A Mother-and-Son Sailing Adventure

The truth is, at first, she didn’t really consider bringing the boy.

In fact, a powerful part of her wasn’t sure she wanted to.

It was the same part that had pushed her multiple times through the WaterTribe Everglades Challenge—300 unsupported nautical miles in a kayak through Florida’s labyrinthine, mangroved wilderness. That had jumped aboard a 6,000-plus-mile, two-month-long yacht race from Auckland, New Zealand, to Fukuoka, Japan, after spotting an ad for an all-women’s entry that needed one more crew. That had convinced the leader of an expedition up Mont Blanc—at 16,000 feet the highest peak in Europe—that she was perfectly capable of making this her first real high-altitude alpine climb.

There is an element of Kristen Greenaway’s character that thrives on pitching herself against the odds and that craves the deeply personal challenge of solo endeavor. And even though her role now as president and CEO of the Chesapeake Bay Maritime Museum—a job demanding the unrelieved navigation of political and social intercourse—seems to proscribe solitude’s pure self-containment, there’s one place she knows she still can find it: sailing Magdalena, her 1986 Cape Dory 32.

And so, when the museum’s board granted her a two-month “sea-battical” in the summer of 2022—eight years after she’d started running the museum, two years after guiding it through the shutdowns and economic hardships of the Covid-19 pandemic, six months after the museum launched the new Maryland Dove, its five-million-dollar, first-ever build of a ship from the keel up—she was bloody ready to go sailing alone for a good long while. Two months from the Chesapeake up the East Coast to Maine and back. Bliss.

So, at first, no, she didn’t consider bringing the boy. And anyway, he’d probably be happier pursuing his true passion of playing golf, staying umbilicaled to the internet, hanging with friends.

Also, there was Lori, the boy’s other mother and Kristen’s wife, who wasn’t entirely sold on extended sailing without a shower, truth be told. The thought of their only son on that ocean—nothing between him and a thousand feet of water but a sliver of fiberglass—wasn’t comforting.

But then one day they were all at Fawcett Boat Supplies in Annapolis where Kristen was gathering gear for the trip, when the boy stepped out from behind a clothes rack fully kitted in a brand new set of black Gill foulies, gloves, and seaboots.

At 6 feet, 3 inches tall, their boy, Andrew, suddenly didn’t look like a 15-year-old American teenager who trashed his room, listened to unfathomable music, and couldn’t seem to quite fit into his own arms and legs and body. He looked like a goddamn Viking.

“Well,” Lori said, breathless at the sight of him, “I guess he’s got to go with you.”

And seeing him there, feeling time rocket past her while she stood still, Kristen thought that while it might be true that part of her didn’t want to bring the boy, a part of her surely needed to.

Day 1, 6.3NM: Cast off 1800hrs, eating pizza from tinfoil cooked at home. 13k southerly so good headsail sail to Tilghman Creek. Anchored, stripped off and with mask and snorkel scraped off barnacles on the prop. Boat feels very heavily loaded—boot stripe lowest I’ve seen it!

How many years had restlessness defined her? Her mom and dad—a teacher and a furniture maker, respectively—had bundled her and her little sister aboard a 32-foot wooden sailboat her father built, spending formative wonder years exploring New Zealand’s Bay of Islands. They returned home with a baby brother.

“We lived on the smell of an oily rag for many, many years. All the money went into the boat,” she says. Every summer school holidays, for years after returning to land, the family would take off and head for the Great Mercury Islands for six weeks, a small archipelago off New Zealand’s North Island, where Kristen and her siblings later would spread their parents’ ashes.

“You’d come back to school, and everyone would say, ‘What did you do over the holidays?’ And we were the only ones who had gone away and had a great adventure.”

Probably no surprise, then, when she started gathering her own boats—first jamming a sail into the family’s dinghy, then sailing a Laser while at university, a windsurfer, then a William Garden-designed 18-footer she found on the hard and worked on during weekends. After the first launch, she says, “My brother and I slept on it for four days and nights, bailing. So, I had some adventures on that.” She followed on with a 27-foot New Zealand-designed Raven.

Eventually, she discovered other ways to feed that restless soul—mountaineering, big-boat ocean racing, expedition paddling. But as anyone who’s ever grown up barefoot in sailboats knows, it never leaves you—that freedom of movement under sail, the anticipation of the next landfall or anchorage, that sense of wonder and possibility imbued in even the humblest of boats.

When she came to run the museum on the Miles River in St. Michaels, Maryland, in 2014, the boy was just 7 years old. Two years later, she found Magdalena, which had come to the museum’s charity boat donation program after sitting unused for five years on a mooring. She thought she’d be sailing every weekend, “like when I was a kid.” But life, and pouring herself into the new job, intervened. Still, just knowing the boat was there, a few steps from her office window—that was enough. Mostly.

She usually sailed solo, weekends or the occasional four- or five-day trip. Sometimes the boy joined her, mostly enjoying the days motoring on an even keel. During the pandemic, while the family was in close quarters for more than a year and she worked from home for nearly two years, she went out almost every weekend—even in the depths of winter with no onboard heating. She and Lori joked that it probably saved their marriage.

“I always thought of sailing as a true adventure, and the closest you can be to raw nature, with a hint of danger and having to be entirely reliant on yourself—especially when solo,” she says. “I really wanted Andrew to be able to experience that and develop a sense of courage. Since he didn’t grow up with it as a baby, as I did, that’s not inherent with him. You have to learn that courage, and trust in your vessel. And your captain.”

Day 2, 31.2NM: Awake at 0330 and up at 0530. Put the kettle on and raised anchor while Andrew still asleep. Truly off at 0610!

The first thing you don’t want to do as a sailor—or as a mother—is to screw up and scare your people. And yet, it’s inevitable since we’re human, and in both roles, opportunities are rife. And they frequently occur just when you are feeling like you might actually have your shit together, until karma serves up a little reminder that you are, after all, utterly fallible.

How many miles had she sailed Magdalena solo in the Chesapeake Bay without incident? How many channels and anchorages successfully navigated?

Until daybreak the third morning into their trip, when she motored Magdalena out of the anchorage behind Reedy Island, just south of the Chesapeake & Delaware Canal where it meets the Delaware Bay. Timing is key for getting down the Delaware—an adverse current can slow you to a miserable crawl—and so of course she’d done her homework, which dictated leaving by 0500, and then they slammed abruptly and shockingly into a unmarked portion of a dike that’s invisible in the muddy high-tide water (fellow-sufferers would commiserate on her Facebook page that this notorious spot had sunk more than a couple of unsuspecting vessels).

They were making 5 knots. She crashed into the wheel; the boy slammed hard into the cockpit bulkhead. She immediately cut the engine, and after a second smack onto the dike, the boat swirled 180 degrees and bounced off.

She rushed below and started yanking up floorboards, looking for the telltale ingress of water. Nothing amiss, she told Andrew, forcing the calm confidence into her voice, we’re all good.

But the entire day traveling down the Delaware she’d check and check again, heart in her throat each time. And the next day, in the clear, chilly Atlantic, she dove on the hull to have a look. Thanking her stars for choosing the Cape Dory with its full keel and bulletproof build, she found several ugly divots chewed out of the front of the lead keel but no further damage. The boy, though a bit bruised, seemed reassured.

A week later in Connecticut, she had the boat hauled and the damage repaired while she and the boy took a couple of lay days staying with friends on land and visiting the local attractions.

“The third morning!” she says, still appalled by the accident months later. Adventure can be a freighted word.

Day 5: Cape May, woke up 0540—up and engine on. Raised anchor while Andrew asleep and left with the tide. 1130 turned off engine. Wind 8.3k SE, sailing 4+k. Feel so very happy!

Day 7: Barnegat Inlet to Sandy Hook. Rain started—fairly smooth going out the entrance—couple of medium rollers. We both put on full wet weather gear. Andrew didn’t last long and spent most of the day below. Had the genoa up for a while, then down—motor on the entire time. Andrew not happy to raise even a reefed main and the lean still bothering him.

There is a reason teenagers tend to segregate themselves safely from their parents up in their rooms, and whether we, as parents, like it or not, it’s generally better for everyone. But on a 32-foot Cape Dory, the only privacy is in the head (rather a snug fit for the young Viking), perhaps up on the bow or whatever end of the boat where the other person isn’t, or somewhere not on the boat at all, such as on a distant beach where no one can hear you scream.

Everything else is an exercise in acute cohabitation.

In all her adventures, whether mountaineering or sailing, Kristen knew the necessity of minimizing gear drift—keeping everything where it should be, so you know where it is as soon as you need it. True, there’s a bit of the control freak built into this ethos, but you don’t want to be rummaging through lockers looking for the manual bilge pump handle, for example, if the primary has quit and there’s water around your ankles. And, the fact is, even 32-foot sailboats are notorious for mysteriously swallowing items without any extra help from a 15-year-old’s generalized detritus burying them.

So, there was that—trying to corral the bits, bobs, T-shirts, and undies that invariably followed in the boy’s wake. And the “music.” Really, how could he stand it?

And then, there was the phone.

If you’re far enough offshore, the phone becomes a moot point, but Kristen had made the decision to make the trip up the coast in a series of day hops rather than ask the boy to undertake an offshore passage at this point in his sailing career (back to that bit about not scaring your people). Which meant that rather than paying attention to what was going on around him—other than helping with his assigned tasks—the boy was nose down in his phone for a distressing amount of time. The wonder, she wanted to yell as they sailed, was out here, not in there!

The inevitable conflagration, which sparked in small spurts at first, finally blew up about two weeks in.

Andrew no interest in decent food so made my own. He has no interest in being of any help—to the point of not doing anything asked to do, and now playing horrible music—just pathetically rude. Not happy how upset I am and how I yelled at him but I’m near to tears with frustration and how he just doesn’t care one iota. Lori turned off his phone but he’s downloaded everything. Went to bed on dusk—he turned his very loud “music” off after a long while. Multiple texts from Lori trying to help and keep me sane. Slept well, ironically.

The next day, she made him tea and pancakes and explained why this trip was so important to her; she’d always wanted to have an adventure on her own boat, and to do this with him. He snarked back at her, “How long did you take to practice that speech?” Then he grudgingly ate his pancakes. But not long after he helped raise the main and anchor, and even sailed the boat for a while. Then he went off to read his school lit homework, The Count of Monte Cristo.

As for the phone, it stayed onboard to be used in a more limited fashion, and in fact came in rather handy now and then, such as when the boy used it to find a last-minute slip when the better part of valor meant abandoning the day’s planned passage due to nasty seas and a disintegrating forecast. Instead, he found them a night at a posh marina—a rare treat. Didn’t even need the dinghy to get off the boat to find a metaphorical distant beach, excellent restaurant, and stretch the legs.

Turns out, defining boundaries and finding forgiveness are as important to a successful adventure as they are to anything else involving mother and son.

Day 18: Left Provincetown at 0500 for Gloucester, 45NM. Main and genoa up but motor on the entire trip. Highlight was seeing two right whales on Stellwagen Bank! Gloucester a terrific port, even in drizzle. Wandered town all late afternoon, the Fisherman’s Memorial top of the list. Terrific chat with Jay at the local maritime museum—we were drawn to his shed as we could smell the linseed oil he was dressing with—he was thrilled we were from CBMM…

Day 19: Left Gloucester 34NM to Kittery/Portsmouth. Two lighthouses passing Cape Anne. Quite a sporty day! Consistent westerlies 20+ knots, topped 28, 40 degrees off the bow. Passed Isle of Shoals. Now on a mooring in Pepperell Cove after trying in vain to find an anchorage in our first port in Maine. Our eighth state. Still blowing a consistent 20+.

Working your way up the East Coast day by day can become a bit of a slog, but by the time Magdalena got to Maine nearly three weeks in, something kind of wonderful was happening.

The shipboard routines were set: On the third night she had let Andrew know that he would be washing the evening’s dishes from here on. And he did faithfully every night, except the once when everything blew up. He was also in charge of raising the anchor (without a windlass—good thing he was a young Viking after all) and cleaning the foredeck and chain. She would set it, with him on the wheel and engine. They used hand signals to communicate, proud of their teamwork. He excelled at picking up mooring balls, and he also raised the main each time. Once, she started raising it while he was still in his bunk and he jumped on deck saying, “That’s my job!”

Another day, beset by heavy fog, they meandered carefully for hours toward Moscungus Bay from Seal Bay on Vinalhaven, and Kristen was grateful for the AIS on Magdalena’s new Icom VHF, “and an excellent first mate who stood watch with me for nine hours.”

Most of the time she sailed the boat solo, and she was happy alone in the cockpit in sun and rain, adjusting sails, making navigational decisions. Ironically, their closest times together were off the boat, adventuring on land—a long walk around Richmond Island north of Saco Bay, wary of the marauding horned rams while eating the last of the season’s red berries; exploring the trails, secret coves, and headlamp-lit bunkers of Jewell Island in Casco Bay; climbing Acadia National Park’s peaks while Magdalena rested at anchor in Somes Sound; even exploring (and spending) at L.L. Bean’s flagship store in Freeport.

They visited Winslow Homer’s studio on Prouts Neck and the home of Admiral Robert Peary on Eagle Island in Casco Bay, and even crewed on the 68-foot 1938 Sparkman & Stephens yawl Black Watch racing in Boothbay Harbor Yacht Club’s Shipyard Cup Classics Challenge (not surprisingly, the skipper put the young Viking to work on a grinder).

They (or at least she) enjoyed days of spanking sailing, dodging storms and sailing through a few, and meeting new friends who, in typical sailor fashion, helped them find necessities like laundry, groceries, and ice cream. He was amazed that every time she met someone new, they’d become best friends. “How do you do that?!” he asked.

They marveled at the sunsets, how the color melted from orange to the deepest blue-black over the pointed firs. They cursed the lobster pots, berated the fog. They searched for mussels and scrambled over granite islets and never stopped being astounded at how the big Maine tides changed the view in each anchorage, every six hours. And in the evening, they played multiple games of Uno.

When the time came to begin the trip home, there was more than once glance cast backward.

Day 58: 54NM today, from Atlantic City NJ to Lewes DE. We left at 0430 and enjoyed a terrific sunrise. Conditions very different from yesterday’s—motored the entire way and pretty much glassy. Why Lewes? I’d lost a day somewhere and was reminded in a phone call last night that the boy needed picking up tomorrow to prep for school start on the 29th. He was dutifully picked up, so I’m now solo for the next week to home. Bit sad, actually. He’s good value.

Later, Lori would tell her that Andrew talked about how proud he was of her and her boathandling skills. Every time they’d come into a tight fuel dock or the occasional crowded marina in a howling wind, he could see the male staff standing on the docks obviously nervous about this white-haired woman on the helm, “and then she’d bring the boat in, miss everyone by planned millimeters, and kiss the dock, every time!”

She was happy to know that he recognized her skill. She was proud of the planning she’d put into this adventure—talking with museum shipwrights and friends who’d already sailed these routes, lugging charts and picking their brains, researching itineraries and ports, even investing in lithium batteries, solar panels, and a composting toilet—all to make Magdalena more self-sufficient.

She knew she’d likely not get time like this with Andrew again—though he said he felt ready for an overnight passage next time. She knew that at 15, he might not recognize the voyage as life-changing or character-building, but she believed that in time, he would look back on his experience with pride and realize that he did achieve something quite different and perhaps even exceptional.

In the end, she found some solitude aboard Magdalena, making her way back up the Delaware, through the C&D, and into the Chesapeake, where she deliberately slowed down, stopping in a few of her favorite haunts. She spent the final night in the creek, just 6 miles from home, where she and the boy had begun two months and 1,582 nautical miles earlier.

Time would rocket past again soon enough, nothing she could do about that. The boy would be gone in the blink of an eye. But for just one summer, she’d managed to slow it down for both of them. On this night at anchor, she washed her own dishes, and savored the bittersweet reality of homecoming. 

By Wendy Mitman Clarke with Kristen Greenaway

May 2023