Little Wing Takes Flight

My university announced via email it was sending everyone home due to the pandemic. As inboxes chimed, everyone streaming out of buildings and onto the quad suddenly stopped walking, eyes locked to their phones as they digested the news. Over the next few days, we packed up our dorm rooms, said goodbye to friends, and headed home – my plans for a semester abroad and a summer boat job scuttled.

Around that time, my family was selling our farm in southern Maryland, and the buyer happened to have an old sailboat in need of a new owner. She hadn’t touched water in decades. My dad and I drove to the boatyard just a few miles down the road and found her coated in pine needles and guano. The owner had lost the key years ago. She was 30 feet, full-keeled, and made of steel; everything that could be overbuilt and welded on was exactly that. So we incorporated the boat into the farm sale as a trade for our old tractor, and I became a 20-year-old boat owner.

Becoming Seaworthy

Thoughts and plans buzzed through my mind like mosquitoes. I cut the lock off the cabin, powerwashed, shop-vacuumed, de-wasped, and filled garbage bags with moldy, decaying gear. The systems were toast, so I ripped them all out. Within a month I had an empty hull after my dad and I removed the original rusty engine via an improvised crane system that included the boom, a rented chainfall, and a whole lot of sailors’ vocabulary.

The goal was to get her floating and self-propelled, and move her to Annapolis where I could finish the refit in the water. I sanded and painted, and when my dad was available, we wedged ourselves into the oven-hot engine compartment, snapping drill bits and sliding around in our own sweat as we attempted to align the new Volvo 30-horse engine. There were many setbacks, including the new transmission that fell off the delivery truck and then was replaced with the wrong model. We had a custom fuel tank fabricated, wired the engine to a single starting battery precariously balanced next to it, hired a welder to add and replace some thru-hulls, and installed new seacocks.

The night before splashdown, she hung in the straps while I put the final touches of bottom paint on the underside of the keel and stuck her name on: Little Wing. The next morning, she rolled through the gravel yard, squared up over the well, and descended into the murky Chesapeake for the first time in 20 years. Stepping aboard I found a firehose gushing from somewhere in the V-berth. Wading forward, fighting back tears, I found one of the ostensibly closed seacocks spewing seawater at an extraordinary rate. She was lifted back up, and I poked a flashlight into the unplumbed seacock. It was wide open! I’d installed the handle 90-degrees off. After pumping out all the water, we lowered her back into the drink. This time, no leaks.

On a hazy gray morning in early January, I popped champagne across the bow with my parents, siblings, and Sage, a friend I’d met aboard the Woodwinds who’d agreed to join me. Sage and I slipped the lines and motored out of Back Creek while my family rushed over to their boat on the adjacent dock and followed us out of Annapolis Harbor.

When we reached Tolly Point at the edge of the harbor, my family turned around, and Sage, Little Wing, and I were officially alone on the Chesapeake. It was flat and windless, so we motored the three-hour trip to Tilghman Island, our first stop, anchoring behind the island and settling in for a chilly night on the hook, made only slightly warmer by the alcohol-burning heater. I barely slept, anxiously awakening every few hours to scan the shoreline and quadruple-check that we weren’t dragging. At 2 a.m. it finally hit me: We’d really left!

Casting Off At

daybreak, white caps frothed all around, and wind howled through the rigging. We hadn’t dragged, but the house batteries were dead. I subdued my panic. Luckily, we’d isolated the starting battery, so we got the engine going, motored to the marina on Tilghman Island, plugged in, and figured it out.

Every day was a new trial by fire. While surfing to Deltaville, Virginia, Sage at the helm, I stepped below to make a sandwich, only to watch a dribble of water peek out from between two boards, roll across the floor, and disappear on the other side. The bilges were full. Cabinets flew open as I laid hands on every thru-hull I could think of. They were all bone dry.

The sun was dangerously close to the horizon and we were making bad time, when I suddenly remembered another thru-hull. Near the transom, 3 feet above the waterline, was the output for an old manual bilge pump we’d removed but not replaced. Rolling through the following seas, we were dunking it underwater every few waves, letting in several gallons each time. I grabbed a plug and shoved it in the hole, Sage and I took turns pumping down the water until the bilge pump finished the rest, and we limped into Deltaville in the dark. To add insult to injury, the saloon table uprooted itself and took a field trip to the quarterberth.

“I guess Poseidon doesn’t like eggs,” Sage commented. There was limited room in the electric cooler, so we’d kept the eggs in the cockpit, figuring it was as cold as a refrigerator that time of year. Inevitably, we stepped on them and had been throwing the crushed eggs overboard along the way.

About a week in, we made it to Norfolk, Virginia, and Sage drove a rental car back to Annapolis to square away some bills, pack more clothes, and pick up her dog, Stella, our new third crew member. While exploring downtown Norfolk awaiting Sage’s return, I met Nic, a nuclear and electrical engineer in the Navy who was fascinated by this expedition of mine. We exchanged numbers, but I didn’t expect to hear from him. Sage returned, and we set off for the Dismal Swamp.

That evening, moored to a free dock in the swamp and attempting to warm up by the combined output of the alcohol-burning heater and paraffin lamp, I got a message from Nic: “Did you make it to the swamp? I could come pick you up and we could get dinner. The swamp is only 30 minutes away.” How frustrating that a five-hour trip by boat was only 30 minutes by car.

“We’re in the middle of nowhere,” I responded. “There isn’t even a road.”

“Where will you be tomorrow? Will it have a road?”

“We’re aiming for Elizabeth City.”

“Well, I could pick you up tomorrow in Elizabeth City and we could get dinner?”

The next evening, moored to another free dock in Elizabeth City, I left Little Wing under Sage and Stella’s guard and joined Nic for dinner.

Southern Landfalls And A Boy Named Nic

Sage, Stella, and I continued meandering south with an undetermined end goal. The day before we were set to cross the infamous Albemarle Sound, I checked the weather: a consistent 15 knots from the south. My library of guidebooks advised that, due to the sound’s shallow depth and long fetch, 15 knots was the maximum wind in which a small vessel should attempt to cross. Perfect! We slammed into the oncoming seas for several hours, drenched to our base layers by the time we pulled into the combination truck stop/marina in Alligator River. I ordered what were allegedly fried alligator bites from the truck stop, and Nic and I made plans to meet up again the next day. I needed an oil filter, and he had a car, so our date included driving around various marine and auto parts stores until we found the right one.

We pushed on through Belhaven, Oriental, and Morehead City, North Carolina. Dolphins made appearances as we inched into warmer waters, and one by one we shed our layers and settled into some semblance of a routine. Alarms blared at 4 or 5 in the morning, well before first light. Shivering and grumbling, we cast off and pointed south, then got the coffee going. We took two-hour watches at the helm, arriving at our destination hopefully with enough daylight to explore whatever new town we’d landed in. Life was beating to a new drum.

Before long, I was comfortable chatting with drawbridge operators and other vessels over VHF, and “Bridge XYZ, Bridge XYZ, this is southbound sailing vessel Little Wing just off day marker number whatever, requesting an opening,” rolled naturally off the tongue. I thought I was getting more confident as a driver and docker, too, until, “What do you think that grinding noise was?” I asked Sage after we swung onto an alongside pier.

“You’re throwing it too quickly between forward and reverse,” she said. “The transmission can’t keep up with you whipping this 5-ton boat around like a skiff!”

When we pulled into the marina at Carolina Beach State Park, we settled in for the weekend. Nic was driving down to visit, but before we could go explore nearby Wilmington, we needed to fix the freshwater pump, which had petered out somewhere between the Dismal Swamp and Belhaven. Before Nic drove down, I asked, “Hey, you’re an electrician, right?”

“Yeah,” Nic said warily. “Why?”

“Well, my water pump’s broken. I was hoping you could troubleshoot it when you get here?”

Nic showed up with a bag of electrical equipment and spent an hour crouched over the pump with a headlamp while I asked questions about electrical troubleshooting and he denounced our choice of pump location.

“You know this is the weirdest date ever, right?” he said.

We carried on down the Cape Fear, then into the winding waters and swinging tides of South Carolina. I felt very small when we showed up to our slip at the end of Charleston’s half-mile-long megadock. When we arrived, the tidal current was at full velocity astern, and I could tell we were going to hit that dock. The dockhand was panicking, accustomed to yacht owners who didn’t tolerate even a single scratch to the gelcoat, until I shouted “It’s OK! She’s steel! Don’t hurt yourself!” The dockhand backed away as we slammed into the dock, everyone’s fingers intact.

Onward, through Beaufort, Hilton Head, and Savannah. Anchored on the inside of Sapelo Island, Georgia, Sage convinced me to make the next leg bluewater. The idea of an offshore hop still got my heart rate up, but I accepted the challenge.

A First Jump Offshore

The day we went offshore boasted a perfect 10- to 15-knot breeze, but it had been blowing 25 for the previous several days, and the swell hadn’t calmed down. We dunked one rail then the other in the towering following seas, which Sage estimated to be 10- to 12-footers at their peak. I stood with the tiller clenched between my legs, the only way to prevent it from being ripped from my grip when the next swell caught the rudder. We broke a speed record that day – an unfathomable 13 knots, nearly double the theoretical hull speed. Exhausted, we opted to bail out in Brunswick, Georgia.

To get into Brunswick, we had to turn due west into a 10-mile channel, taking waves directly on the beam. Massive cargo ships departing Brunswick were constantly emerging from the mist ahead, and Sage worked the radio to coordinate passing while I kept an even tighter grip on the tiller.

There was no greater relief than stepping onto the dock at the end of that day, and no greater meal than the pizza served by the first restaurant we stumbled into. That evening, I texted with my dad from the marina’s lounge.

“You ought to sit back and think about what you’ve just accomplished,” he said. “At 20 you just captained a boat that you restored from the brink of death, offshore, in conditions that would have humbled most sailors.”

Staring at the linoleum floor, still damp and looking like I’d just crawled out of the woods, I reread that text over and over through blurred vision.

When we arrived in Fernandina Beach, Florida, Sage had to go home. With my 21st birthday coming up, Nic convinced me that I ought to spend it with at least one other person, as opposed to alone in an unfamiliar port. So Sage, Stella, and I rented a car together, I put Little Wing to bed for a few weeks, and we drove north.

When I returned to Little Wing after my hiatus, I was now truly alone. Any confidence I’d gained during my time with Sage abruptly vanished, and I waited until the waters were glass before casting off singlehanded to Jacksonville.

Meandering deeper into Florida, I slowed down a bit. I stopped in Marineland, walked across highway A1A to a wide open, empty beach and, for the first time on my voyage, I laid in the sand, having finally shed the rest of my winter layers. Staring at the sky, I relaxed. Then my phone rang; it was Nic.

“Here’s a crazy idea,” he said. “I have a week off from work. What if I drove down to Florida tomorrow and we sailed together for the next week? You can teach me.”

He was there the next day. I spent that afternoon acquainting him with the lines, and the following morning we set off for Daytona. We sailed, discovered hole-in-the-wall Old Florida seafood restaurants and tourist junkets, and explored more empty beaches. By the end of the week, we’d made it to New Smyrna Beach, and I trusted him enough to man the helm.

Reaching The Fork In The Road

When Nic left at New Smyrna, it was time to consider my options. I was now more than 1,000 miles from home and needed to get back to school. This was the right place to turn around.

“This is sou-, uh, northbound sailing vessel Little Wing, requesting a bridge opening,” was how it went my whole first day headed the opposite direction. I cleared New Smyrna all the way back to Marineland in one long day. Feeling good about my decision, I stepped into the cabin to start work on dinner and heard a squish beneath my feet. Water spurted up between the floorboards. Ugh, not again.

The bilges were full. There was water in the engine compartment. Was it my dripless shaft seal? I got to work helping out the bilge pump. But water was still coming in, and from somewhere that wasn’t the shaft seal. I poked around with a phone and a flashlight and, employing creative use of boat yoga, caught a video of water streaming in from the side of the metal stern tube that runs inside the boat, between the shaft bearing and the shaft seal. It’s meant to be full of water, but not meant to expel that water out the side. I dug through my emergency leak bag, which contained a wide array of plugs, patches, and fast-curing underwater epoxies. None fit the bill for this particular problem. I stayed up most of the night, timing the automatic bilge pump. Three minutes since it last kicked on. Two minutes and 56 seconds. Two minutes and 52 seconds.

The next morning, I called a service yard in St. Augustine, 30 miles north but the closest location with a suitable lift. The repair took about a month, which I opted to spend in Norfolk. The yard pulled the prop shaft and removed the stern tube. They texted me a picture: It was Swiss cheese, full of holes corroded straight through. I can’t believe I didn’t catch it during the refit. The yard fabricated a new piece, this time made of 316-grade stainless, and reinstalled it.

During my month in Norfolk, I’d applied for and been offered a job aboard schooner Virginia for the summer – great news considering my lack of funds. The hitch? I had to get Little Wing back in time for the start date. A friend offered to join me.

Henry’s primary job was to check the new stern tube every 30 minutes to ensure it wasn’t leaking. It took at least a week underway before I truly relieved him of this duty. We cast off well before first light each morning and often arrived in port after dark to maximize our daily mileage. Winding north back through Georgia, thunderstorms were forecast one afternoon, but based on the radar and our math we thought we’d pull into Jekyll Island just in the nick of time. Instead, the sky opened while we were still a few miles out. It was lucky that we were headed to an alongside pier because, between the near-zero visibility and wind ripping across the beam, our sideways docking maneuver resembled a scene from “Tokyo Drift.”

On and on, retracing my path in the opposite direction, Henry and I landed at the Dismal Swamp Welcome Center’s dock in a miraculous two weeks’ time. This time, I’d chosen a swamp dock that included road access so Nic could meet us and join me on the last day of the trip.

The last day of Little Wing’s Intracoastal voyage was an easy 12 nautical miles. Relative to the 50-, 60-, even 80-mile days that Henry and I had been pulling for the previous two weeks, 12 miles felt like nothing. Nic and I were listening to music when we suddenly turned a corner, and the marina came into view. I fell silent. Nic changed the music so that “Little Wing” by Jimi Hendrix, the boat’s namesake, was playing, and I felt a tear roll down my cheek as we glided into the very same slip I’d stayed in months prior. Nic stepped onto the dock and held out a hand, and after a moment’s hesitation, I took it and stepped off behind him.

Back To The Real World

Over that summer, I worked aboard schooner Virginia and taught youth sailing on weekdays, then continued teaching Nic aboard Little Wing on the weekends. He’s a natural trimmer, navigator, and all-around fixer. Although I never did give him the opportunity to try docking, so there is possibly even more untapped potential there.

Come fall, I returned to college, kept my head down, and found myself on long walks through the upstate New York woods. Nic and I visited each other regularly, and over my winter break, we took a weeklong sailing trip aboard Little Wing. We got snowed in aboard, in a tiny town on Virginia’s western shore, and for a few days the humor of cracking ice off the lines and building snowmen on deck distracted me from the dread I felt about returning to school and looking for a post-grad job.

After graduation, I moved to Norfolk with Nic, and we continued to sail Little Wing up and down the Chesapeake in our free time. I wrote part-time for a local sailing magazine and picked up other oddball jobs to fill the gaps. Nic picked up freelance rigging, mechanical and electrical work, and started photographing local regattas. He’d been bitten hard by the sailing bug.

Eventually, I stopped looking for jobs in my academic field and turned toward the marine industry. Growing up, boats were a great hobby and occasionally a great part-time job, but I’d never considered making a career out of it, until I saw a listing for an opening at BoatU.S. Magazine and applied. They hired me!

In the fall of 2023, Nic proposed at the same marina where we met three years prior, overlooking the Elizabeth River. Considering that we have, quite literally, been in a sinking boat together and not killed each other, I trust we’ll make for pretty good lifelong sailing partners. I even acquiesced to calling Little Wing “our” boat, although Nic had to put in his time sanding the bottom first.

Saving a yard queen was the best worst idea I ever had. I chose the neediest, most financially irresponsible boat in a 100-mile radius and sailed her farther than she ever should have reasonably gone. But Little Wing gave far more than she ever took. Twenty-year-old me, staring up at a moss-covered, decrepit steel hull, had no idea where this old boat would lead her.