in dungarees and a shortsleeved plaid button-down, he’s peering at me from over the thin-lensed sunglasses perched on the tip of his nose. He just emanates cool. Stick him in a suit, and he might easily star in a Ciroc ad.

Wah gwaan?" I say in greeting. His hand is rough as a longshoreman’s when I shake it, and I give him a fraternal pat on his bicep. Dragon is just five-two, but he’s built as can be from all the construction work he does. There’s a whole story, it is said, to how he acquired his moniker, about which the less said, the better.

Maxine and her friend Nadia are in the back seat, and they slide open the door and step out so we can all exchange a tight embrace.

“Mannas, mi bredda,” Maxine says as her own hello. Leave it to Dezna’s daughter, who considers me her brother as I do her my sister, to greet me with the slang word derived from “manners”—the implication being it’s polite to offer a hearty salutation. Dezna was, after all, a stickler for rules.

Max is 47, about the age Dezna was when she came to the States, and has a mother hen disposition. Her hugs are all bosom—her posture bent forward. She clucks any disapproval with a suck of her teeth. In fact, her nickname is Beez, given her queen bee demeanor.

We pile back in the van, and I hop in shotgun.

The choreography of this exodus resembles a coordinated heist—the careful treading, the hushed voices. Then there comes the simple instruction for Dragon: Step on it.

But the car stalls just as the Jewish volunteer group I’ve escaped turns the corner and approaches from down the street. If the leaders catch me, I’ll be guilted into more cemetery fieldwork and have to forgo this side excursion. I suppose I could have simply informed them of my plans, but that would have been a little less exciting.

Max’s hair is tied back to allow puzzled disapproval to appear more easily in wrinkles on her forehead. She also speaks almost exclusively in aphorisms, and when Dragon can’t get the car started after a couple tries, she starts her lamentation.

“If it’s not the button, it’s the buttonhole,” she sighs. “A dat mi know fi true.” Jamaica doesn’t always adhere to the “no problem, mon” script resort brochures provide, the very story Dezna sold me through omission during my childhood. Instead, there’s this one guarantee: If it’s not one thing, it’s another. Maxine knows this all too well and rolls her eyes as if to say, “I can’t even.”

Dragon shuts the vehicle down and vigorously turns the keys in the ignition—this time with success. He shoots me a side-eye of satisfaction.

“Ah suh we dweet,” he says, his voice a hickory synth. That’s how we do it.

Now it’s time to bus’.

Under the cloak of shade in an alleyway—the stuccoed homes stretch tall to catch whatever breeze possible in this baking Jamrock January—we beat a path inland toward the hills where the pumpernickel-colored soil is loamy. There it will be possible to find Dezna’s origins, her childhood homestead.

Travel Guide to St. Elizabeth, Jamaica

Even those who are North Coast devotees can explore their more adventurous side by branching out to St. Elizabeth parish, this lesser-traveled-by part of the island and Dezna’s home turf. In Another Mother, I explore the history and the beauty of this hidden treasure in southwest Jamaica, and if travelers feel inspired to visit, here are my five go-tos in this over-the-beaten-path paradise.

For those who need help getting around, Dezna’s family runs Coco’s Tours Jamaica, a tour transportation company that provides custom itineraries for travelers, with particular expertise in St. Elizabeth.

YS Falls—A beautiful series of seven cascades, this natural wonder is the perfect place to beat the heat on the island. A short drive from Black River through Holland Bamboo, a magical tunnel created from curved bamboo on either side of a road, these waterfalls sit among vast pineapple groves. Visitors can swim in the gorgeous pools below and zipline across the falls.

Lovers’ Leap—Part of Jamaican lore, the kind Dezna and her family recounted during storytelling evenings, this is the spot where two eighteen-century lovers are said to have jumped to their deaths rather than live apart. This cliff, with a 1,700-foot drop off into Cutlass Bay, provides one of the most dramatic vistas in all Jamaica. Recently, Jason Henzell, son of famed Jamaican filmmaker Perry Henzell, turned the building on the property into a hip spot to enjoy live music while eating oxtail, sipping a Red Stripe, and taking in the view.

Floyd’s Pelican Bar—Make all of your Instagram followers jealous with a trip to this thatched-roof bar on stilts, situated a mile offshore. A picturesque watering hole amid azure waters, Floyd’s Pelican Bar serves strong rum punch and fresh seafood. Of course, you’ll need to take a boat to get there, but it’s well worth the journey. Prepare to get unfollowed.

Jakes Hotel—A funky, sophisticated resort in Treasure Beach, Jakes has colorful villas, oceanfront bungalows, and more traditional hotel rooms that incorporate the simple natural beauty of the island with Jamaica’s signature outlandishness. It’s also the site of the Calabash International Literary Festival.

Black River—Black River, the town featured in this excerpt and the capital of St. Elizabeth, is a vibrant place with gorgeous architecture, particularly the Georgian and Victorian buildings. Visitors may enjoy a water safari tour on the famed Black River itself. It’s a town I like to wander through before settling at a rum shack to rest my legs.

Ross Kenneth Urken is an American journalist who has written for The Washington Post, The New York Times, The Paris Review, The Atlantic, VICE, Tablet, National Geographic, New York, Esquire, The Wall Street Journal, Bloomberg Businessweek, Sports Illustrated, ESPN, The New Republic, Scientific American, the BBC, The Guardian, and Travel + Leisure. A graduate of Princeton University, he lives in Manhattan with his wife.