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 they’ve never done it before. They set off almost immediately on major passages, heading deep into places like the South Pacific after crossing an ocean. It makes for very compelling content, but sometimes it feels like you’re watching a potential train wreck unfold.
Viewers, many of whom are fascinated by the lifestyle and have a desire to sail around the world, see these stories and draw their own conclusions. Watching people with little to no experience cross oceans and make it to places like Tahiti creates a sense of hope that they can do the same. And in many ways, they can—but the problem is that it also creates a false sense of security. That
narrative, often amplified on YouTube, can be misleading. It downplays the level of preparation and knowledge required, and in reality, it can be dangerous and unwise to approach offshore sailing that way.
But from a seamanship standpoint, it’s not a model to follow. What often isn’t visible is the level of risk involved when fundamental knowledge is missing. The reality is, many of those situations rely heavily on favorable conditions and a degree of luck.
Then there’s another group—people who take the time to study, learn, and build their skills before heading offshore. They approach it differently. They understand that success in offshore sailing isn’t just about getting out there—it’s about being prepared for what happens once you do. That difference, in many cases, determines whether the experience becomes sustainable or short-lived.
There is, of course, a certain level of “figuring it out as you go,” and that’s completely normal. Some things simply can’t be learned from a book—you have to experience them. Offshore sailing will teach you lessons in real time, and that’s part of the process. But the issue isn’t learning along the way—the issue is skipping the fundamentals that are entirely within your control before you ever leave the dock.
What I’m talking about is a lack of preparation in the basics. A thorough understanding of your own boat—how
it sails, how its systems function, how to operate and troubleshoot them, and how your safety equipment actually works. These are not advanced concepts; they fall squarely under good seamanship. And yet, they’re often overlooked. There’s a level of preparation and forethought that has to go into a vessel before you take it offshore or commit to a long passage. Once you’re far enough out, you are truly on your own. Assistance, if it comes at all, can take days. At that point, you and your crew are the plan.
You will absolutely continue learning as you go—that never stops. But there’s no substitute for being prepared before you leave. The more you understand, the more self-sufficient you become, and the better equipped you are to handle whatever the ocean puts in front of you.
Where People Get It Wrong
Where people get it wrong isn’t in the idea of learning as they go—that’s part of the process. Everyone does that.
The problem is skipping the preparation and failing to build the skills that can and should be learned before ever heading offshore.
Too often, the focus is placed on the wrong things. People worry about buying a boat, chasing the lifestyle, and getting out there as quickly as possible. Many have never actually been on a bluewater cruising sailboat. They’ve
never done any extended cruising, and they skip the fundamentals that actually keep them safe and capable. In my opinion, there’s far too much emphasis placed on “figuring it out as you go,” when more emphasis should be placed on learning and building skills before you even purchase a vessel and leave.
There’s also a tendency to underestimate what offshore sailing really demands. Once you leave the coast behind, there is no easy fallback. You are responsible for the vessel, for the crew, and for every decision that gets made. Help, if it’s needed, may not arrive quickly. That reality changes everything.
The gap isn’t in ambition—it’s in preparation and skill level. The difference between those who continue and those who turn back—or quit sailing altogether—often comes down to how well they understand what they’re getting into before they leave, and how prepared they are to handle it.
What It Actually Takes
What it actually takes to sail offshore—and ultimately sail around the world—comes down to one core idea: seamanship. And seamanship is not one skill. It’s a collection of many skills that all work together.
It starts with a foundation. That foundation is seamanship
—a broad and interconnected set of skills that includes
how you handle a vessel, how you understand and manage its systems, how you interpret weather, navigate, provision, and make decisions offshore. These aren’t separate disciplines; they’re all part of the same skill set. And weaknesses in any one area tend to show up at the worst possible time.
The Reality Offshore
The reality offshore—assuming you are well prepared and have developed solid seamanship skills—is that there is nothing quite like it. It’s hard to describe unless you’ve experienced it, but it’s one of the most rewarding things you can do.
There’s a level of confidence that comes from knowing you’re prepared. You understand your boat. You understand the conditions around you. And when situations arise—whether it’s changing weather, sea state, or a system that needs attention—you’re able to handle them. You’re not guessing because you have the skills to make the correct decision.
That confidence doesn’t come from luck. It comes from time, effort, and experience. It comes from putting in the work ahead of time and building the skills required to operate safely and effectively offshore.
And with that comes a real sense of accomplishment. Sailing hundreds, even thousands of miles, arriving
somewhere under your own command, and exploring a place by boat—it’s something most people never experience.
What makes it even more meaningful is the connection it creates to the history of sailing itself. You begin to realize that what you’re doing isn’t new—you’re participating in something that has been done for centuries. The decision-making, the reliance on skill and seamanship—these are the same fundamentals that sailors have depended on long before modern technology existed.
They explored the world for the first time, often with limited information, relying on skill, crew work, and experience. That’s true seamanship. You’re part of a long history of people who have crossed oceans and explored the world under sail. There’s a real sense of gratitude and respect for those early sailors who charted unknown waters, often under far more difficult conditions, making it possible for those who follow to sail them more safely.
Closing Thoughts
In the end, the right way to explore the world under sail starts with learning. And interestingly enough, learning how to sail is often the easiest part of the entire equation.
The deeper work comes in building true seamanship—understanding blue water cruising boats, their complex onboard systems, and how to operate and manage them
safely and effectively in a wide range of conditions. Choosing the right boat takes time and experience. The more time you spend on different vessels, and the more you study and research different blue water boat designs, the more you refine your understanding of what works, what doesn’t, and what truly matters offshore. That process can be expedited by learning on a true bluewater cruising boat, like the Amel Super Maramu 2000.
From there, everything starts to come together. You gain confidence. You become more self-sufficient. And eventually, you put yourself in a position to go out and explore—whether that’s coastal cruising or crossing oceans.
And that’s where the reward is.
Exploring the world under sail connects you to nature, to history, and to a way of living that’s difficult to replicate anywhere else. Along the way, you meet others who are doing the same thing. You learn from them—sometimes from what they’ve done right, sometimes from what they’ve done wrong. You build friendships. You become part of a community that shares a common mindset.
It’s not always easy. There are challenges. But the majority of the time, it’s incredibly rewarding.
This is ultimately why I started One World Sailing Academy—not to sell a dream, but to help people achieve
it in the best possible way. By building the skills, the knowledge, and the confidence required, you put yourself in a position to truly enjoy this lifestyle and everything it has to offer.
Because when it’s done right, there’s nothing else like it