19. Sailing While Black: Teddy Seymour Plays His Love Song

Teddy Seymour was born in 1941 and grew up in Yonkers, New York City, across from the freight yard beside the Hudson River. His father worked at an elevator foundry across the street. Teddy grew up outdoors, moving around the city. He had a paper route, fished on the pier, delivered fish and crabs to houses, and picked up any work he could, playing hooky from school if he needed to. His grandfather, who lived near them in Yonkers, had been a fisherman in Trinidad, and he filled young Teddy’s mind with watery adventures. “I never turned down a dare,” Seymour wrote when looking back on his childhood. At age thirteen, as the story goes, he and some friends built a raft from scrap wood, in which Teddy floated down the Hudson River and needed to be rescued by the Coast Guard. In 1956, when Seymour was in high school, the same year Davison published My Ship Is So Small, a global economic revolution was beginning downriver: the first ship to carry containers departed from the port of Newark, New Jersey. The containers were long steel boxes filled with cargo that could be lifted or driven on and off a ship and right onto a railroad car or a truck. Containerization would enable consumer and economic growth unlike anything our world had ever seen, to the point that today, besides bulk goods like oil and grain, nearly all products travel internationally inside one of these forty-foot boxes before being hoisted onto a truck or a train. Few people at the time saw the significance of this invention, the paradigm-shifting impact of “intermodal shipping” that would grease the skids of globalization.

Seymour likely took no notice of the dawn of containerization. He had no plans to enter the merchant marine, and at that point he had not spent any significant days in boats, under sail or power. He was, however, a skilled and hard-working runner, which earned him a track scholarship to Central State University in Ohio, where he earned All-America honors. During college he got a taste of sailing with two of his older cousins who owned their own boats. After graduating, Seymour joined the US Marines. He served in Vietnam, attaining the rank of captain as he excelled in an amphibious landing force, his unit delivered by Navy ships to clear out a beach. “I loved it,” he wrote later. For his tour he was nominated for the Navy Cross for bravery. Later, until 1972, Seymour was stationed as an artillery officer at Camp Pendleton, south of Los Angeles. He served there during the Santa Barbara oil spill, when Sharon Sites Adams returned from her trans-Pacific crossing, and when teenager Robin Lee Graham returned to Los Angeles from his circumnavigation. During his free time, when not running, Seymour learned to sail dinghies while he earned a master’s degree in recreation administration. He bought a day-sailer, then a small pocket cruising boat, and then took out a loan for a larger ocean-going boat named Love Song, aboard which he lived during graduate school and when he worked a job as a production manager at the American Can Company, in the Dixie Cup division. With larger voyages already on his mind, Seymour did his first solo trip out to Catalina Island, about twenty-five miles away. He never forgot sailing alongside basking sharks, “my friends,” with which he sailed in company both there and back.

In 1979, Seymour set out from Los Angeles. He sailed alone down to the Panama Canal and then alone across the Caribbean Sea, a tremendous single-handed passage in itself, finishing in St Croix in the Virgin Islands, where he had previously made friends and secured a job as a primary-school teacher. To fit out Love Song for a world voyage, he did additional odd jobs around the island, including working as a night watchman and as a waiter, keeping the goal of a circumnavigation in his sights. All this time, he still kept up with his long-distance running. With a friend from St Croix he hopped on a plane one year and completed the Boston Marathon.

Seymour’s why-go was not initially to sail around the world by himself. “Originally, I planned the trip with three women, on a different occasion,” he said in one interview in St Croix years later. “They [each] backed out. All along, I was getting ready.”


By the late 1980s, several hundred, perhaps even over a thousand people, had now sailed alone in their own small boats across one of Earth’s oceans. More than people had completed solo circumnavigations, and of that number, at least eighteen, including Robin Knox-Johnston, Bernard Moitessier, Kay Cottee, and Kenichi Horie, had circled the globe without pausing at a single port stop.

Single-handed ocean-crossings had by the 1980s been increasingly bifurcating between the solo “cruisers,” sailors like Teddy Seymour who in the wake of Harry Pidgeon mostly wanted to sail on their own schedules in fair winds and visit distant ports as tourists, and the solo “racers,” sailors who in the wake of Francis Chichester mostly wanted to compete and challenge themselves on a public stage to set a record or sail with, as put by circumnavigator Naomi James in 1979, a competitive “survival element.” Although the cruisers and the racers continued to move philosophically and physically farther apart at marinas and anchorages, the two groups still inspired and informed each other despite their different means and ends. And both solo cruisers and racers kept pushing new boundaries of geography, artistic expression, and the types of people casting off the dock. After his research into traditional navigation in the South Pacific, Dr. Lewis sailed by himself to the Antarctic Peninsula, from which he wrote a bestseller titled Ice Bird (1975). In 1987, young Tania Aebi and her cat Tarzoon completed a world voyage, after which she wrote Maiden Voyage (1989) from her regular dispatches to Cruising World magazine.

The further historical backdrop to Seymour’s voyage was that environmental awareness and ocean activism around the world had blossomed, inspired in part by the famous Blue Planet photo from space, that image of Earth reminding us that ours is primarily a saltwater-ocean planet. The image was the symbol of the first Earth Day in 1970 and part of the “Save the Whales” campaigns. By the end of the 1980s, James Hansen had given his foundational report to the US Congress affirming global warming and the impact of the greenhouse effect, with “99 percent confidence” that human activities were the cause. It made the front page of The New York Times, but did not really shift public opinion. The international maritime community, meanwhile, had expanded its discharge regulations on ships to mandate that no plastic of any kind could be sent overboard.

Thus it was under the radar of environmental campaigns and the higher-profile solo voyages like Lewis’ and Aebi’s that Teddy Seymour breezed along, bound to be the first African American person to sail around the world alone.


Seymour finally just set himself a hard deadline for departure, quit his teaching job, and, after a couple more shakedown trips, sailed toward the sunset, westbound into the Caribbean in February of 1986. He planned to keep in the temperate latitudes and follow the trade winds and the best seasons for the safest weather. Seymour was forty-five, unmarried, and classically handsome with a square jaw, thick moustache, and a runner’s physique.

Teddy Seymour aboard Love Song (c. 1988).

Aboard Love Song, Seymour transited the Panama Canal and stopped in Bora Bora and then American Samoa, where, after seeing a doctor about an infection developed at sea, he finished second in a local running race without having trained in months. He sailed on to Papua New Guinea, to Australia, and then, when others convinced him that it would be too dangerous for an African American person to stop in Cape Town during apartheid—he could not be guaranteed diplomatic protection—he decided to sail up through the Red Sea and the Suez Canal. After stopping in Yemen, Israel, and Egypt, Seymour and Love Song sailed westbound through the Mediterranean in what would be the worst winter in some forty years—the most challenging weather of his entire voyage. He at last escaped beyond the Strait of Gibraltar, and sailed westbound across the Atlantic, riding the trade winds that had shunned Davison a quarter-century before. After a circumnavigation of sixteen months, during which he spent less than $6,000, he returned to the same dock from which he had left. At one point he wrote a short journal-style account, titled “No Frills Circumnavigation,” but he never published this nor did he publish a book of any kind about his voyage. Even among boaty types, his story is barely known.


The elephant in the room of this story of single-handed mariners is that recreational cruising and racing in sailboats has remained mostly a white-male endeavor from the wealthy countries of the global north. Highly skilled small-boat sailors, fishermen, and deep-water adventurers, of all races, ethnicities, and nationalities throughout history, have traveled and worked at sea all over the world. In the modern era, however—due to legacies of colonialism, capitalism, racist elements in publishing, racist economic policies, and the gobbling up of coastal property by primarily white communities—nearly all the early people in the modern era who crossed oceans alone, at least of whom we are aware, were white men, until the likes of Davison, Das, Horie, Adams, and then Teddy Seymour.

I, for example, never sailed in boats while growing up, but came into life on ships after college by getting an off-beat job as an academic teacher aboard for a high-school semester at sea. I had parents who had supported me and allowed me to get a private college education without leaving me in debt. Years later, in preparation for the Atlantic crossing, I bought Fox on my own and arrived in Portugal nearly broke, but I still had a part-time job and a graduate-school scholarship to return to, and my parents to lend me some money to pay off the remaining bills. In other words, I had the means, the ability to take the time off, the financial back-up, and the lack of familial responsibilities to be able to even consider an adventure like this. Although the boat itself, even after all my additions and improvements, still totaled less than a Toyota hatchback, I lived in a town beside the water and in my girlfriend’s apartment while not off at graduate school. I had months off to work on the boat, access to advice, to friends who knew about these things. I could pay to keep the boat in a shipyard and rent a mooring. If my skin were darker, my Judaism more visible, my first language not English, or if I were not a cisgender male, who knows what direct or subtle roadblocks would have been put in front of me—or I might simply have learned growing up that this sort of thing was not for me.

Slocum, Pidgeon, and other well-known single-handers were relatively poor. They did nearly all the work themselves on shoe-string budgets. In the countries they lived in and the ports they visited, though, as white men, even without much money, they had a path to achieve what they wanted if they had the talent and gumption. Any individual and cultural discouragement they felt before departing was but a scratch on the barricades that had been constructed in front of, say, an African American man trying to build a boat and sail around the world in the 1890s, or 1920s, or 1950s—and still today. Maybe Seymour chose to live in St Croix because it was a place at a distance from the racism of America. In one of his rare interviews, with The Bay State Banner (Boston’s African American-focused newspaper) in 1992, Seymour said that going to sea on his own was hardly the most dangerous thing he had ever done. “The easy part was sailing around the world. I’ve almost lost my life on many occasions. I’ve been through Vietnam, I’ve lived in LA where the cops hassled me just because I was a black man running down the streets in a sweat suit.” (Although Seymour said that he never actually said that. This was one of a few early moments that soured him for life on reporters.)

Consider, too, that the nostalgia for the age of sail, of sailing ships, which pervaded much of the Western twentieth-century desire to get away and out to the seemingly unspoiled sea, is not a universal feeling. The ship under sail, the ocean horizon, not even a calm, sandy beach is necessarily soothing and inspiring for everyone. For most Americans the word “yacht” oozes white wealth and exclusion. An ocean voyage in some families might have been the darkest period in their recent or ancestral history. If so, then why would you want to go sailing by yourself to cross an ocean? Nor were the cruising sailors from North America, Britain, and Europe who arrived into ports around the world always, to put it mildly, individuals to be emulated.

Pidgeon and Lewis, for example, saw themselves in the wake of sailing-ship explorers, luffing up into harbors with a colonial privilege to go wherever they wanted. They considered their travels, photographs, and research as benign, even beneficial; Lewis was especially sensitive to treading respectfully, but even he still considered it his right to pursue travel and knowledge and to write and publish his observations of these communities. I am no better.

The idea, however subtle, of the lone white-male colonial sailor as superior and privileged is rooted and germinated in sometimes surprising and even unintentional ways in Western culture. Maurice Sendak’s Where the Wild Things Are, first published in 1963, won the Caldecott Medal and has remained one of the most popular children’s books in English ever crafted. In this picture book a young white boy with dark hair, named Max, wearing a white wolf suit, is misbehaving in his house. He is sent up to his room without dinner by his mother who is not pictured, out of the frame. He is told he’s being a “wild thing.” Max imagines his room transforming into a forest, the walls disappear, and he tromps off as a wolf toward the moon until:

. . . an ocean tumbled by with a private boat for Max

and he sailed off through night and day

and in and out of weeks

and almost over a year

to where the wild things are.

After trying to be brave before an ocean monster, he sails his little wooden sailboat onto a beach. Here Max finds long-haired monsters with yellow eyes and sharp teeth. He tames and impresses the monsters with his ferocity. They crown him “king of all wild things,” have a party, howl at the moon together, and the monsters parade him around on their shoulders as the conquering hero. When Max gets lonely and tired of it all, they plead with him to stay. Max casts off anyway, leaving them sad and disappointed. He sails home alone in his boat until he returns to his room and his warm supper waiting for him. What more could a solo explorer want?

Maurice Sendak, personally and symbolically touched by the Holocaust, a theme in much of his works, surely never intended a colonial message. Yet Max’s single-handed voyage here is nevertheless a privileged solo sailor’s path to exotic pleasures, royal treatment, and then a triumphant, cozy return home with a new appreciation for what he has—not exactly the narrative path of Joseph Campbell’s hero’s journey, but pretty close.

When read today, many of the early single-handed sailing narratives are injected with racist, colonial observations and combative experiences. With his superior sailing skills off Morocco, as he told it, Joshua Slocum outwitted “Moorish pirates,” villains of Mohammed. In the Strait of Magellan, Slocum wrote of the aggression of small groups of Indigenous people, “canoes manned by savages,” some of whom had formed into a criminal band led by a multiracial outlaw named Black Pedro. Slocum reveled in these stories, how he brandished his gun regularly and fired often. Most famously, Slocum described how a group raided his boat one night while he slept. Another captain had given him carpet tacks to spread on the deck, so that when these Native pirates snuck aboard with their bare feet, they shouted in pain and retreated, jumping into the frigid water, making animal-like howls. Slocum, the clever hero, bolted up on deck and fired after them with his rifle. He explained that when going ashore for wood for his stove, he always brought his gun: “I reasoned that I had all about me the greatest danger of the whole voyage—the treachery of cunning savages, for which I must be particularly on the alert.” Once he wrote that he heard the breeze of an arrow whiz past his head and stick into the mast of Spray. Slocum was in real danger in these cases, but as a creature of his time he tangled this up with colonial and technological racism, that all of the world was his domain.

A generation later, Pidgeon was not without racism or judgment, but he defended and was envious of what he believed to be the Pacific Islanders’ unmaterialistic, unhurried way of life. He was far more interested in local people than Slocum, but Pidgeon still maintained a tourist’s distance. He kept on his white shirts and trousers, his camera in hand. He did not begin wearing lava-lavas or tucking flowers behind his ear, as would single-handers like Gerbault or Wray and then Moitessier.

Even as late as the 1960s, Chichester, in Gipsy Moth Circles the World, did not recognize the full story of people in the Pacific: “It took mankind almost the whole of human history to discover how vast the Pacific is—almost to the end of the eighteenth century geographers just couldn’t believe there was so much sea.” Chichester had lived years beside Māori people in New Zealand and must have known of the work of, among others, his fellow single-hander David Lewis, yet for Chichester the mapping of the Pacific began only with Captain Cook.


In “No Frills Circumnavigation,” his brief unpublished account of the voyage transcribed from a few of his at-sea journals, Teddy Seymour reported only good greetings and assistance from the people he met during his twelve port stops. If he encountered racism anywhere he did not write anything about it here. In the months before he died, he sketched out an outline that added more details to his early account. This described gunboats approaching him on both ends of the Suez Canal and officials treating him like a spy in ports in the Middle East. He attributed this more to his U.S. Marines connections than to his skin color. Seymour described enjoying his visits to places such as Darwin and Papua New Guinea and Yemen, where in the 1980s a person of color visiting alone on their cruising yacht, flying the American flag, must have been a novel sight. In his concluding paragraphs to “No Frills Circumnavigation,” Seymour wrote of the kindness of the people that he visited, locals who often treated him “like a long-lost cousin”:

[In the Seychelles] there were invitations to visit homes, eat meals, and be an overnight guest.

One new friend encouraged me to take up residency because all that I could ever want is there, and I agree. Now, that was a place that caused me to sit in the cockpit and sadly observe disappear beyond the horizon . . . I [also later sat] savoring thoughts of the people of Yemen and Egypt, the inhabitants overwhelmed me with goodwill and displayed a keen interest in my journey. It’s usually the man making a living with a fishing boat built on the beach or the guy selling tea on the corner with the homemade cart that is willing to offer the shirt off his back as a gesture of friendship.

I like to imagine Teddy Seymour arriving skillfully in Love Song alone, greeting people with the voice and patience of a schoolteacher and a long-distance runner – how unique and disarming this traveler must have been.

In terms of his what-they-saw, Teddy Seymour’s depiction of his relationship with the ocean has a similar feel to that of Harry Pidgeon. His short account is matter-of-fact, with little drama, and the three-chapter story is written in part to provide information to fellow mariners, outlining, for example, costs and procedures for transiting the two major canals, the Panama and the Suez. In the supplemental outline he wrote late in life, it’s clear that his time in the Marines pervaded his outlook and sense of self-discipline, the value he placed on thorough preparation and logical decision-making. When relating a story about when he had to go aloft in heavy weather to fix his running lights in the shipping lanes, despite his fear of heights, he wrote: “Semper Fi-Do-or-Die sounds great on the parade field. Way out here in the Indian Ocean it means Do & Die.” In the Torres Strait and in his approach to the Red Sea, he was often in waters known for pirates, so he kept a rifle on board and sailed with no lights at night, chewing on coffee beans to stay awake. The problems he described on the voyage were nearly all shore-derived—people, ships, his propeller shaft damaged by a fishing net, how one day off Italy for a few hours he pounded absurdly through seas littered with a patch of floating diapers. Rarely did Seymour write of any significant challenges derived from the ocean itself.

Seymour loved animals his whole life. He wrote that dolphins arrived to keep him calm and safe that day when he had to go aloft. Seymour loved to fish, using seabirds to find them. He was so successful that he often had too much tuna and dolphinfish on board and felt it wasteful, even after he ate fish for every meal for days at a time. When not eating fresh fish, he lived frugally, eating mostly rice and beans, which he reminded the reader is the base food of a majority of the global population.

Seymour’s Love Song was a thirty-five-foot fiberglass design with proven deep-water capabilities, which he had toughened still further with extra layers of fiberglass on the bow. His boat in 1986 did not bristle with the latest and greatest technological developments, but it was still well equipped. He had a production wind-vane self-steering device, which served him well for the entire voyage, requiring only, he said, a little oil each day. He wrote: “no human can outperform the Aries,” which was his wind-vane brand of choice. Seymour had a small electric refrigerator to preserve fresh food on board, and his relationship with his “trusty” engine, a small inboard diesel, was far more favorable than most of his predecessors. His engine got him out of a few potential scrapes, but, at the same time, he was self-deprecating as to its maintenance, joking that he was very good at taking things apart but not as good at putting them back together. In Australia, he needed to bring the engine to a mechanic for repair; it had failed mostly because he wasn’t using it enough. Seymour had wired Love Song with solar panels, a long-distance two-way radio, and he had, with some guilt—because he knew his celestial navigation and practiced it regularly on the voyage—invested in a new satellite navigation set, a Magnavox MX4102, a predecessor to GPS. This device required some repair along the way, and failed at a couple of key moments, but he found the electronic navigation to be enormously helpful, quipping that he would now never leave port without two things: this satellite navigation machine and a solid supply of peanut M & M candy. Seymour also reveled in the technology of the global credit card, allowing him to fix things in port, to “sail now, pay later.”

In the end, Seymour told of a solo circumnavigation that was mostly uneventful—no groundings, no knockdowns, no shark attacks, no rogue waves or typhoons or collisions with ships. Most of the success he attributed to his gear, his boat Love Song, and his careful consideration of the safest route and season for sailing. No spiritual guru like Moitessier or a pioneering salt like Slocum, Seymour wrote like Pidgeon with a military mindset: a sailor with long, earned experience giving the reader the feeling that this was an adventure available to nearly anyone if you respected the preparation necessary and remained vigilant. “If you want guarantees,” he wrote, “buy a toaster.” His ocean was unpredictable but benevolent, a place of beauty and thrill, but never terror. Each day of his voyage the sun rises off the stern and sets off the bow as Love Song circles peacefully westward around the world.

Despite the brevity and practical account of the voyage, Seymour did include in “No Frills Circumnavigation” at least one ecstasy-so-pure moment. During his passage in the Indian Ocean, after transiting the Torres Strait, he was surfing downwind on high seas under full cloud cover, mostly locked up in his cabin with a book while the self-steering did the work. He and his boat were gobbling up the miles in the right direction, in “full stride,” as if running another marathon. He approached Christmas Island where he had planned to stop:

Love Song experienced unbound freedom, surging with the gusts, lifting her transom while sprinting with the swells, as foam rushed alongside the hull and occasionally along the deck, and the song of the bow wave played over and over. We were not alone during those enjoyable days: dolphins were attracted to the sleek hull and playful movement. Those darting, leaping, squealing creatures adopted Love Song as a playmate and devoted many hours, day and night, plowing through the water in concert with the fleeting object, using only a small working jib to answer the call of the strong southeast trade wind. The sensation became captivating, and the experience incomparable. It seemed a pity to curtail all the activity.

So he didn’t. Seymour just kept on playing his Love Song in a “euphoria” right on past Christmas Island, evoking when Slocum sailed right on past the Marquesas. Seymour continued on his runner’s high for another 3,200 miles and three more weeks until finally anchoring at the Seychelles, where he received that warm welcome from the people there, the reminder about what he felt to be most important in life.

Teddy Seymour returned to local fanfare in St Croix. He was featured in a couple of national sailing magazines, received memberships and awards from the likes of the Joshua Slocum Society and the Cruising Club of America, but mostly he returned to his life as it had been in St Croix. He resumed his job as a teacher, still living on his boat. He had three children. He only moved from St Croix in his late seventies for medical care near his daughter in Oregon, intending to go home to St Croix, but he died there at age eighty-one in April of 2023.

While Seymour was on his world voyage in 1986, a librarian and fellow marathon runner named Wallace Williams organized a long-distance running race on St Croix in his friend’s honor. The “Toast to the Captain” race has been held annually ever since, in February, to mark when Seymour embarked on his solo circumnavigation, but also to highlight Black History Month. Seymour was a runner all the way up to his final days. He jogged in his Oregon apartment if it was too cold to go outside. Before he died he wrote that he had had more lives than a cat, because he had escaped thirteen near-death moments—six in Vietnam and seven on boats. The last one was in his early seventies, when he was diving underwater with a snorkel, trying to untangle mooring lines after a hurricane, when he was knocked unconscious and lost four of his front teeth.

Teddy Seymour also totaled that he had lived on a sailboat for fifty-one years of his life.

“He always lived on his boat,” his daughter Maya told me. Her dad kept his final apartment in the same fashion, clean and minimalist.