Realizing My Grandfather’s Sailing Dreams

When Covid hit, we already had the boat, so we only had to throw the lines

Dennis Meene/Flickr
Dennis Meene/Flickr

When you dream of sailing into the sunset, the best place to start is not the Internet. There you’ll find clear teal water, rolling waves—the edited versions of other people’s dreams. Instead, walk down the farthest dock at any marina and find the boats that were once loved: varnish peeling, decks soft. Watch the algae flowing off their keels. Find that very back part of a boatyard where boats go to die and the grass grows up around them and their insides are gutted. And know that they all once had a name.

For years, my husband, Josh, and I watched the sailing videos on YouTube, with their clear teal water and their rolling waves. One video in particular we watched so many times that I could imagine it without actually viewing it. Listening to the words and the music in the car, at work, in bed, I could see the color of the sun on wood, soapsuds on the deck, a saltwater shower. This eight-minute documentary was a visual representation of our dream. Combined with years of striving to be unlike everyone else, it was our way in. A spark. A way to live.

That’s how we ended up buying Ling Ling. She was out of the water—“on the hard”—when we went on a hot August day in 2015 to see her at a boatyard in Deltaville, Virginia: a 44-foot 1979 Kelly Peterson sailboat built for the open ocean that could take us around the world if we let her. We climbed, delicately, 15 feet up the ladder, and looked, stooping down into her cabin, while the broker told us, “She’s a real piece of work.”

“She can hear you,” I said for the first of many times over many years, knocking on her inlaid teak table, her wooden cabinets, and her bookshelves that change to that golden hue in sunlight. Later, we would climb up that ladder from the gravel to the deck, as easily as you would walk through your house in the middle of the night with lights off to get a glass of water. We’d climb as though we were on flat ground with buckets in our hands, jigsaws and epoxy, rolls of fiberglass, and plastic bags with 7-11 lunch, and we’d sit on the slabs of cardboard covering up the cockpit wood and take a break.

When we were dating, Josh and I spent a weekend away at Assateague, where we canoed against 20 knots of wind, only to realize that the water was so shallow we could walk in it, and so Josh did, pulling the canoe with a rope tied to his waist. That’s where the dream began. We sat in knee-deep water, found mussels in the sand, and we dreamed of clear blue water, of sailboats. Of heading south.

When we found ourselves in an old farmhouse on Church Lane in Hampton, Virginia, after years of D.C. city life, the dream became more pressing. We would buy a boat, fix it up, quit our jobs, and sail south to the Caribbean. Commuter traffic exacerbated the urgency. The dream was on, the dream was off—too expensive or too outlandish, until one day I sat in particularly bad traffic on my way to work, and I had time to do some thinking about how this wasn’t what I wanted for my life. I called Josh: “What if we lived on the boat?” To which he said, “The last time I lived on a boat, it wasn’t fun.” I convinced him that a sailboat wasn’t exactly an aircraft carrier, and that this way we could save money for our big trip.

Our boat would become a beautiful bond between us, and not just out on the water. The first year we owned her, she was on stilts, as we re-did every last part of her, down to the epoxy in her keel. Every Saturday, I would drive to the boatyard, past the bend in the road that floods at high tide, to the smell of marsh grass and paint. The only other car parked next to all the boats-on-stilts would be Josh’s, his dinged-up silver Mazda 3, its entire back seat a tool shelf that rumbled over speed bumps. Seeing his car and the ladder already up against the hull, I’d allow myself a little smile. And there he would be with his bandana tied around his head, holding a blowtorch to the rudder to straighten it out, whistling something always.

“Good morning, dove,” he would say.

Sometimes we’d sit there on the bow at sunset, our bodies aching, and say, “These will be the best days of our lives.” The worst, I’ll give you, but also the best. The sound of a Popsicle stick mixing epoxy in a paint cup, the fulfilling slice of a jigsaw through vinyl, and the sudden release of wood when it separates from the blade—these all make me nostalgic for the discomfort of that time. For kneepads on the deck, crouched over, as we sliced out the rotten wood. We made a two-person assembly line, often at night—because once you start fiberglassing, you can’t stop—layer after layer cutting the glass sheets, dabbing, cutting, dabbing, under a yellow light plugged into an extension cord. We would throw the wadded-up acetone paper towels and Popsicle sticks over the side of the boat onto the ground. Every night, we would collect the trash in a bucket and take the ladder back down again.

Around that time, in the worst part of the overhaul—when our benches were tool shelves and there was a thin layer of fiberglass dust over every surface, and everything was taking longer than we thought it would—my mother gave me a scrapbook that she’d made about my grandfather’s own sailboat adventures. It was a photo album, the binding decorated with nautical charts of exotic places, aptly titled in my mother’s blue, teenage cursive, “The Dream.”

The inscription reads, “To Daddy, for your birthday and the first sail on your boat. Nov. ’72 Love, Annie.”

My grandfather built a trimaran in his back yard—31 feet, three hulls, a cutter rig made of plywood with a thin coat of fiberglass to seal it in. I never met my Grandpa Jack; he died before I was born. But I had heard the stories of his boat, which had become family folklore: the time my mom, uncle, and grandfather had sailed through a lightning storm and beached it to clean the bottom and how he launched it for the first time right behind the house and into the Ortega River, where my mother would sail her own tiny sloop after school. It had always been his dream to build a boat and sail it to the Caribbean, and he sure as hell built the boat.

Until we bought Ling Ling, I hadn’t grasped what it meant to build a boat from scratch. We had planned out our own rehab, how long everything would take, how much it would cost, how much our bodies would or wouldn’t hurt, and we were wrong about all of it. But so, as it turned out, was my grandpa.

Within the thick browned pages of his scrapbook, I found beautiful tokens of advice from a man who had never known I would come to be. The local newspaper had written a story about him—the 1971 Jacksonville Times Union and Journal—and here it was, taped and ripping gently at the fold: “Dreaming of Island Sunsets? It Starts in Your Backyard.”

“His advice to other would-be boat builders,” the article reads, “is don’t let the time element assume too great an importance.”

“Have a deadline? Yes, but I’m not meeting it,” he said. It was as if he was talking directly to me. I cherished the pages, studied the yellowed photos and my mother’s writing in the margins. “One step at a time. It’ll drive you nuts otherwise.”

It took years longer than he thought, but my Grandpa Jack finally finished his boat. And so, we would finish ours.

We knew all along that Ling Ling would be a project. She needed a new deck. Okay, easy, we’ll re-core it. She needed a new ceiling—easy. A new paint job, top and bottom. New cushions. A new stove. New bed. New hatches. New a lot of things. And things that we didn’t know she would need, she did need. The broker had tried to warn us. We saw her teak, the little cabinets that you stick your fingers through to pull a lever, the wooden rung in the closet, the intricate decorative shelves in the v-berth that would hold our books and our blankets, the angled walls a built-in nest. We saw the way the ceiling in the aft cabin hung out over the bed, making a little nook, the wooden ladders up into the cockpit, the sliding companionway hatch, our perfect fort.

“She’s going to be a lot of work,” the broker said. But Ling Ling, she was perfect.

At first, we thought we’d name her Miss Adventure. But at closing, the name she’d had for 36 years took hold of us, too. Ling Ling’s name, “very beautiful” in Mandarin, had never been changed. You quickly learn that sailors are superstitious, and I come from a long line of them. When I was right out of college, I wrote a short little article for the Scholar, where I was an intern, about an artist named Debra Howard, who lived and traveled on her boat, then docked at Tangier Island. She was an artist-in-residence hired by the island’s art museum to document an Old English–speaking colony’s last remnants, slowly eroding into the Chesapeake Bay, as the people lost their accents to children on the mainland and the men collected oysters and crabs in the early hours of the morning. I interviewed Howard on the phone; she told me about her artist studio in the v-berth, about the island people and why she wanted to preserve their way of life. Her paintings were raw and colorful, a painterly gist, an impression.

At closing, when Josh met the owner of the boat and they somehow started talking about Tangier Island and somehow he mentioned my article and somehow she realized, “That was me!” we had the beautiful realization that Ling Ling, had been Debra’s home for 28 years, that the v-berth, where I’m writing this now, sitting on cushions that I made, against walls that I carpeted, under a ceiling that taught me to use power tools—this was her studio. There had once been paintbrushes in my underwear drawer, oil stains on the plywood, her dogs’ hair in the bilge. She had raised a daughter on the boat, sailed it up and down the coast from the Bahamas to Maine, hauled out the engine with the weight of the boom.

We would spend years slowly peeling back her work, uncovering her patches, discovering the many little things that make a home a home that do not involve walls or furniture or solid ground—but Ling Ling she will always be.

Eventually we got her in the water, but it was years more before we got to enjoy sailing her. We lived on the dock like ordinary people, going to work each day, then coming home to a floating endless live-in renovation project in a setting of serene natural beauty. It was years before we got to enjoy the nice, long rolling swells and a steady 12-knot breeze, when I would stand on the swim ladder behind the boat, facing backward, with my arms spread out across the stern. With my heels under the water, I was level with the horizon, bobbing up and down with Ling Ling, with all that water pushing and pulling around us, and there I was, just part of it. I’d let go for a second to feel the rush, but just for a second, and Josh would scold me for yelling (how can you not yell with the freedom of it, like being naked on top of a mountain?) since he was nervous that, one day, I would let go for too long.

We watched our retired neighbors head south to avoid the Virginia winter—not cold enough to freeze, most of the time, but cloudy and dark and brisk enough to require fleeces and blankets and wind-proof coats to walk the occasionally icy docks. It is not what you picture when you move onto a boat. In November, the sailboats were all pointed south, with their water-makers and bicycles, and dinghies dangling off the deck. On Saturdays, we would sail along with them to the point where the Chesapeake Bay meets the Atlantic Ocean, that arbitrary line between two waterways, then drop the sails and motor back in, to normal life, to the dock, to jobs and cars and gym memberships. We had our own plans to head south, first one year, then the next. But Ling Ling did not feel the same sense of urgency.

Our deadline pushed back, then further back, and it was all more expensive than we thought it would be. Ling Ling needed a new motor. She needed new sails, new rigging. She needed a new enclosure. I started to question whether it was worth all of this. What happens when we go on a six-month trip that we’ve built our lives around and then the six months is up? Then, will we be satisfied?

It wasn’t until Covid hit and we were no longer required to live in Hampton for our jobs, that we began to see an opening in the fold of what our future could hold. Our friends joked that we were ready, waiting for this to happen. We already had the boat; we had only to throw the lines.

As we waited for the world to start back up again—two weeks, a month, a year—we went from spending most of our days in offices, cars, and airplanes to spending all of our time in the boat—together. Josh’s office and my office were, all of a sudden, 10 feet apart with no doors or walls or windows or big concrete barriers that might have done the trick to drown out the sound of someone who thinks that he cannot be heard on a video call unless he is shouting.

He craved social interaction, and the engineers he worked with would have “social lunches” with their cameras off. I, on the other hand, would eventually start declaring “girl’s nights”—singular girl—so that I could be alone in the boat with wine, Nutella, and television.

But with all the adjustment, there was a calm that had settled over us; there was a calm in all this. My alarm shifted from 6:30 to 8:00, and I did yoga on the deck at midnight. Sometimes, I would have dance parties out there all alone, starting off slowly and then letting it all go. I planted an herb garden. Josh’s schedule naturally moved earlier, and he was surprised that he could get his errands done before 7:30 in the morning. He would sit in the cockpit all day long, first with his breakfast, then with his computer, watching the birds and enjoying the sun.

At some point midsummer, when we’d finally finished an eight-month and far more expensive than anticipated mast renovation, we decided to sail up the Chesapeake Bay for a few weeks and work from the boat on-anchor.

Three months in, we hadn’t come up with any reason to return home to Virginia other than to sell our cars and keep going. When we had left the dock, we said goodbye to cars, reliable showers, laundry, AC power, and an endless supply of water. Our liveaboard boat life at the dock had been rather posh when you look at it that way. On anchor, our systems were tested. Our solar panels could barely keep up with our power usage, so we installed new lithium batteries and a wind generator. Our septic tank filled up in a week, so we installed a composting head. We showered in the cockpit with a pressurized bucket—in swimsuits if it was daytime, and when fall crept in, we boiled the water on the stove. We had to launch the dinghy to get to shore, and if it was rough out, everything would get wet. We were self-sufficient, off the grid, and it was liberating.

The decision came over us slowly, both of us, to never go back to the old way of life. It was like truth had been knocking at our door and we were about to close the door and say, “No, no, we’re looking for truth.” This wasn’t the dream we had planned—to quit our jobs and sail to the Caribbean. This was the dream that was being handed to us if we could keep ourselves from standing in the way.

“So, are we making the decision to keep going?” Josh asked.

It was the first day cool enough to feel like fall, and he had taken off the collared shirt he’d put on over his shorts for his performance review in the cockpit. His boss had just given him the green light—no need to return to the office when this was all over. My work, more or less, had told me the same. It wasn’t without constraints. We couldn’t leave the country with our computers, and I had to be able to travel from wherever we were, once travel picked back up again.

“Yes,” I said, “Let’s keep going.”

By March, we had reached the southernmost point of our journey—a tiny turquoise refuge in the otherwise exposed Florida Keys, where the wind always blows, the sun always shines, and the mangroves are always sending shoots to create new life. It was the end of our journey, but only geographically speaking, like climbing to the top of a mountain and then climbing back down again.

Sailing, as we’d learned by now, wasn’t all wine and cheese. We had encountered such large and sporadic waves off the North Carolina capes that they had sheared several eight-inch bolts straight out of the deck and tossed our home all across the floor. We had learned to pick our weather windows more carefully. We had gotten into a routine; latch the fridge, stow the wine glasses; she moves. Our weekends were 48-hour offshore sails along the coast to make progress, switching night shifts and sleeping when we could. I hadn’t quite grasped the vastness of the Eastern Seaboard until we decided to sail from the Florida Keys to Maine all in one year, while working full-time, only sailing on weekends and traveling at an average speed of five knots.

We learned, slowly, that the realization of dreams happens in moments, when it suddenly dawns on you that you are here, sailing in clear teal water and rolling waves. You are tired and something on the boat is inevitably broken, but this is what you wanted all along, even if not precisely how you planned it.

Today’s moment is in St. Augustine, in the brown, muddy water where my grandfather first launched his boat. I step outside after work to see the sun and remember what city we’re in. The boat has swung around on the anchor, and it takes a second to orient myself to reference points on land. West of us is the fort. South, the drawbridge. North, our route for the day.

We’re going inland after work up the Intracoastal Waterway to Jacksonville, to chop a few hours off our next offshore passage. The ICW consists of canals and rivers that’ll take you all the way from Florida to Boston without ever having to touch the ocean. But for most of it, our keel is too deep, our mast too high, and our work schedules too regimented for drawbridge openings, so we take it in small doses.

We turn into the Tolomato River, and the air starts to change. There is a smell I can’t quite put my finger on, but I know it. There are palm trees and deciduous trees and Spanish moss on the muddy shorelines, and boathouses and beach houses and jet skis and water skiers. People wave from restaurants, watching as we motor past, then easing back into their conversations. Ling Ling looks so big in a narrow river.

Out on the deck, I breathe in deeply and I can’t quite get enough of it. What is it, that smell?

“It smells like home!” I shout to Josh at the helm. Is it the trees? The mud? The river? It smells like another time, a time before when I was small and I swung off a rope swing into the water in my grandma’s back yard.

I look up to watch our 61-foot mast go under a series of 65-foot bridges. Plenty of room, but it’ll take your breath away every time. We drop the anchor just north of the third bridge and watch the currents for a while to see where she settles. The currents are rushing, and the anchorage is narrow. Too much chain and we could hit the bank or sit in the channel; too little chain and we could drag. This is why we prefer the ocean.

As I’m tidying up down below, I notice my mother’s photo album on the wall—the scrapbook of my grandfather’s sailboat, and it seems only fitting to bring it out now, here in Jacksonville, where it all took place. Page after page, in small sepia photos, the boat comes together, all three hulls, giant next to the men who stand beside her, pulling, pushing, painting, hammering, varnishing.

Next to the photos, my mother had left these little cursive gems—“She floats!” and “Ready to go” and “Jane relaxing while the men worked.” There was my grandma even then in her big blue chair by the window next to a lamp in the shape of a pineapple. To see my grandpa in a place I knew so well gave me this odd sense of familiarity—like I could reach out and touch him where the edge of the universe circles back onto itself and there is nothing on the other side but our shared dream.

There he was, sitting at my grandma’s kitchen table, poring over boat plans, in that same place where I had sat too. The wallpaper was light blue, Grandma would read the obituaries while we picked out the Lucky Charms, and if you ever stood up, she would ask you to get something—milk or orange juice, or could you put a pillow under her leg?

There he was in the garage that we would sneak into, climbing in through the back window to sit on the antique riding lawn mower with its deep leather seats. Eventually, the boat got too big for the garage and according to my mother’s notes, they had to dig a trench to get it out.

And finally, “The Launching,” when they somehow pushed all three hulls across the grass and into the channel, where we used to jump from a rope swing in the summers and where once an alligator came onshore to die. The men stand beside the boat in waist-deep water, and I know how the mud felt between their toes.

I know how the story ends, but it still takes my breath away even now when I turn the page. First, it is the finished boat—photo after photo of varnished teak, the galley, the cabinets, the walls, the shelves, even the head. It is, as my mother writes, “Ready to go.” But, as I was told growing up, my Grandpa Jack had a stroke shortly after these photos were taken. He lost his balance and could no longer sail. Ten years later, he died. He never sailed his boat past the mouth of the St. John’s River.

This alone is very sad—a dream never achieved. “He wanted to build the boat,” my mom would say to console me. “He built the boat.” Then she would pause. “And he never knew what came of it.”

When I turn the page, I can hear the breath leave my mouth. There are six pictures of what entropy will do to an unloved boat. It is a pile of plywood strewn about the grass—materials he had meticulously measured and cut and glued and hammered, varnished and polished and launched—in a heap among the trees. One entire hull leans over on its side, the rest is debris. Eventually, my dad had to cut it up and haul it out. But I had never imagined what that looked like. The galley was still intact, like a shipwreck with the bed still made underwater.

“The End of the Dream, 1987,” my mother wrote. A dream without a captain is just a pile of plywood. I study the debris in the square, glued pictures, and I cry. At his dream, at mine, at the frailty of life, at the number of sunsets we have left.

The golden light of today is already hitting the chart table, and Josh calls me out to watch it. “You’re going to miss it,” he says.

I never used to watch the sunsets before. We stand on the deck like it’s our front porch, as the birds fish across the channel, and I lean my whole body against him. Men wave from lawn chairs on the fly bridge of a massive tugboat returning home at the end of the day. It is the kind of wave that means something, that says, “We appreciate this moment, too.” The captain sees us waving and honks his massive horn in response. It is so loud in the quiet river that we can’t help but smile.

Permission required for reprinting, reproducing, or other uses.

Jessica Wilde is a writer and filmmaker who creates content for NASA and other government clients.


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