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We Quit Our Jobs to Go Sailing Around the World

We all know what it feels like to be wake up early on a particularly grey and cold weekday morning and feeling absolutely miserable. For most of us, leisurely time in a warm climate or a sailing holiday are treats that we can enjoy only once a year. It is, therefore, no wonder that we like so much reading stories about people who have traded grey mornings with clear blue skies and crystalline waters.  Join us as we experience the all-year-round boating lifestyle vicariously through the accounts of these free-spirited sailors.

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Karl Gerchow and Conner Esworthy

Karl Gerchow and Conner Esworthy sailing

Source: Conde Nast Traveller

Karl Gerchow and Conner Esworthy had always dreamt of leaving their jobs and go sailing instead but were always hesitant to go for it. This all changed when they came across a practically new cruising sailboat for sale and soon after decided that the time was right to leave everything behind and embark on their journey. Both Karl and Conner admit that they were modest sailors and that their sailing experience was only limited to a few sailing trips in Turkey, Panama, and Grenada. So, their sailing adventure is as much about learning from the more experienced sailors that they meet as it is about discovering new places. The couple claims that sailing without time constraints has enabled them to leave their itinerary open-ended and make up their travel plans as they go along…not bad at all.

Victoria Fine

victoria fine sail woman


While most of us are busy juggling one hundred and one constraints on a daily basis, Victoria Fine’s life is only dictated by the wind and the sun. In one fell swoop, Victoria left a high-profile job, started her own business, and set sail together with her husband. It is, therefore, no coincidence that she only needs one word to describe her life and that word is “freedom”. Living on a boat has enabled Victoria to set sail to any destination that suits her fancy, live simply, and feel closer to nature. Professionally, Victoria is working fewer hours, according to a self-dictated schedule, and all this while earning twice as much money than what she earned a salaried media executive. Now that’s one lucky lady.

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Andrew Stephens  

Andrew Stephens sailor catching a marlin

Source: Everett Herald

Andrew Stephens had been working in the financial sector when he was offered a very substantial bonus in exchange for a contractual commitment. This prompted him to think about his choices and what he wanted out life. So, the next day, Andrew shocked his co-workers when he told them that he was setting sail instead of signing up. Sailing solo means that Andrew is constantly learning new skills and getting to grips with his ability to cope with challenging situations. Anyone would agree that this is in itself a very gratifying experience but the feel-good factor does not stop here. Indeed, Andrew goes on to describe the spectacular sunsets that he gets to experience every day, the remote islands where people live harmoniously, and the overall feeling that there is more to life than cars, houses, and money. We couldn’t agree more.

It may seem like these sailors are on a perennial sailing holiday but we would be remiss if we did not point out that this lifestyle has its challenges too and certain comforts that we take for granted are not available on a boat (or at least that’s what we tell ourselves on those miserably gray weekday mornings).

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