The sailboat glided through the Tortola harbor, and I was at the helm, weaving around docks, mooring balls and yachts at rest, en route to open water. Dinghies buzzed around me, running errands for the larger vessels. And then it happened. A wheezing cough. A resigned sigh. Silence. The motor ceased to putter.
Typically, when faced with a nautical challenge, I would turn to my father for help. A seasoned sailor, he could resolve any issue at sea. He would try to coach me to safety, though in most cases I would just hand the captain’s hat back to him like an impatient child. But this time was different. My father was at home, in Massachusetts. And even if he were reachable, he could not have assisted. His mind no longer remembers how to operate a boat, and he has lost the ability to shape the ideas and speak the words required to rescue me.
More than three years ago, he was diagnosed with Alzheimer’s, which eventually forced him to stop sailing and sell Kaila, the 40-foot Tartan he and my mother had owned for more than a quarter century. It is also the disease that landed me in the British Virgin Islands, on a vessel with a phlegmatic engine, swirling in a vortex of wind, waves and emotion.
My mother never tires of telling the story of how my father, a product of the Bronx, fell into seafaring. When they were dating, she told him that she would consider him a serious suitor only if he shared her affections for dogs and sailing. Smitten, he started taking lessons on the Charles River in Boston. Over 55 years of marriage, my parents have cared for eight dogs and five sailboats. (Oh yeah, and two daughters.)
My father embraced sailing with a sportsman’s dedication and a devotee’s fervor. He spent summers zipping around Long Island Sound, clocking anywhere from hours to several days on Kaila. During colder months, he and my mother would travel to other climates and hemispheres to get their fix. They chartered boats in New Zealand, Croatia, Greece, Turkey, Sardinia and Tonga. Instead of winter breaks in alpine mountains, we spent the holidays sailing around the Caribbean, surrounded by palm trees strung with Christmas lights. For my father, throwing off the lines did more than free the sailboat from its tethers; it released him, too.
“He never took anything for granted,” my mom recently told me. “He loved to chart the course, trim the sails, and sail as fast and as efficiently as possible.”
Some parents hope their offspring attend their college alma mater or tread in the same professional footsteps; my father just wanted his daughters to master the art of sailing. But I was a typical teenager, caring more about the immediate satisfactions (tanning, napping, listening to my Walkman) than the longer vision.
Still, as a devoted daughter, I have always wanted to make my father proud, and more so now that the cranks and wheels of his mind are winding down. So on a wintry afternoon in Massachusetts, I presented him with a surprise.
“Dad, I am going to earn my captain’s certification in the British Virgin Islands,” I told him.
He looked at me with a bewildered expression. I explained that once I passed the test, I could take him sailing. For the first time in our family’s history, I would be in charge.
He often speaks in fragments separated by long pauses, but when I asked him for advice, he responded in a clear voice.
“Be humble,” he said.
Matt Holt found me lounging at the marina pool — old habits die hard. The manual “Sailing Made Easy” rested on the chaise, cracked open to Chapter One: “The What, the How, and the Where.” I could answer at least one of those questions without stepping on deck. The “where” was the Mariner Inn and Marina on Tortola, the training base for Sunsail.
Matt was the chief instructor at Sunsail and an architect of the company’s sailing school, which he helped establish in 2004. (The company also charters boats.) He was going to cover the Basic Keelboat Sailing course, the first part of the 10-day program and the gateway to more advanced training: Basic Coastal Cruising and Bareboat Chartering. The lessons would consist of on-water drills and written exams. If I passed all three, I would earn an American Sailing Association certification, joining half a million sailors licensed to charter a sailboat at any ASA-affiliated company around the world. Though in my case, my primary goal was to borrow a sailboat for a few hours.
“We will give you enough knowledge to begin your journey,” Matt said. “We are big on situational awareness. Did you bring enough supplies? What do you do in a thunderstorm or if there is a rock in the way?” (Foreshadowing of the dead motor incident, perhaps. After a failed attempt to sail the 26-foot Opal Bella and her stalled motor back to the slip, we had to hail a dinghy to tow us in.)
I followed Matt past tight rows of boats to our temporary digs, a brand-new Jeanneau Sun Odyssey. I leapt over the small gap between the dock and the boat in my flip-flops. I descended the stairs with care, remembering the time my mother slipped on Kaila’s steps and fractured three ribs.
I surveyed the main salon, which seemed at once strange and familiar. There was the navigation desk, with its knobs, switches and lights, and the galley, with its grab-bag-style cooler and propane stove. In my V-berth cabin, I opened the hatch, filling my snug space with the sounds of sailing: halyards tapping against the mast, wheelbarrows rumbling down the wooden docks, beer bottles clinking. I felt a pinch of nostalgia that was part ache, part joy.
Class didn’t start until the next morning, but I dove into the first unofficial lesson: Know your shipmates. Recreational sailing is a team activity, and the stresses of working as a unit in challenging conditions can elicit the best (helpful, courteous) and worst (domineering, abrasive) personality traits. At sea, my father never raised his voice, even when we were headed toward danger. Sam and Linda Ward, who run a fishing tour operation in Arkansas, belonged to the same cult of crewmanship. The couple invited me to dinner at the marina, and over a casual meal of seafood and salad, we explained the forces that led us here.
“I want to become proficient and be able to take care of things if there is a problem,” said Sam, a septuagenarian who wore a lusher version of the Colonel Sanders, complete with winged mustache.
Linda was simply on vacation, a supportive mate with no real interest in sailing beyond her husband’s. She toted paperback mysteries and other novels, not the heavy manuals Sam and I hauled around like prayer books.
For the three-day introductory course, the Wards and I slept and studied on the yacht but never sailed it. Matt held the on-water classes in a Colgate 26, a day sailor with an outboard motor, a tiller and manual winches. He called Opal Bella the “bicycle before the Harley.”
On the first morning, Matt, bouncing with energy and coffee, gathered Sam and me around the galley table. He pulled out a whiteboard and erasable markers. “The whole industry is based on the premise of having fun,” he said before launching into a brief history of sailing, touching on sea monsters and the Earth-is-flat theory.
As Matt discussed the basics of sailing, several fragments from my past snapped into place. I watched these once random bits fuse into the foundation of my knowledge. That groaning noise I always heard under the floorboards of Kaila? Turns out it was the bilge pump vacuuming up excess water. My father’s practice of sailing into the wind to raise or lower the mainsail? He needed the boat to float in the dead zone, to avoid getting tossed around. His use of the nursery rhyme-ish “hard-alee”? He was informing his crew that he was turning the bow into and through the wind. From now on, I would shout “hard-alee” with pomp and conviction.
“In 45 minutes, we just covered 70 percent of the exam,” Matt said.
Before wrapping up the lesson, he placed several pieces of line (don’t call it rope!) on the table. He demonstrated some of the main knots without looking down at his hands. Then it was our turn. Sam knocked off a square knot and a clove hitch. I focused on bringing the bunny around the tree and up the hole. I presented Matt with my creation, unsure of what I had tied.
“That’s awesome!” he exclaimed. “You tied a bowline. That’s one of the hardest knots. I can tell that you have been sailing since you were a child.”
For the remainder of the week, he introduced me as the Student Who Tied a Bowline Without Knowing It.
The Inner Harbour was as contagiously spirited as nearby Road Town, the capital of the British Virgin Islands that Tortola has the honor of hosting. Hotels, shops and warehouses battled for space along the wriggling coastline. Above, peaked-roofed homes cascaded down avocado-green hills. Catamarans and sailboats flowed in and out of the marina. Cruise ships loomed tall and wide, casting a menacing shadow on the aquamarine water.
For our inaugural sail, Sam threaded the boat through the mild chaos while I pointed out oncoming traffic, a don’t-crash course on right of way. Matt directed us to a swath of water facing a crooked smile of islands. We raised the sails in 20-knot wind, and just as we were humming along at a comfortable clip, he told us to tack.
“Ready about?” I asked my crew.
“Ready,” responded Sam.
“Turning and release,” I commanded. The boat turned, and Sam released the sail, just as the captain ordered.
To be sure, we had some sloppy moments. I am amazed that after several battering moves, our sails didn’t tatter like rags. But we were quick to respond and fix our mistakes.
“You both did a really good job,” said Matt, back on shore. “A toast to Bella, which is really a toast to her crew, because she couldn’t go anywhere without you.”
Sam piped in. “The whole thing was wonderful,” he said. “When we were heeling over, after one or two times, I started to relax. I knew that we weren’t going to crash or sink.”
I was too drunk on sea spray and adrenaline to say much. But I knew that today, I had sailed like my father’s daughter.
I was last in Tortola for a family sailing trip, an adventure we would never reprise. During the changeover to a new boat and instructors, I wandered around the marina, remembering. The apparel shop where my brother-in-law bought a bathing suit after the airline lost his luggage. The provisions store where we shopped for supplies that leaned toward salty snacks and a bottle of rum. The bathhouse where we enjoyed the only real shower of the week.
For the second and third courses, we lived on the 50-foot La Bella Vita and sailed from port to port like bona fide cruisers. Mick Fagan, our English captain, piloted us toward Trellis Bay on Beef Island, a bulb-shaped harbor with stands of palm trees, a silky beach and a restaurant and bar called De Loose Mongoose. On the sail over, he wove together lessons with stories of his harrowing transatlantic crossing and full-throated singing of Irish fighting songs.
“The boom is the best windvane,” said Mick. “Check the waves and feel the wind on your cheeks and ears. These are all things old sailors would use, and I consider myself an old sailor.”
We settled in at our mooring under a sky awash in tropical-drink colors. Mick and I motored to shore to reserve a table for dinner. For Super Bowl Sunday, the waterside restaurant had installed a supersized screen on the sand. Locals and sailors gathered at picnic tables covered in buckets of beer and seafood skeletons. I sat beside an Englishwoman pursuing her Royal Yachting Association certification (the Brit version of ASA) with her brother. I tried to explain the rules of American football but never advanced beyond the personal bio of New England Patriots quarterback Tom Brady.
The exercises were growing more complex and difficult: navigation by leg dividers and a parallel ruler; docking in 30 mph wind; sailing around an entire island; trying to rescue Mick’s hat, which blew overboard. Add to the pressure: commandeering a boat as long as a humpback whale and worth about a half-million dollars. But during a jibing drill — directing the stern into and through the wind — I let go of my inhibitions.
“How fast am I going?” I asked Mick, who was cupping a cigarette against the wind.
“8.4 knots,” he replied, peering at the speedometer.
A personal best.
“We’re flying,” shouted Sam, who exceeded 8 knots during his turn at the helm.
The ASA doesn’t require a night sail, but Mick proposed an adventure after dark, leaving Leverick Bay on Virgin Gorda at 4 a.m. We crawled warily out of bed. Mick made sure that we were all tethered to a safety line. The stars shimmered like tiny sequins. Mick pointed out the rare celestial occurrence of the North Star and the Southern Cross inhabiting the same sky. We silently sailed out of the channel, relying on buoy lights to lead us past a reef described on the nautical chart as the “graveyard of many bareboats.”
I was behind the wheel and searching for any smudgy outline of land. I let Mick’s voice, and the glowing ash of his cigarette, guide me. “Go straight till you see the little yellow flash on Mount Point,” he said. “The light is not at the end of the rocks. It’s on the headland.”
The sky started to brighten. I was startled to see how many obstacles — rocks, anchored boats, entire islands — I could have hit. I traded places with Sam and curled up in the cockpit, my eyes heavy from the strain and lack of sleep.
Mick allotted us time for a nap before the exam. Despite my drowsiness, I scored a 94.
“This will make you a useful member of a crew,” he said. “The next one will make you a skipper, and you will be qualified to charter a boat.”
We took the last exam at the Bight on Norman Island, a popular anchorage with a Carib party vibe. I sweated the navigation calculations and froze on one question about how to reduce the heel. Suddenly, I imagined a frequent dialogue between my parents.
Mom: “Barry, the boat is heeling too much.”
Dad: “I’ll ease the main.”
I penciled in the correct answer.
I handed Mick my exam and went below. I couldn’t watch him grade. After a few minutes, he called me up, sat me down and showed me my number: 89.
“You knew what to do, but you didn’t know why you were doing it,” he said. “Now you know the parts of the boat and their functions. I’d feel safe leaving you on the helm. You wouldn’t panic. You’d work it out. My recommendation: Get some experience.”
To celebrate, I jumped into the water, my first swim of the trip — and as a certified captain.
Hours after returning from the islands, I called home. “Mom, put Dad on,” I said.
I heard the familiar shuffle and fumble of the phone. “Hello,” my father said in his faraway voice.
My words tumbled out as I excitedly told him about my achievement. I struggled to decipher his garbled response. I repeated my story, slower and with fewer details. “Dad, I am a captain, just like you,” I told him.
“You now recognize how wonderful it is, the business of sailing,” he said, carefully selecting his words. “I am proud of you.”
Three days later, my mother called to tell me that he was in the hospital with an infection. After his health stabilized, she moved him to a nursing-care facility, unsure of when — or if — he would come home.
With profound sadness, I had to scotch my plan of taking him sailing. But I wasn’t going to abandon my promise to honor my father, the captain. I would find a way. Several months later, I boarded the ferry to Block Island, off the Rhode Island mainland, to sail on waters still graced by his valiant spirit.
The Block Island Club rents sailboats on Great Salt Pond, a body of water steeped in personal memories of my father guiding Kaila to her second home. On a Sunday striped with steel-gray clouds, I signed out a Sunfish and pushed it out to deeper water. A gust of wind elbowed its way in and pushed the boat over. I pulled it up. The wind knocked it down again. A club instructor waded into the shallows to help me right the hull.
I slid gingerly inside the cockpit and steered the boat toward the opposite shore. The sail cupped the wind, and the Sunfish picked up speed. I yanked on the sheet and pressed my feet hard against the bottom.
“I’m doing it, Dad,” I whispered in a mix of awe and reverence.
With a few tacks, I successfully crossed the marine traffic lane. A woman lounging in a sailboat from Annapolis waved, and I returned the greeting between sailors. I cut a wide arc around a stand-up paddleboarder and spooked a bobbing cormorant. I stopped thinking about the diagrams and definitions in my course books and allowed instinct and sensation to take over.
Eventually, I found myself by our old mooring. I positioned the boat so that I could pause and reflect on my father. In that still moment, I vowed to continue sailing for the both of us. Then I maneuvered the boat back into the wind, tugging the sail as close to my heart as possible.
Andrea Sachs is a Washington Post staff writer.
Email us at firstname.lastname@example.org.
For more articles, as well as features such as Date Lab, Gene Weingarten and more, visit The Washington Post Magazine.
Follow the Magazine on Twitter.
Like us on Facebook.
Sunsail (888-350-3568, sunsail.com) teaches all levels of sailing from its flagship base in Tortola, in the British Virgin Islands. The 10-day American Sailing Association certification course (ASA 101/103/104) prepares students for a life at the helm and costs about $2,700 per person double and $3,200 single occupancy.
If you prefer land over sea, stay at the Mariner Inn Hotel (284-494-2333), steps from the marina at Wickhams Cay II and a short walk from the capital, Road Town. Guests can hobnob with sailors at the pool, bar, restaurants and a smattering of shops. Rates from $160 a night.
The Block Island Club (136 Corn Neck Rd., Block Island, R.I., 401-466-5939, blockislandclub.org) offers sailboat rentals, charters and classes. To rent, you must purchase at least a week-long membership from $215, plus rental charges. A charter with a captain costs $80 per hour for members and $150 an hour for non-members.