Stephen and Estelle have lived onboard longer than on land!

…with Estelle Cockcroft who, with husband Stephen, founded Catamaran Guru. As well as sailing the world they have made a successful business out of their passion educating aspiring sailors to live their dream lifestyle.

AAS: What was the catalyst, back in 1992 in Cape Town, to leave your jobs and become liveaboard boaters cruising the world?

EC: Stephen had always dreamed of circumnavigating the globe in a 45ft sailboat. Embracing this dream before age or health could hinder us, we both agreed to pursue this adventure. Stephen acquired the hull and deck, and we rebuilt and outfitted our 45ft sloop, Royal Salute, in a friend’s backyard. Two years of preparation later, we embarked from Cape Town on what we anticipated to be a two-year sabbatical. Unexpectedly, this sailing journey evolved into a lifelong passion and, surprisingly, led to the creation of our own business.

AAS: What were the biggest challenges in the early days?

EC: I had absolutely no prior experience as a sailor, and my boating knowledge was extremely limited. I relied heavily on Stephen’s expertise and knowledge and, at times, I could not help but feel somewhat ineffectual, and the learning curve was exceptionally steep. Our cruising adventure started in the early nineties in the Indian Ocean.

Although this period remains one of the most magical chapters of our cruising life, it was undeniably the most challenging. Spare parts, medical supplies and most modern conveniences were in short supply. Constantly dealing with boat malfunctions became a recurring nightmare.

While we cherished every moment, we were isolated from friends and family, with only a once-a-month, astronomically expensive five-minute phone call or fax as our means of communication – yes, we relied on faxes back then! Furthermore, we lived on a tight budget, leaving no room for impromptu returns to the mainland for relief. In hindsight, the changes I would have made are to have acquired better sailing skills and ‘easing into’ cruising life in more familiar waters.

AAS: In your many years of travelling you have met some very interesting people and seen history be made. Can you pick out a couple of memorable moments?

EC: We have visited dozens of countries, territories and dependencies during our sailing voyages around the world. The Red Sea with its notoriously bad weather, sandstorms, pirates and the Suez Canal was a milestone achievement journey for us. The diving was spectacular and we visited places like Yemen, Djibuti, Eritrea and Egypt, which were some of the highlights of our journey. Once through the Red Sea, we visited Cyprus and went on to Israel and Lebanon. Our Royal Salute was only the second cruising yacht to visit Jounieh, Lebanon after the end of the 16-year civil war. The country looked like a set in a Steven Spielberg movie… the jewel of the Middle East was a complete wreck! After the initial hostile reception by the military when we arrived in the country (visitors to Lebanon were unheard of and at first we were treated as potential troublemakers), we were delighted with the warm welcome by the people in this country and it was hard to eventually leave when we set sail for Turkey.

AAS: When and how did your life afloat become a business?

EC: Upon our arrival in Kenya, a local friend requested our assistance in conducting dive charters for tourists. Our affinity for people and the lifestyle made this a natural fit, allowing us to replenish our cruising funds. This experience solidified our desire to have our boat sustain its own expenses. In the Caribbean, we encountered numerous people eager to learn how to sail. Consequently, we initiated weeklong liveaboard sailing schools on our own boat. This venture evolved into a business aimed at assisting others in fulfilling their aspirations of boat ownership and sailing, positioning us as a valuable resource for prospective boat owners and sailors.

AAS: How would you describe Catamaran Guru?

EC: Catamaran Guru is a resource and community platform primarily aimed at catamaran owners and enthusiasts. It offers a range of services and information, including boat ownership solutions, sailing schools, boat owner orientation sail and systems training, buying and selling guidance, travel and charter advice and hosting community events. Overall, Catamaran Guru is likely a comprehensive resource for anyone interested in catamarans, whether they are seasoned sailors or new to the world of sailing.

AAS: What are your three top pieces of advice for anyone planning a long voyage or becoming a liveaboard?

EC: Buy the best boat that you can afford, not necessarily the biggest. You do not want a project boat and spend all your time constantly fixing things. Learn how the systems on your boat work and be able to diagnose and fix small problems. It will save you a lot of money and hours of misery. Learn how to sail and make sure that both of you are ‘onboard’ with the plan. If one of you is an unwilling participant, life will be miserable onboard.

AAS: You have seen so much of the world, but where else would you like to visit?

EC: The Pacific is calling our names!

AAS: If you could have dinner with any two people from history, dead or alive, who would you choose?

EC: I would be thrilled to share a meal with Elon Musk, not just because we share South African roots, but because of his extraordinary intellect and vision. He is the visionary who transformed electric vehicles and renewable energy, not to mention the creator of Starlink, which has been a game-changer for nomadic adventurers like myself. Thanks to Starlink, we can sail across the globe while staying connected for work, essentially liberating us to explore without boundaries. I have always been fascinated by the idea of sharing a meal with Ernest Hemingway. His writings are brilliant, but it is his vibrant spirit and passion for the ocean, life and travel that truly inspire me. Throughout our travels, we have encountered numerous places like Cuba, Bimini and Paris, boasting ‘Hemingway was here’. While some of these claims might be more myth than reality, they add a layer of excitement to each visit and connect me deeper to the colourful tapestry of his life.

AAS: Tell us something people might not know about you!

EC: After 30+ years of living aboard I now have lived on a boat longer than I have ever lived on land, yet I still get seasick every time we leave port. It is a lot less pronounced since living on catamarans, but I still get a little queasy on the first day or so out on the ocean. Therefore, I always prep the boat so that everything is stowed and tight and I prep meals so that I do not have to cook. Then I just relax and sleep when I can. After a day or two my body adjusts, and I feel great.
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