The Magic of Sailing with a Young Family

Is cruising with a young family the right choice?

October 20, 2021
Top of the mast
After purchasing their Moody 47 sight unseen, a family finds themselves ­cruising the Caribbean, discovering they’re right where they’re suppose to be. Erin Carey

My 4-year-old squealed with delight, the sound muffled by his snorkel. He pointed to the majestic turtle not more than 6 feet away, and I could sense his excitement. I held his tiny hand as we kicked in unison through the gin-clear water, the turtle now within our reach. Gliding past effortlessly, the turtle was completely unperturbed by our presence. Farther on, we noticed two larger turtles peacefully eating seagrass from the ocean bed. We watched from above as my two older sons moved through the water like fish. Diving down several meters, they found themselves almost face-to-face with the impressive creatures. With their mottled shells, leathery skin and kind eyes, these gentle giants were humbling. We felt fortunate to be swimming with them in their natural environment.

Having only just researched the green turtle that morning, it became clear, at that very moment, we had made the best decision of our lives. We were right where we were meant to be. Our home bobbed peacefully at anchor barely 100 meters away, a Moody 47 yacht we had aptly named Roam. The tiny claim we had staked in the beautiful Tobago Cays was perfect. My husband, Dave, was collecting firewood on a nearby deserted beach, his skin tanned and his body toned. That evening we were planning to toast marshmallows under the starry sky. Earlier that day, we had hiked to the small island’s highest peak in bare feet, the rocky ground warm below our still-fragile soles. The view left us almost breathless. Before us was a patchwork of blues: aqua, turquoise, sapphire and azure. We stood there for a long time, taking it all in. There was nowhere else we needed to be. How life had changed from the pandemonium we were used to in the rat race!

Back in Christmas 2015, we were gathered around the dining table in Adelaide, Australia, enjoying lunch with our families. Having recently watched a sailing documentary, it struck us—we were wasting our prime years working jobs we didn’t enjoy and missing out on precious time with our children. It was the wakeup call we’d needed to make a ­crazy decision, and it felt like that moment was the perfect time to share the news. Buzzing with excitement, we cleared our throats in preparation for the announcement, feeling far more nervous than we’d anticipated.


“We have something to tell you guys,” I announced anxiously.

The table fell silent, and my ­sister-in-law joked, “You’re pregnant?”

We laughed, assuring them that we were definitely not having any more children. Taking a deep breath, Dave took the lead. “We’re going to buy a yacht and go sailing around the world,” he said, our faces bright with excitement and anticipation.


Silence fell over the table. Seconds later, the entire family burst into fits of laughter. My sister almost spat out her drink, exclaiming that it was the dumbest idea she had ever heard. “You can’t do that with kids,” one family member said. “You know nothing about sailing,” said another. They stared in disbelief, their eyes as wide as their dinner plates. Feeling deflated, we tried, unsuccessfully, to convince them of our plan.

Two years and two months later, we waved our families goodbye and boarded the plane on a one-way ticket to Grenada. We had purchased our boat, sight unseen, and rented out our Australian home. We had both been fortunate enough to negotiate two years’ leave without pay from our jobs, and we’d saved more money than we ever thought possible. In almost every way, the universe had conspired to help us achieve our dream. We had packed our belongings, painstakingly mulling over every item. Stashed below us in the plane were 10 bags full of boat parts and swimsuits, boardshorts and schoolbooks. The previous two years had flashed by in a blur. Fastening myself into the plane, I breathed a sigh of relief. It was the physical barrier I needed to not only stop me from running in fear, but also to remind me to hold on, sit back, and enjoy the ride. Closing my eyes, I laid my head back, trying to steal a moment to take it all in. The hum of the engine increased, and I braced myself for takeoff, flashing a quick smile across the aisle to my husband and sons as we began our incline.

School days behind a desk and household chores are replaced by sun-kissed days of fishing. Erin Carey

Our arrival in Grenada, the tropical Caribbean island 100 miles north of South America, will remain one of my fondest memories. Almost instantly, we began to fall in love. This sleepy island was a far cry from Adelaide, where the boys had been raised, yet it felt so familiar; it felt like home. With its friendly people and vibrant social scene, Grenada was the perfect introduction to both the Caribbean and cruising life. We spent two and a half months there until we were finally ready to untie the lines and set sail into the great unknown. We were sad to leave our Caribbean dreamland yet excited to discover a new and exhilarating world. Learning as we went, with myriad people willing to help, we soon learned the ropes. Navigating from island to island was like nothing we had ever experienced before. The freedom was intoxicating, our thirst for exploration never quite quenched. Mistakes were made and lessons learned; however, despite the many challenging moments we faced, we never gave up.


Thriving in their new environment, the children flourished in every possible way. We witnessed their mousy-brown hair change into sun-bleached long locks; they barely resembled the militant-looking children they’d left behind. Rarely going more than a week without the company of others, their social skills improved, forming meaningful friendships with other like-minded souls, despite knowing them for only days. Exploring new places together, hand in hand, we would see our family’s bond strengthen and our minds expand. Reveling in each newfound country’s uniqueness, we savored the sights, sounds and smells of these exotic places. We made friends with the locals and experienced their way of life firsthand.

Eighteen months passed by in a blur of sandy feet and salty kisses. Before we knew it, we were leaving the Caribbean and sailing across the Atlantic Ocean. We spent 17 magical days at sea, sailing across the vast blue expanse without a care in the world. Those weeks alone on Roam were blissfully peaceful. The simplicity of life brought everything into focus, away from the distractions of the modern-day world. With absolutely nowhere else to be, we were free to spend our days in a guilt-free utopia, never once feeling bored or scared.

Our safe arrival into the Azores, an archipelago of nine subtropical islands located 900 miles west of Portugal, will remain one of our greatest achievements. We felt unstoppable; if we could cross an ocean as a family, what else were we capable of? Eager to continue living in our bubble, we found ourselves effortlessly falling in love with the laid-back villages, green rolling hills and cobbled streets, the friendly locals, and the affordable cost of living. Weeks turned into months, and the picture-perfect islands wooed us with their charm and sophistication.


However, with the budget dwindling, thoughts soon turned toward home. We left Roam on the hard in Praia da Vitoria, on the island of Terceira, in the Azores. The time had come for us to return to the “real world,” but what was real, and would we still belong?

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Upon returning to Australia, the anxiety hit almost immediately. Having never suffered from it before, we were now overwhelmed by the lifestyle we had left behind only two years prior. We felt like caged animals, trapped in a life where we had little control over what we could do and when we could do it. We were awakened by alarms and told when to eat. Our feet ached from wearing shoes, and we felt exhausted from the endless time spent rushing and racing from one place to the next. Thankfully, the kids slipped effortlessly back into their routines, and their teachers remarked about their maturity and worldliness.

While I enjoyed the conveniences of everyday life—the washing machine and dishwasher, the bathtub and hot ­water—I was now more acutely aware of the environment and the meaning of money. I couldn’t help but find everything to feel wasteful and unnecessary. Our spacious home seemed almost indulgent. I missed the close confines of the boat, the togetherness, and the conversations that flowed because of that. We’d gone from being together 24/7 to seeing each other in fits and spurts between work commitments and obligatory events. Instead of spending our days around ­people living their dreams, we were surrounded by those who didn’t seem to have any dreams at all. Illness and disaster became topics of discussion, and the next tropical island or a storm on the horizon soon became a distant memory.

dinghy sailing
Dinghy ­sailing for this cruising family. Erin Carey

We don’t for one minute regret our decision to cut the ties and sail away with our children. Our family has grown in more ways than we can ever measure. We are far more resilient, and working toward a common goal as a family has shown us our strength. We’ve learned the importance of teamwork, so imperative to the cruising life. While our boys still fight and argue, as all kids do, they also play for hours together in the old-fashioned sense, building forts or shelters, pretending they are still on deserted islands or frolicking in the sea. They pretend to captain their own ships, and indulge in imaginations unleashed since living aboard. They fiercely protect and defend one another, and their bonds are stronger because of the trials and tribulations we encountered together at sea.

Life on the water was challenging in so many ways, yet the benefits far outweighed the struggles. Life was exciting; we felt truly alive, thriving instead of merely surviving, the latter of which so many do. We taught our children the joy of adventure, the rewards of hard work and the benefits of stepping out of your comfort zone. This will forever be a part of their story, of our story, and for that we feel blessed. So, what does the future hold for this family who now find themselves wondering if it was all just a dream? In the words of Oliver Wendell Holmes, “Man’s mind, stretched to a new idea, never goes back to its original dimension.”

We’ve set a date to return to the Azores and continue what we started, to finish crossing the Atlantic Ocean and meander through the Med. Twelve months can’t pass soon enough!

Hailing from the land Down Under, Erin Carey and her family quit the rat race and moved aboard a vessel they bought, sight unseen, on the opposite side of the world. The family returned to Roam in March 2021 and are currently cruising the Med. Follow Erin’s journey on Facebook and Instagram, at Sailing to Roam.


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