Around the World with Oliver: A Sailor’s Tale of Discovery

In an era dominated by instant gratification and high-speed travel, one man chose a different path—slow, deliberate, and guided by the wind. Oliver Stanton, a self-taught sailor from Devon, England, embarked on a solo circumnavigation of the globe not for fame, fortune, or followers, but for something much deeper: discovery.

Over three and a half years, Oliver’s journey aboard his humble 38-foot sailboat Seawind became a tale of human curiosity, quiet courage, and the enduring relationship between man and the sea. Around the World with Oliver: A Sailor’s Tale of Discovery is not just about oceans crossed, but lessons learned, cultures embraced, and the vast inner voyage that unfolded along the way.

The First Step: Leaving the Familiar

For Oliver, sailing was never just a hobby—it was a calling. Having spent years reading the works of Joshua Slocum and Bernard Moitessier, his imagination was stirred by the idea of setting sail and leaving the predictable shores of modern life behind.

By 2020, after years of planning, saving, and restoring his beloved vessel, Oliver set sail from Plymouth. The first few days were filled with excitement and anxiety in equal measure. “When land disappeared behind me, I felt both terrified and completely alive,” he wrote in his log. That was the beginning of a journey that would test every ounce of his resolve.

The Atlantic: Baptism by Ocean

Crossing the Atlantic was Oliver’s first major challenge. From the Canary Islands to the Caribbean, he spent nearly three weeks at sea alone. With no engine for long-distance propulsion and relying solely on sail and self-steering gear, Oliver was at the mercy of the wind and waves.

He faced sleepless nights, blisters from hauling lines, and a snapped halyard that nearly sent him adrift. Yet, he also witnessed skies so full of stars they felt like galaxies pouring into his boat, and dolphins that danced off the bow like old friends. “The ocean humbles you,” he later said. “It strips away everything unimportant.”

Caribbean Wonders and Human Connection

When he arrived in the Caribbean, Oliver was not met with grandeur, but with the warmth of island hospitality. In Saint Lucia, he was invited by a local family for Christmas dinner. In Grenada, he helped repair storm-damaged fishing boats in exchange for supplies.

Rather than rushing from one port to another, Oliver took time to connect—learning bits of Patois, trying local dishes, and hearing the stories of other seafarers and locals alike. “Discovery isn’t only about geography,” he reflected, “it’s about people.”

Canal of Dreams: Crossing into the Pacific

Sailing to Panama, Oliver encountered the next major milestone: the Panama Canal. For a small sailboat, the canal can be intimidating—towering cargo ships, tight schedules, and bureaucratic red tape. But with the help of fellow cruisers and a local line handler named Ricardo, Oliver successfully transited the canal in January 2022.

As the lock doors opened and the Pacific stretched out before him, Oliver realized: this wasn’t just a journey around the world—it was a journey inward. The biggest discoveries, he began to suspect, were yet to come.

The Pacific: Beauty, Vastness, and Solitude

The Pacific leg was the longest and most mentally challenging. For 29 days, Oliver sailed solo from Panama to the Marquesas. There were days of blissful calm and others when storms battered Seawind for hours. His journal entries during this time reflect the psychological toll of solitude: “I talk to the boat now, like a friend. She doesn’t answer, but I feel her listening.”

Yet, there was wonder, too. He marveled at the bioluminescence in his wake and the silence so complete it felt sacred. In the Marquesas, he rested, reconnected with civilization, and explored verdant mountains and forgotten trails.

From there, he slowly island-hopped through the South Pacific—Tuamotu, Tahiti, Tonga, and Fiji—each island offering its own discoveries in culture, cuisine, and community. In Tonga, he spent weeks helping with cyclone relief and formed bonds with villagers that would last a lifetime.

South to New Zealand: Learning to Let Go

Reaching New Zealand was a spiritual moment for Oliver. Not only had he crossed the world’s largest ocean, but he also arrived at a place he had dreamed of since childhood.

He spent five months there, working part-time at a marina to earn funds and soaking in the unique blend of Maori culture and natural beauty. More than just a resting point, New Zealand marked a shift in Oliver’s mindset. He realized he no longer felt the need to "complete" the voyage to prove something. “Discovery isn’t about finishing a race,” he wrote. “It’s about how deeply you experience the places you go.”

Indian Ocean Trials and Triumphs

The next challenge was the Indian Ocean, and it tested Oliver more than any previous leg. Sailing from Australia to Madagascar via the Cocos Islands and Mauritius, he encountered rough seas, gear failures, and growing fatigue.

But there were golden moments: swimming with whale sharks, watching fireflies drift across the water at night, and seeing the Southern Cross gleam above the horizon.

In Madagascar, he immersed himself in a world vastly different from his own. He visited remote villages, learned about deforestation from local conservationists, and saw firsthand how climate change was affecting coastal communities. His perspective on sailing as a privilege—and responsibility—deepened.

Africa and the Call of Home

Sailing up the African coast to South Africa brought new revelations. He explored Cape Town, met Zulu sailors who shared oral histories of sea voyaging, and survived the treacherous rounding of the Cape of Good Hope—a rite of passage for any circumnavigator.

But more than that, Africa reminded him of home. The smells of open fires, the laughter of children playing by the water—it stirred memories of his early days on the Devon coast. Discovery, he realized, also includes rediscovering what you already know.

The Atlantic Revisited and Full Circle

Oliver’s return across the Atlantic—from Namibia to Brazil, and then via Cape Verde back to Europe—was quieter, more reflective. He was no longer chasing miles or checking countries off a list. Instead, he sought places where he could simply be present.

He spent time in small Brazilian coastal villages, writing, drawing, and teaching local children about sailing. When he finally returned to Plymouth in late 2024, it wasn’t a triumphant homecoming, but a peaceful return.

“I left to discover the world,” he said upon arrival. “And I found it—not in landmarks, but in moments.”

What the Sea Taught Oliver

Over 45,000 nautical miles, Oliver discovered:

• Patience – The wind does not answer to your plans.

• Resilience – Storms pass, but the lessons remain.

• Humility – The sea does not care who you are, only how you sail.

• Gratitude – For every sunrise, every helping hand, every safe harbor.

• Interconnection – That people, from Tonga to Tunisia, are more alike than they are different.

Legacy and Ongoing Impact

Oliver’s voyage was documented through a modest blog, Sailing With Soul, which grew a loyal following of readers inspired by his vulnerability and poetic insights. He didn’t seek virality—but he found resonance. Teachers used his stories in geography lessons. Young sailors wrote asking for advice. Environmental groups cited his firsthand accounts of reef bleaching and plastic pollution.

Now back on land, Oliver continues to write, lecture, and consult with ocean conservation projects. He’s working on a book that blends memoir, travelogue, and philosophy—much like his voyage itself.

Final Reflections: A Sailor’s Tale of Discovery

Around the world, through typhoons and trade winds, island harbors and vast lonely stretches, Oliver’s story is not just one of adventure—but of intention. It’s about slowing down to see the world with new eyes. To choose curiosity over fear. To let nature be your teacher and people your compass.

In a society so focused on arrival, Oliver reminds us of the joy and necessity of the journey. His story isn’t finished—it simply returned to port. But like all great tales of discovery, it now sails in the hearts of those it has touched.