A Year at Sea

Imagine trading the bustling energy of New York City for the vast, unpredictable expanse of the open ocean. That's exactly what James Green, known to many as a co-founder of Open Squash, did for a full year with his wife and two young children. His recent “community conversations” talk offered a riveting glimpse into this audacious journey – a year he unequivocally said was "without doubt, the best year I ever had in my life. There's no comparison". 

[Our community conversations series is a great way to get to know your fellow Open Squash members. If you’d like to give a talk, get in touch!]

Yet this wasn't just year of serene sunsets and smooth sailing; it was a saga packed with drama, danger, relentless challenges, and profound personal growth.

James's inspiration for the voyage stemmed from a cherished childhood memory: sailing with his father on a small boat at a pond called Fisher's Green on the outskirts of London. The early connection to sailing planted a seed that would eventually blossom into a transatlantic adventure. While he had sailed since he was a kid and taken courses, James admits he "would not describe myself as the world's best sailor" when embarking on this grand journey. He and his wife, Emma Kate, who didn't sail and got sea sickhad a fear of the sea, bought a large catamaran named Go Bucks, after Milwaukie’s championship-winning basketball team. 

James is not a Bucks fan, and the family quickly decided to rename the boat, eventually settling on Ondine, a name chosen by Emma Kate, after an Italian mermaid fable. James later realized the fable's Ondine murdered her lover for betrayal, but by that point it was too late to rename the boat again. The boat, a 55-foot long, 31-foot-wide catamaran offering about 1,550 square feet of living space, was a significant step up from his previous sailing experience. It’s also a lot bigger than most New York apartments. 

James candidly admits he made a mistake by buying a boat he "loved" the look of, a "fixer-upper," rather than one in excellent condition, leading to having to spend "gobs of money fixing it" later, before eventually reselling it at the end of the journey for a fraction of the cost.

The journey began with an early taste of the sea's unforgiving nature. After sailing the newly acquired boat from Florida to New York, James decided to do an overnight sail to Nantucket. This supposedly "fantastic sail" under a full moon turned harrowing upon arrival. Inside the harbor, meant to be totally protected, a "massive storm" raged with waves breaking over the wall. The wind howled at 50 knots. Trying to pick up a mooring ball in these conditions proved incredibly difficult. As James struggled to keep the large catamaran steady, his wife, Emma Kate, tried to grab the mooring line from the front of the boat. She finally got it, but the line wrapped around her finger, causing a spiral fracture. Despite the gruesome injury, she was initially fueled by adrenaline, proclaiming, "I'm fine!". James knew better, describing the sight of her fingers in disturbing terms. Shore support initially refused to come out due to the danger, relenting only after James sent them a picture of her fingers. James shared his immense admiration for his wife's toughness, noting, "She still has a, yeah, she's a f____g awesome woman". Despite this painful start, she still came sailing for the whole year!

The next ambitious plan was to sail from New York to Bermuda for a squash tournament, connecting James’s sailing life with his squash world. James even hosted a large party in New York with Questlove DJ’ing, before they set out. 

However, a weather map (pictured) showed alarming conditions – "Red and purple is bad. That's like 45 knots of wind," over 50 miles per hour, James said, pointing to the map. Unwilling to expose his wife and kids to such harsh conditions for their first major offshore experience, he flew them to Bermuda and hired a professional crew to sail the boat there. They left New York in a snowstorm.

The journey continued south from Bermuda to Antigua and Barbuda in the Caribbean. James explained that the Caribbean offered easier sailing conditions because the prevailing wind direction made it easy to sail "with the wind always on the beam”This leg marked a significant change: James was now without the professional crew and was joined by his friend David and his teenage daughter. It was Thanksgiving Day, and they were "about as far from anything that you could possibly imagine". Suddenly, the hydraulic steering system broke. James described the terrifying realization: "the boat will only go in circles. All it will do is just go in circle. And I am freaking out, like seriously freaking out." As a novice dealing with his first major offshore crisis without professional help, he had "no idea what to do."

It was Thanksgiving, and no one at the boat yard was picking up the phone. In his panic, he contemplated drastic measures, leaving messages asking, "Shall I abandon the boat? Shall I get on the dinghy and go 350 miles in a dinghy to shore?". Fortunately, he didn't act on that "bad idea." He finally reached someone in Antigua who talked him through how to reset the hydraulic system, which involved depowering, sailing straight using sail trim, and relocking the system. This process had to be repeated "about every eight hours for the remainder of the trip, because there was a leak!". He arrived in Antigua, bought a bottle of champagne for the man who helped him fix the boat remotely, and the trip continued. 

A constant question James faced about the trip was about homeschooling his children, who were 10 and 7 when they started the trip. They initially tried a rigorous morning class schedule based on New York State requirements, but James admits this "fell apart incredibly quickly." Life on a boat is unpredictable; "There are things that happen on the boat and then you have to deal with them and if you're in the middle of teaching a math class, you just have to stop," he said. 

Instead, learning became more project-based and experiential. The kids did a lot of reading and projects. James gave music lessons. A key part of the children’s education was learning about sailing itself. Everyone had a job. James would steer, his wife pulled the halyard to raise the mainsail (using a electric winch), his son would tail the winch, and his daughter, Paloma, was at the mast. Paloma particularly excelled at learning. James shared an example where she gave a presentation on weather forecasting at school after the trip, telling her teacher she learned it by "sailing on my boat." They also learned by exploring the places they visited. Discussions about why Caribbean islands had different colonial histories, and studying local wildlife like bats and turtles were part of their curriculum. His daughter Paloma even learned to cook.

The trip also held deep personal significance and sorrow for James. They spent a substantial amount of time in Dominica, an island he found amazing and one of the few in the Caribbean where indigenous people still live. It was there that he received devastating news: his father got very sick and in due course, died. James flew home just before his father passed to see him one last time. He became visibly emotional recalling this. His father, born in 1920 and a World War II veteran, was a quiet man who had "never really been proud of anything I've done" until James's sailing trip. James learned after going home that his father "had told everyone about my trip," which was "incredibly moving." James felt compelled to take this long trip because his father had always talked about doing one but never did. "And I was like, well, I'm not gonna be that guy," James said, explaining his motivation.

Life on the boat was a constant battle against entropy. James explained that the combination of movement, UV light, and saltwater causes "everything to break all the time". Living on a boat means you are "basically repairing it the whole time." He was responsible for plumbing, electrical, heating, and cooking. He stressed the danger of propane leaks on a boat because the gas is heavier than air and settles low, posing an explosion risk if ignited. He detailed several mishaps in Dominica that delayed their departure. First, he dropped awrench overboard in 30-35 feet of water. He dove in after it, catching it just before it hit the bottom. Coming up, he was "bleeding from my ears and my nose and my eyes were bloodshot," a dramatic sight for his family, all for a "wrench was worth maybe three dollars." The second delay came while repairing the netting at the front of the catamaran. He managed to "stab myself" deeply while splicing the netting — showing a photograph of stitches in his leg. He praised the healthcare in the islands, noting it was "excellent and free," but they had to wait for the stitches to be removed. The third delay was a broken furling system for the main sail. These incidents underscored the relentless nature of boat maintenance.

Even mundane tasks became potential sources of drama. James recounted a stressful moment when his wife decided to cut his hair, and his daughter videoed it. Then, he had to cut his wife’s hair, taking over after she cut the bottom ends off. He admits, "I did not do a good job," but added, "I fixed it, and she still loves me".

After the Caribbean, it was time for the significant Atlantic crossing to Bermuda and then to Europe. James explained that for an Atlantic crossing, they would sail pretty far north, even relative to Nova Scotia. Despite knowing "the time to make a crossing is when the weather is good," James made the ill-advised decision to "leave on my birthday, regardless" – his 49th, entering his 50th year. As soon as they left Bermuda a key part of the mainsail system, broke. James attempted a fix, but after ball bearings went everywhere when he tried to take it apart, he gave up. They had to sail back to Bermuda to get it properly fixed, but still left as soon as it was ready, which meant they "hit some bad weather."

In the middle of the Atlantic, the family faced incredibly rough conditions. James described a 24-hour period where the wind stayed consistently between 40 and 45 knots, and the waves were about 20 feet high. In these conditions, the automatic steering didn't work well going down waves, forcing James to "hand-steer for 24 hours". He faced a "minor mutiny" from the crew because he chose to "keep a lot of sail up and run from the wind." His logic was that sailing away from the wind reduced the apparent wind speed on the boat, lessening stress on the rig. The crew thought he was "nuts" and should "hove to" (stop the boat) or reduce sail. James maintained he was right, and they were fine. Safety offshore was paramount. James explained how he and the crew wore life vests that inflated on contact with water and that they were "clipped in the whole time" during the crossing, attaching themselves physically to the boat.

The most terrifying moment came shortly after the storm subsided. Brett Erasmus, a large, tough South African friend on the crew, was on watch. After James had finally managed to get some sleep, Brett woke him up at dawn, looking "pale as a sheet, like terrified". Brett simply said, "James, you have to get up... you have to come and take a look". What James saw was a "massive water spout" off the port bow. He couldn't judge the distance or size because of the low-light conditions, and the radar hadn't picked it up. He immediately told Brett, "it's there,” pointing to where it was, and then pointed around it, saying, “go that way." James deeply regretted not taking a picture of the phenomenon. He later realized the significance of it being dawn – "to that point, a little before, he wouldn't have seen it". James emphasized the danger: "A water spout is a tornado in the water. It would have killed us all," he said. 

They eventually made it to the Azores, still 1,000 miles from Gibraltar. James mentioned the lovely tradition in the Azores where arriving boats paint something about their voyage on the dock. Ondine's painting included whales and dolphins they saw, with a dolphin for each crew member. As they neared the coast of Portugal, they were boarded by the Portuguese Coast Guard. They asked for James's “license.” This presented a problem: at the time, licenses were often granted only to nationals, and James wasn't a US citizen yet. He hadn't gotten an English license either. His solution? He "showed them my New York driver's license," which somehow sufficed.

Arriving in Gibraltar proved equally eventful. James expected it to be incredibly busy, but found "no one." Arriving at dawn again, they were told to "get out!" over the radio. It turned out someone welding on a full oil depot caused an explosion, leaving "oil everywhere". They had to dock in Spain instead. James also shared a peculiar local sight: the airport runway is across the entire island, and people walk or drive across the tarmac to enter Gibraltar from Spain, stopping only when a plane is landing.

Sailing through the Mediterranean brought its own mix of beauty and peril. They visited Formentera, Italy, and Greece. James loved the spontaneity the boat allowed, recounting pulling into a small Italian island called Ustica where they docked tightly with local boats, went to restaurants, and simply left without hassle – "It's the Italian way," as one audience member observed. Another dramatic incident occurred near Stromboli, a famous volcano. While anchored and planning to hike up, James noticed the weather picking up rapidly. He instinctively canceled the hike and rushed everyone back to the boat. Although the waves hadn't built up yet, the wind was so strong he couldn't release the mooring buoy and had to "cut us off" to sail away. He saw another boat that stayed behind, swept onto the rocks.

In Zakynthos, Greece, James noticed something wasn't right with the boat's handling, especially under power. He decided to inspect the hull. A pop quiz moment in his talk revealed the shocking discovery: the boat's rudder was missing. "Correct, there's no rudder on that hull. We think we had sailed about 5,000 miles with one rudder," he said, pointing to where a rudder should have been. The propeller shaft had also separated. James believed this damage likely occurred during the Atlantic storm. Despite sometimes veering off course, he hadn't realized the severity of the damage as a catamaran has two large rudders

The trip was drawing to a close, partly due to the significant expense – the "main expense" being the boat and its endless repairs. James was beginning to interview for jobs back home. During a sail to Naxos, Greece, while James was below deck studying for interviews, an unexpected wind shift caused an "accidental jibe." James explained this is "a very bad thing in a boat. It's the most dangerous thing that you can do". Reacting quickly, he rushed out but, wearing a baseball cap that obscured his upward vision, and ran straight into the metal frame of the cabin entrance. He was knocked unconscious and woke up bleeding heavily from his head. He called his wife, who took one look and turned pale. He got a concussion and required 20 stitches.

The final, dramatic incident of the trip occurred while anchored in Naxos. James had flown back for interviews, leaving his wife, kids, and a friend, Cindy, who was not a sailor, on the boat. The wind blew up, and the anchor failed. The boat started drifting out to sea. James received frantic texts and calls upon landing, learning about the ordeal his wife faced alone with the two kids and non-sailing friend. One engine wasn't working. Emma Kate managed to start the working engine, pull the boat back towards shore, call the Coast Guard (who deemed her "doing just fine" despite her distress), re-anchor the boat, all while a Greek tanker offered distant assistance. Just as the anchor held, the lines from the boat wrapped around the propeller, killing the working engine. James arrived to find his wife safe after this remarkable display of resilience. He said: "That is still one of the most remarkable things that she's done. I mean, just incredible. She did an amazing job".

The year-long adventure concluded in Didim, Turkey, where they pulled the boat out of the water and James eventually sold Ondine. Reflecting on the journey during job interviews, James initially struggled to articulate what he gained. He asked his daughter Paloma, who simply replied, "I got to know you, Daddy,” and that was it. This simple answer resonated deeply, highlighting the profound connection and understanding forged within the family during their intense year together.

Looking back, James acknowledges things he would do differently, primarily regarding the boat. He would buy a boat built specifically for such extensive cruising and ensure it had "no known problems." The catamaran he chose was originally designed for more local cruising, like around the British Virgin Islands. He compared taking Ondine on their journey to taking a family minivan across the Mojave Desert. The experience, however, turned him into a highly capable boat repairman: "I have now learned how to fix everything. I can fix anything on a boat," he said – from engines and fiberglass to replacing sewage tanks. He learned by hiring professionals to work alongside them.

Despite the isolation of the sea, James found a vibrant community in many places they stopped, particularly in the Caribbean. VHF radio channels served as a daily hub for boats to connect, share information, and organize social activities. His wife, a yoga teacher, would announce beach yoga classes. The kids made lifelong friends with other cruising families.

Addressing the inherent risks, James noted that "99% of sailing accidents happen within a 20 miles of shore," often due to fatigue, bad weather, and hitting things. He cited the incident in Naxos where his wife was blown out to sea as being more dangerous than the offshore storms because of the risk of hitting rocks. Offshore dangers include hitting whales (a friend's boat sank after doing so) and rogue waves. While he doesn't believe their older radar would have detected the massive water spout they saw, modern radar would.

Ultimately, James’s year at sea was far from a luxurious cruise. It was a crucible of challenge, forcing him and his family to confront fear, overcome adversity, and rely on each other in ways they never had before. 

James admitted that he possesses a very high tolerance for risk, likening it to his work in startup businesses. He said that unless he genuinely believes he is going to die, he considers the situation "fine". This is evident in his choices during the sailing trip, such as deciding to leave Bermuda for the Atlantic crossing on his birthday despite unfavorable weather, which he acknowledged was an "incredibly bad idea". On his marriage to Emma Kate, it appears remarkably resilient. He attributes the strength of their marriage, which reaches its 25th anniversary in June this year , to his wife's acceptance of who he is, including his independent nature and high tolerance for risk. He explains there were "no secrets," she knew he wanted to do this, and she loves him for who he is, preventing blame during challenging situations.

When James got off the boat, he weighed 175 pounds and felt he was in "crazy good shape" due to the constant movement on the boat. He felt "right on his feet" and "good" upon his return. He mentioned that he played squash "almost right away" and that it felt "fantastic" initially. However, this state of fitness did not last. He notes that he "seriously saw it" deteriorate just "two weeks later" after that initial fantastic feeling on the court. “Three weeks later, I sucked," he said. This rapid decline coincided with a significant weight gain; he gained 20 pounds in just two weeks after getting off the boat. He jokes about the impact of carrying that extra weight around the squash court.

The trip was expensive and nearly broke the family physically and financially. But it was also the best year of James’s life, a testament to the resilience of the human spirit and the profound bonds of family forged in the most demanding of environments. James’s story is a powerful reminder that sometimes, the most valuable discoveries are made when you dare to venture far beyond the familiar horizon.