Everything You Need To Sail Around the World and Earn Money While Doing It

Have you ever wondered what it would be like to leave everything behind and sail your own boat around the world? For those who take the leap, it’s almost guaranteed to be the greatest adventure of their lives.

The first time I cast off my dock lines to sail across an ocean, I soon realized that I had discovered the purest form of freedom available to anyone in the modern world. If you hate being stuck in the rat race, and want to experience adventure, exotic foreign cultures, and unspoiled natural beauty every day, there is no greater goal than to sail around the world on your own boat. 

More than a decade later, I still feel the same way. There is something unique about sailing across the oceans on a small vessel that you can’t find in any other mode of travel.

You can’t find it on a world cruise, locked up on a giant ship with 5,000 other passengers, nor can you find it with a round-the-world flight ticket and a passport full of 24-hour transit visas. By sailing your own vessel around the world, you are free to travel any direction on the compass, any time you like without lugging around a heavy suitcase or subjecting yourself to long lines at the terminal. 

But that incredible liberating freedom comes with a large dose of responsibility and risk. After all, those postcard-perfect beaches and remote islands don’t come without a price of their own. 

Not Everyone Can or Should Sail Around the World

When I first decided to pack up and sail around the world, I was full of teenage optimism but did not yet fully understood all of the challenges associated with sailing around the world. Today, with almost 30 years of sailing experience and over 65,000 nautical miles under my keel, I have an all too real understanding of what it takes to sail around the world. I wrote this guide to share that knowledge with you. 

If you are looking for a guide that tells you that anyone can sail around the world no matter what, then this isn’t the guide for you. The reality is that the lifestyle is not for everyone.

What I will tell you is that if you really love sailing on the ocean, and are willing to put in years of hard work and sacrifice, and if you are lucky enough to have the ability to accumulate the resources that the average person would need to buy their own house or start their own successful business, then yes, you have a good shot at being able to sail around the world. 

In the sailing community, there is a whole industry of sailing celebrities and inspirational speakers that fill lecture halls and go on TV to share the message that anyone can sail around the world and that you can achieve anything if you simply want it badly enough. And, while it’s very important to have inspiring people to look up to, the harsh reality is that their messaging is very dangerous.

The truth is that sailing around the world is not an easy thing to do, and it’s not a good idea for every person to give it a try. Very likely it will be the most difficult thing that you have ever attempted to do. Sailing around the world takes years (sometimes decades) of hard work, and there is a very real level of risk and danger that somehow gets left out of these sailing celebrities’ speeches. 

Sealife Fantasy

For many people, the thought of circumnavigating brings to mind images of drinking Pina Coladas from the cockpit at sundown while anchored up in a perfect south seas atoll and watching island girls dance in front of raging bonfires on the beach. People dream of wearing nothing but a swimsuit for weeks on end and diving from their own boat to spear fresh seafood for dinner. 

These images can be a very real benefit of the world cruising lifestyle and circumnavigating on your own boat will indeed give you a taste of paradise that few people get to experience this side of heaven. But, there is another side of the story that is often overlooked by “YouTube sailors” and boating celebrities. 

The reality is saving enough funds to buy and equip your own vessel for the voyage and maintain it along the way. It means sailing 30,000 nautical miles across the ocean and spending almost a year at sea away from the sight of the shore. It means taking on risks like being run down by a ship and being prepared to survive a serious storm at sea or an unexpected medical emergency thousands of miles away from the nearest hospital. It may mean spending weeks without a hot shower or a washer and dryer, away from an internet connection and Netflix, and living without most of the conveniences we take for granted in the 21st century. 

And, most importantly, for those who aren’t independently wealthy, it means finding a way to make a living from the remote corners of the planet. The good news is that now it is more feasible than ever to earn a living remotely while sailing around the world.

In this guide, I will teach you what it takes to sail around the world and support yourself along the way, even if you weren’t born rich. 

When you choose to live on the water, you will challenge yourself every day. You will wake up in a new place from one week to the next and face new challenges constantly. The nature of the lifestyle will force you to be both physically and mentally active every day. You can choose where you want to go, when you want to go there, and use your own talents to harness the wind and currents to get you there.

Every minute, you will be responsible for the decisions that will keep you and your crew safe. Sometimes simple things that you didn’t even have to think about in your previous life will be great challenges, like finding freshwater or figuring out how to do the laundry or find fuel for the stove. 

I will also tell you that if you are successful, then the rewards will be well worth it. I have never heard of someone returning from a circumnavigation of the planet and telling their loved ones that they really wish they had stayed home and kept their old 9 to 5. 

Sea Lifestyle

The reward for all the hard work and risk is a lifestyle unlike any other. By living on a boat, you can travel anywhere in the world that is connected to the sea and take your home along with you. You can anchor for free in front of the most pristine beaches in the world and spend a month or two tied up to your own personal uninhabited island in the South Pacific, if you like. You can choose one of ten million coves to make your backyard for the night. You can visit all kinds of places that to most people are just names on a map, places like Bora Bora and Brazil and the Seychelles Islands. World cruisers are some of the last people in the world who get to spend much of their lives on the ocean.

“The [ocean is the] most beautiful nation on Earth, a nation whose laws are harsh yet simple, a nation that never cheats, which is immense and without borders, where life is lived in the present. In this limitless nation, this nation of wind, light, and peace, there is no other ruler besides the sea.”

-Moitessier, A great French single-hander

At sea on your own boat, you are truly the king of your own castle. Here, you can do whatever you like, whenever you like, as long as you accept the consequences of your actions. There is no person but yourself to blame for any mistakes. At sea, you are truly in charge of your own destiny. 

You Don’t Know What You Don’t Know

Before I decided to attempt a solo circumnavigation on my own boat, I read every book, magazine article, and blog post I could find to develop a deep understanding of what I was about to get myself into. But in all of those inspirational stories and Ted talk videos, I didn’t find one piece of information that truly prepared me for the reality of what it takes to sail around the world. 

All these years later, I wrote this so that you can read the guide that I wanted to read but couldn’t find. I wrote the guide that really dives into the deep end of the pool and uncovers the reality of sailing around the world – warts and all. 

So, here it is. 

Things to Know Before You Sail Around the World

Before you commit to the greatest challenge of your life, you need to do some hard thinking to decide if this is the right lifestyle for you. In order to do that, you need to understand what sailing around the world is really like. 

Goal: Take a 3 Year Westabout Cruise Around the World

There are many different ways to sail around the world. Some people take ten or fifteen years to complete the voyage, sailing only a few thousand miles per year and sometimes staying in one country for many months or even years to work and rest. On the other end of the spectrum, professional racing sailors have blasted their way around the world in under 50 days on 100-foot multihulls capable of maintaining speeds in excess of 30 knots for days at a time. 

For our purposes, we will develop a plan around the most achievable circumnavigation for the average sailor – a three-year westabout world cruise through the tradewinds via the Panama Canal and South Africa.

This is the easiest way to sail around the world (if such a word can be used to describe a circumnavigation) and the plan that most often leads to success. Every year, perhaps two hundred small vessels complete this type of circumnavigation, and with a lot of hard work and some luck, you could be one of them. 

The typical distance sailed for this route is 30,000 nautical miles total. At an average daily distance of 100 nm on passage, this means a total of 300 days at sea or 100 days per year for three years. The other 265 days each year will mostly be spent at anchor or sometimes in a marina when you have the extra cash to travel inland or need to haul out the boat for hurricane season. 

Sailing around the world is a full-time job. Many non-sailors think that being out of sight of land for weeks on end must be incredibly boring, but in reality, chances are you will be incredibly busy more often than not. So, what would you be doing at sea, exactly?


First, you will spend a lot of time simply keeping the boat sailing in the right direction – reefing and unreefing sails, adjusting the wind vane or autopilot, trimming the sheets, checking the course, and that kind of thing. You will spend a lot of time plotting your position and navigating, checking your progress, and planning the route. Much time will be spent analyzing the weather, watching for squalls, storms, or calms, and obtaining and examining weather forecasts in depth. You will need to keep a constant eye out for ships and other hazards to navigation. Of course, you will have to dedicate time to keeping your crew healthy, well-fed, and in good spirits. 

Boat Maintenance

At sea, mechanical and electrical systems have a way of breaking down and chances are there will always be something that needs to be repaired. The engine will need constant maintenance and you will need to keep the ship as clean and organized as possible. A messy room on land is simply distasteful, but at sea it can be a danger. Unsecured items could fly across the cabin and break or cause injury to an unsuspecting crew member.

A famous American sailor was once knocked unconscious when the rather hefty volume of Heavy Weather Sailing Tactics – How to Stay Safe in Rough Weather flew across the cabin and hit him in the head. The author never mentioned in the text that his own book could be one of the hazards of sailing in heavy weather. 

Preparing for Landfall  

As you approach land, it will be time to ready the crew and vessel for landfall. You will need to be prepared to deal with a new language and different customs in each new country that you visit. Close to land, you will need to be especially careful to avoid rocks, reefs, floating hazards, and other vessels. Most likely, you will have very little free time in between ports of call to dedicate to your remote work.

Dealing with Risks and Uncertainty

At sea, there is a very fine line between safety and danger. Even the most cautious captain is almost guaranteed to have to deal with some kind of emergency at some point. A medical problem that could be quickly dealt with ashore can easily turn into a life threatening situation a thousand miles from the nearest hospital. One broken shroud can cause the mast to break, turning a routine passage into a survival situation.

There is a good chance that at some point you will have to deal with a severe storm, and you will need to be prepared to make it safely through both calm and storm at times on your voyage.

Lack of wind may sound like nothing compared to a bad storm, but many highly experienced sailors dread the doldrums more than any hurricane. Combined with a broken engine or low fuel capacity, a calm can quickly turn even the most hardened sailor into a mad case quicker than you might think. I once spent three long weeks becalmed off the Galapagos Islands, slowly running out of food and water on a non motorized 27 foot boat, and they were some of the worst weeks of my life. I wouldn’t wish that same experience on my worst enemy. 

In order to sail around the world, you need to be able to handle uncertainty and risk in a calm and collected manner. Think about times when you faced adversity, and how you managed. If you are able to deal with difficult circumstances without too much anxiety or panic, those attributes will help you deal with unexpected challenges on your expedition around the world. 

When you are cruising coastally, your time will likely be split between your remote work, keeping your vessel in good working order, and traveling around the countries that you visit. To keep costs down, you will probably want to spend most of your nights at anchor and do as much traveling as possible by sailing along the coastlines on your own vessel.

Depending on your route, you may need to spend between three and five months of the year with the vessel secured in a safe port to wait out the hurricane season. This is a good time to do as much of your remote work as possible and to fly home to visit with friends and family (If that’s in your budget.). 

Working at Sea

You will want to put a lot of thought into what kind of work you will be able to do to support yourself along the way. World cruisers are an innovative bunch, and they have found many different means of employment as they sail around the world. 

Remote Work

One option that is more feasible now than ever before is working online. The easiest way for most cruisers to do this is by purchasing a sim card and cellular data plan for each new country and trying your best to stay within range of cell service while cruising near shore. Of course, to make this work, you will need to work something out with your employer to be able to take time off while completing offshore passages, because satellite internet service is still priced far beyond the budgets of most working cruisers. 

Working Odd Jobs

In some countries (like Australia, New Zealand, Canada, and Ireland), it’s relatively easy for foreigners to get work permits, especially for farm work. This can be a good way to earn a few dollars while waiting for the appropriate season to continue your voyage. Other world voyagers work as doctors, dentists, mechanics, or electricians and offer their services to other cruisers along the way. Some do painting or woodwork on other boats or offer to fix sails or sew up cushions for a fee. 

For the past thirteen years, I have found work delivering boats from point A to B for owners who are unable to complete long passages themselves. This can be a nice way to make some extra cash, but there is little job security in this kind of work, so it’s best done alongside other means of employment. I’ve written for magazines and websites, worked as a landscaper, done charters, taught sailing lessons, offered my boat up on AirBnB, and done various other jobs along the way to bring home the bacon in between delivery gigs. 

If you are creative enough, there is always a way to keep enough money coming in to keep sailing west, but it’s a good idea to have an emergency fund set aside for hard times. 

Family Life At Sea

Another important factor to consider before setting sail for three years is your family. Will you be sailing with your spouse and children? What do they think about leaving everything behind to sail across the oceans on a small boat? Do you have elderly or sick relatives who need you close by? Are you ready to spend the vast majority of the next three years thousands of miles away from your loved ones? What kind of arrangements do you need to make in order to be away from your home for years at a time?

It’s important to carefully consider all of these factors before committing yourself to sailing around the world. 

Taking the First Steps to Sail Around the World

Once you have given the voyage some serious thought and made up your mind to sail around the world, it’s time to take the first initiatives to turn your dream into reality. In order to make this happen, there are two simple steps that will begin to lay the groundwork for your master plan. 

This guide was written in mind for someone with zero sailing experience and next to no money saved up. If you are already a relatively experienced sailor, or if you are lucky enough to have set aside a significant chunk of change that can be put towards your world voyage, then you can skip the first step or two and adjust this plan appropriately for your own personal situation. 

Let’s dive into the first 2 steps of how to start sailing around the world.

Step 1: Buy a Small Boat

Believe it or not, the very first step in sailing around the world is to buy a boat. But, not the boat that you will sail around the world on. That will come later, once you have saved up enough resources, accumulated the right knowledge, and gained the necessary real-life experience to know what boat you need to safely sail around the world. 

Your first boat will ideally be small and simple, like a basic daysailor or dinghy. In fact, the smaller the better. At this point, you don’t want to get caught up in all the complicated systems that you need to know how to use to navigate a larger vessel. 

For your first boat, you shouldn’t have to invest more than a few hundred dollars, a thousand dollars at most. Later, you can sell it and use the money to put towards a larger vessel or use the boat as your cruising dinghy. 

By choosing a small and simple boat for your first vessel, you can focus on the basic fundamentals of sailing, and worry about repairing a broken diesel engine or wiring in your chart plotter later. Besides, most of the tools that you need to navigate around the world are already in your pocket. (Yes, Garmin doesn’t want you to know this, but any regular smart phone can hold charts of the entire world on a boating app like Navionics or iSailor. As long as it has a built-in GPS, you are good to go just about anywhere. You don’t actually need a $10,000 navigation package to navigate offshore these days.)

The purpose of your first vessel will be to get you familiar with spending time on the water, to learn how to watch the weather, and build an understanding of how to get from A to B using the winds and the current. Your first vessel will turn you from a landlubber into a sailor.

Although it may be difficult to believe at the time, buying your first cheap little dinghy will be one of the most important steps in the greatest adventure of your life. Years later, after you have closed the circle of your circumnavigation, you will understand what I mean. 

Your first boat can be a used dinghy from craigslist, a plastic canoe from Walmart – almost any small, cheap vessel. It’s ideal to buy a boat with some kind of sailing rig, but even a simple rowboat or kayak will help you get out on the water. Rowboats, canoes, and kayaks can easily be converted into a basic daysailer, and the skills you develop building a simple sailing rig will come in use later on your circumnavigation when you need to repair sails or canvas. 

Sailing Your Own Boat

Once you have purchased and prepared your vessel (make sure to have all the necessary safety equipment, like a PDF, and some kind of waterproof communication device), it’s time to get out on the water. Most people who dream of sailing around the world live relatively close to a coastline, but even if you reside in the middle of Nebraska, chances are that there is some body of water relatively near your home that you can put to use to develop your boating skills. 

Download the Navionics app as well as a couple of marine weather apps on your smartphone and get familiar with the nautical charts for the area you will be sailing. This will be useful for your day sails, but also it will help you get familiar with some of the navigation and weather forecasting software that you will use later on your circumnavigation. I recommend using windy.com, passageweather.com, noaa.gov, and downloading GRIB files for analyzing the weather. 

Keep an eye on the weather report, and when the conditions are right (ideally light wind or near calm for your first sail) hit the water. 

Sailing your first small boat in local waters will help you develop the basic skills that will help you sail around the world. As you gain experience, your confidence will grow, and you will be more comfortable being out on the water even as the conditions freshen. You will learn when it’s safe to sail and when it’s best to wait for better conditions, and you will develop the patience that will be put to much use out on the ocean. 

Don’t Join a Local Yacht Club to Learn to Sail

Some boaters would recommend first crewing at a local yacht club before buying your own dinghy, but I believe that learning to sail first on your own vessel will better prepare you for your circumnavigation for a few reasons.

First, most beginner crew on the racing circuits are given one basic task on the boat, such as working the foredeck or trimming the sheets, rather than being given the opportunity to develop a wide range of skills in a short period of time. 

Secondly, greenhorn crew are usually taught to do as they are told and not question anything – quite the opposite of sailing your own boat around the world where you will need to make decisions yourself and be responsible for everything. By sailing your own boat first and crewing on other vessels later you will learn to think for yourself and understand basic sailing skills – rather than to obey authority, which is a useless skill in the middle of the ocean on your own boat. 

Now Decide If Sailing is Still Fun

After a few weeks on the water, you should have a really good idea of how much you enjoy sailing. On your circumnavigation, you will be sailing a much larger and sturdier vessel, but getting wet and tired (and sometimes scared) will still be very much part of the experience. If you end up hating sailing the small boat, it’s probably a better idea for you to buy an RV or book a Disney cruise instead of sailing around the world. If you have made it through a few knock downs and still can’t wait for your next daysail, then things are looking bright for your future at sea. 

Once you have gotten comfortable navigating your small boat, it’s time to go out for a longer sail. Pick a destination a little further away, and prepare yourself for an overnighter with your camping gear. Going camping with your small boat is an important part of your training for offshore sailing (especially if you plan to sail alone). This will help you get used to being self-sufficient and making do with the equipment that you have on hand. 

Eventually, you should work your way up to a week-long camping trip, either with the people you plan to sail with on your circumnavigation or alone. This voyage will be as much a psychological test as a physical one. After all, in the middle of the ocean, you won’t have other people to turn to for help other than your crew. 

This week-long voyage is your ultimate test. If you can live self-sufficiently for a week from a small dinghy and return home with a smile on your face, chances are you have what it takes to sail around the world. 

Step 2: Set Up a Circumnavigation Savings Account

Let’s face it, sailing around the world isn’t cheap. For a classic three-year circumnavigation, most couples end up spending around $250,000 to $500,000 including the cost of the boat. Some spend millions. While it’s very much possible for a frugal sailor to circumnavigate on a much smaller budget, any voyage around the world will take a significant dent in your savings. For the average person, saving up enough money to depart in the first place is the hardest part of sailing around the world. This is the hurdle that eliminates 95% of would-be circumnavigators.

Let’s assume that you are like the vast majority of Americans right now, and don’t even have enough money to pay for an unexpected medical emergency. How the hell are you supposed to pay for a world voyage? 

Sailing on a Budget

The good news is that there have been many examples of working class people who found ways to sail around the world with little to no money to start with. There are ways to find work along the way and support yourself as you cruise, and with the recent widespread adoption of remote work all over the world, it’s now more feasible to do this than ever before. 

Once you depart, you will have a portable home that can be transported almost anywhere in the world by harnessing the power of the wind – which is still free. By living at anchor rather than in expensive marinas, you can cut your housing costs down to near zero. You can stock up on large quantities of foods where they can be obtained for cheap, and carry supplies to survive for months, if necessary. In fact, cruising on a small sailboat is perhaps the finest low budget off-grid lifestyle today.

But even the most frugal sailor still needs money to clear into countries, pay for unexpected expenses, and to eat. You will have to maintain your vessel, and you first need to buy and outfit the boat in the first place. You can make this possible by setting up a savings account for your world cruise. 

Set up a savings account that is only to be used for your round the world voyage. With this account, money only goes in – until you have saved up enough to buy your cruising boat. 

Even if you open it with $20, that’s a start. Then you need to determine how much money you will set aside from every paycheck to go towards your dream. Before buying my most recent vessel, I decided that 50% of everything I earned would go into my voyage savings account. You will need to determine how much you can set aside based on your earnings and your living costs, but whatever you decide – stick with it. It’s all too easy to slip and spend your money on a nice dinner or a weekend vacation, but in order to pull off your dream of sailing around the world, you can’t afford to fall for these kinds of temptations.

You will probably need to find creative ways to cut your living costs down, like buying cheap groceries or moving back in with your sister. You may need to pick up an extra part-time job or side hustle.  It’s not pleasant at the time, but that’s what it takes to make this thing happen. You’ll thank yourself later while anchored off Tahiti. 

Slowly but surely, your savings will grow, and you’ll be that much closer to casting off your dock lines. You might not realize it yet, but you are already on your way around the world. 

Final Thoughts

Stay tuned to our next guide to learn more about how to sail around the world and work remotely.

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