What It Really Takes to Sail Around the World (And Why Many People Get It Wrong)
Over the past several years, there has been an explosion of interest in bluewater cruising and the idea of exploring the world under sail. In my view, this shift started well before the pandemic and was then accelerated by it, as people began to question traditional routines and seriously consider alternative lifestyles. The conventional path—steady job, predictable routine, weekends off, a couple weeks of vacation each year, buying a home, building a career and family—was once deeply appealing. After periods of global instability like World War II, people longed for structure, security, and normalcy, and that lifestyle delivered exactly that. But in modern times, that same structure can feel very different. What was once seen as stability can now feel unchallenging, predictable, and, for many, disconnected from any sense of adventure or meaning—often far removed from nature, especially in urban environments. This is, of course, a matter of perspective, but it’s one I hear more and more often. People start asking themselves simple but important questions: Why am I doing this? What is the point? There’s a growing sense that you can follow that path for decades, only to arrive at the end of it with limited time and energy left to actually enjoy life on your own terms. There’s been a growing hunger for something different—something more flexible, something with more meaning. For many, it’s a pull that’s hard to clearly define. It’s a desire to reconnect with nature, whether that’s the ocean, the mountains, or remote stretches of coastline. It’s a deeper connection to the world around you—something more powerful, and for some, even spiritual in nature. At the same time, there’s a large community of retired sailors who followed that traditional path for decades and are now out cruising. When you talk to them, you tend to hear the same thing over and over again—they’re happy they made it happen, but many of them waited 20 or 30 years to finally do what they had always wanted to do. I’ve seen it firsthand, and I’m not immune to it myself. For a long time, the reality was that making a living while sailing full-time was extremely difficult. The structure of society didn’t really support it. You had to build your life first, and then maybe—later—you could go. There is a big shift happening now toward alternative lifestyles. Technology like Starlink has made it possible to stay connected from almost anywhere in the world, and social media has opened the door for some people to actually earn a living while traveling. The rise of remote work and what are now commonly called digital nomads has made a lifestyle that once seemed unrealistic far more attainable. At the same time, YouTube has played a major role in this shift. Channels like SV Delos and Sailing La Vagabonde, among many others, not only gave people a front-row seat to life at sea, but also proved that it was possible to monetize that lifestyle. That realization changed everything. It showed that you didn’t necessarily have to wait decades to go—you could build a life around it in real time. As a result, there’s been a massive explosion of sailing channels with large audiences, and many of those viewers are now attempting to follow a similar path. And underneath all of that is something deeper—a very human desire to wander, to explore, and to see the world as we did for hundreds, if not thousands, of years. But for most people, that desire gets buried. Society lays out a path, and it’s easy to follow because it’s structured, familiar, and constantly reinforced with a false sense of security. At every stage—school, career, family, house, retirement—you’re told what comes next, and if you stay on that track, you’re considered successful, often judged primarily by financial success. Perspectives outside of that framework aren’t always part of the conversation, and it leaves very little room to question whether the path you’re on is actually what you want. In the blue water cruising community, success is defined very differently. It’s rooted in experiences, memories, friendships, and the kind of adventures that stay with you for a lifetime. Over time, the traditional path becomes the default. Stepping outside of it starts to feel risky, unrealistic, or even irresponsible. Before long, the idea of doing something different—like sailing around the world—gets pushed further and further into the background. Not because the desire isn’t there, but because it’s easier to keep moving forward on the path that’s already in front of you than it is to step off and figure out something entirely different. What People Think It Takes to Sail Around the World When people start thinking about sailing around the world, the romantic picture they have in their head is almost always the same. It’s calm anchorages, clear water, quiet sunsets, and the freedom to go wherever and whenever you want. It’s stepping away from the noise and routine of everyday life and replacing it with something simpler, more peaceful, adventurous, and meaningful. There’s truth in that. Those moments absolutely exist and frequently happen. But what often gets overlooked is everything that needs to be learned to accomplish this vision. A lot of people assume that if they can just get the right boat, the right gear, and enough money, they can figure the rest out along the way. But the reality is, many don’t yet have the experience to even know what the “right” boat or equipment actually is. I see people buying coastal cruising boats and trying to turn them into bluewater boats. Boats get outfitted based on assumptions rather than real experience, and priorities shift quickly. Especially in the early stages, what feels like a solid decision can change completely within a year, simply from gaining a better understanding of how boats, systems, and real-world sailing actually work. There’s a common narrative you see online—people buying boats, completing minimal preparation, all with no real understanding of what actually needs to be done because