Sailing the Caribbean: Season 6 is Coming

Normally, people go cruising just to sail the Caribbean; these people also sail straight to the islands in the most direct way possible and thoroughly enjoy life. We went the really long way to get to the Caribbean, arriving after 4 years of cruising and two Atlantic crossings. It’s a good thing we did the other sailing first because we might have never left the Caribbean!

How to calculate wind shadows

Hiding in the lee of an island is a great way to protect yourself from punishing winds. The land blocks the sea from building waves that will rock your yacht as well as blocks the wind m, allowing you to anchor rather peacefully in some horrible conditions!

When you are looking at a new place to go cruising and need to find happy hiding holes that you can tuck into if the wind builds, how can you figure out how far away from land you will still be protected?

Navionics will tell you the elevation of various points on a landmass. Some are in feet, some are in meters, but the math all works out the same.
The equation is simple:

Elevation in Nautical Miles x 20 = Distance of wind shadow in nautical miles

For example: 564 feet (elevation) / 6076 feet (number of feet in 1 nautical mile) = 0.09nm tall

0.09nm x 20 = 1.85nm wind shadow

In other words, if you are within 1.8nm of that point of land, you will experience much less wind as you will be shielded from it.
Another example would be 168m right next to it:

168m x 39 (number of inches in a meter) = 6552 inches / 12 (number of inches in a foot) = 546 feet / 6076 (number of feet in a nautical mile) = 0.089 x 20 = 1.79nm wind shadow


To make it easy, just do these calculations:

If the elevation is in feet:

Elevation / 6076 x 20 = Windshadow

If the elevation is in meters:

Elevation x 39 / 12 / 6076 x 20 = Windshadow

How to make money while cruising

Cruising is a very cost effective way to live and travel the world. The wind is free, and it will carry you to distant shores well beyond the horizon; all you need is the patience to wait for it to get you there.

Expenses can be very low, just the food you need to eat and the parts you need to replace on your boat as they go wearing out. While you will have the time and knowhow to fix everything on your boat, you will still be faced by the hurdle that you will need to purchase the raw materials needed to carry out the repairs to keep your vessel sailing safely. So, how do you make money while sailing around?

There are a few options that we have seen over and over again by other cruisers. The first is to work on other peoples boats. Lots of people own boats but few people actually cruise on them and have the time to do the work themselves. This means that the majority of boats are owned by people who work a paying job and need maintenance/repairs carried out on their boat and simply don’t have the time to go do the work themselves.

Imagine if you work a full week and only have the weekend to go enjoy your boat. Do you want to get to your broken boat and begin working on it, or would you rather get to your boat and just go sailing? Everyone would rather the latter which is why people with money are willing to pay someone else to do the work for them. As a cruiser, you know how to fix everything on a boat and have loads of time on your hands. Working on someone else’s boat is a great way to make money without having to travel very far! You can also do work as you go, arriving in a new anchorage and taking on new jobs until you are finished with all the jobs available or tire of living in that anchorage and want to sail to somewhere new. Boat work pays very well and since you have very low expenses, this money will last you a very long time while you cruise!

Our monthly budget is still only $500 per month (even after 5 years of cruising). When I do a quick job and earn $100-$300, that represents 20%-60% of our entire months budget. With a couple of jobs a month, we can easily sustain ourselves while cruising and any additional money simply gives us more freedom until we need to find work again.

Another option, if you are tired of working on boats because it feels like that is all you ever do is to get a land based job in the town you are anchored near. We know a lot of people who get a quick low paying job like working at a grocery store or restaurant. This makes them some money to buy food and once they have enough, they set off again for a bit of freedom. When their funds wear down to the point that they need to find work again, they just find another grocery store or restaurant to work in.

While these jobs pay a respectable income while you are sailing around, they are not very glamourous jobs. Boat work is hard and dirty work, and minimum wage jobs are also hard work. What about the idea of filming yourself and becoming YouTube famous? Bust out a camera from time to time and record your self living an awesome life, upload it to the internet and have the money pour into your bank account! That’s the dream, right?

Well, it does help out but it isn’t a sure thing. It seems that everyone wants to become YouTube famous these days and they think that whatever they film is going to go viral and make them millions of dollars while they sleep at anchor. Making YouTube videos is a full time job that does not come without sacrifice.

While the cost of entry is pretty low, as the camera in the phone that you already have will seem like enough to make a video; there is a huge gap between those who are just filming for fun and those who are filming as a job.

When we started our YouTube Channel, we were filming with the GoPro Hero 5. This camera is a work horse and we used it constantly for about 2 years straight. It films really well in 1080p and the audio is Ok, but not great. The camera is water proof which is very important for a sailing channel, as the camera will get splashed!

This camera is a huge step up from a cell phone camera, but it pales in comparison to a β€œreal” camera; and as a result, the video quality just isn’t there.

After 2 years of making YouTube videos, we decided to upgrade our equipment and make this our primary job. We decided to stop making videos that were for β€œmemories” of our little voyage and instead work really hard to make really good videos. I took courses offered by YouTube that go very in depth into how to make a proper video, as well as studying videography courses and pretty much devoting myself to learning how to make every episode better than the last.

To improve or videos, we had to improve our equipment and our GoPro Hero 5 was replaced by an assortment of cameras that have their specific purposes. It’s like having a β€œscrewdriver” versus having a β€œPhillips Screwdriver and a Blade Screwdriver”. Specialized tools work better but only in their intended task.

Our camera armamentarium grew from a GoPro Hero 5 to a GoPro Hero 8, a Nikon D7500 with an assortment of lenses, and DJI Osmo.

The GoPro Hero 8 was simply an improved and updated version of the GoPro Hero 5 that we were very accustomed to. It had more features than the Hero 5, and it could film (with stabilization) in 4K.

4K footage was the biggest jump in quality that we could make and it set up apart from all the other channels that were β€œfilming for fun”. 4K files are massive and as a result we needed to upgrade the iPad we were using to edit on to get one with a bigger drive, as well as buy a boatload of SD cards to hold all this additional footage. Our SD cards would hold about 8 hours of 1080p footage or around 2 hours of 4K footage.

With prettier footage we were then more motivated to make a prettier video and push ourselves further with the cameras to get cooler and cooler shots. The DJI Osmo was very handy at getting shots where the gymbal was needed to steady the image, but nothing compares to the footage that could be captured by a proper camera.

The Nikon D7500 is our β€œpretty camera”. It can look at a turd and make the footage glow with beauty! This expensive camera also has interchangeable lenses and each lens costs a small fortune!

We have one automatic focus zoom lens that we use the majority of the time because it is very versatile, but we also have a collection of prime manual focus lenses that are absolutely stunning to look through. The footage we get with these lenses go beyond YouTube video and become art.

With all this added effort and work, our channel began to grow even faster and we started to make some actual money from it, enough that we decided to upgrade our primary camera, the GoPro Hero 8, to something a little better. Enter the Sony a6600.

The Sony a6600 is a glorified GoPro. It takes better video, has a zoom lens, and has pretty good stabilization in 4K, but it isn’t water proof.

Water proof is a massive requirement on a sailboat, especially if you want to get awesome storm footage. The camera will get splashed so you need to be able to afford to replace it when it gets splashed and dies a corroded death.

As you can see, the jump from β€œYouTube for fun” to β€œYouTube Career” is a pretty big one, one that we are just beginning to take as we improve our camera gear and upgrade our skills to create better and better videos.

If you are just picking up your phone and want to become YouTube famous, you will probably become frustrated when the big bucks don’t instantly arrive at your bank account.


It seems that the cost of making good YouTube videos pretty much outweighs the profits from making YouTube videos, so how does it all work out? How do people make a living from filming themselves as they sail around from one tropical paradise to another?

Well, YouTube isn’t the entire story. In fact, YouTube is only a tiny portion of the β€œpassive income” generated by videos. YouTube is a place to cast your voice upon the masses so that you can then drive earnings from other revenue streams.

Patreon is a common platform that creators use to help them on this path. At first, we felt odd about β€œasking people for money” through Patreon, but then we realized (after being told by one of our Patrons) that they were supporting us on Patreon so that we could continue to bring them videos. We all have a finite amount of time available to us, and the best way to ensure that we spent our time making videos about our adventures was to give us the financial independence to go make the videos. If we didn’t have that dependable income, we would probably have to stop making videos from time to time to go work a regular job.

Patreon was just the beginning of the income stream, as it was a very nice and dependable base that we could budget around. Our Patreon family grew and remains filled with people who want to see us grow and succeed instead of people who β€œwant stuff” from us. There are times when we are sailing across and ocean and have absolutely no internet access for almost an entire month. Our Patrons understand that we are out there gathering tons of amazing footage that they will get to see as soon as we can get it to them, and they wait patiently. There are other times when we have plenty of internet access and we all chat on a Patreon only group chat.

This base and security helps a lot to provide a dependable income as you begin to explore other revenue streams that could be much more profitable as you grow.

These other revenue streams are selling branded swag and gear to your viewers. It is very easy to design a T-shirt that will connect with your viewers. This can be something as simple as a running joke that you have on your channel or an awesome design that everyone would want to wear. There are companies that will sell, print, and ship your designs for you; handling everything for you (for a fee) and then sending you a portion of the sale price to you at the end of each month. This is awesome because you can also design the shirts that you wish to wear yourself rather than being forced into the social norms of wearing something that a professional designer came up with.

We sell our shirts through TeeSpring, but there are other companies out there that will provide a similar service.

Beyond selling stuff that you create, there is also the opportunity to sell stuff that other people create, and stuff that you use on a daily basis! This is the world of Affiliate Marketing.

Basically, you contact a company and ask to become an affiliate. They will give you a code or link and every time someone buys said product using your link or code, you will get a percentage as a β€œfinders fee”. The buyer pays nothing and the seller pays you, as your part comes out of their profit margin.

This comes in handy when it’s stuff that you use all the time, as people will see it in your videos and want to buy the item that you are using. Having the links in your description help make it even easier for this to all work out.

I have a few affiliate accounts, and they are all with companies that I feel make a good product. For years, I was simply free advertising for these companies as they are products that I have purchased and was then displaying over and over again in our videos. Now I found a way to earn a bit of income from this exposure.

Our current affiliate links are:

Mantus Anchors: https://www.mantusmarine.com/?affiliates=119

Overkill Solar: https://overkillsolar.com/?myboi=187478592

Battery Hookup: https://www.batteryhookup.com [Code: RIGGING5]

Amazon: https://www.amazon.com/shop/riggingdoctor

Aquos Electric Motors: https://www.aquospro.com?sca_ref=1008159.oxyRUafA2y

Amazon is an interesting one, as Amazon sells most everything these days. If someone clicks on your Amazon link and then buys anything, literally anything, you get a finders fee for the sale. You could put a link for your favorite anchor and someone clicks on that link and then decides not to buy the anchor but instead buy a nail clipper. You will get a finders fee for the nail clipper.

Naturally, as your channel grows, so does your audience and as a result you will generate more sales through your affiliate links. As your sales increase, you will begin to make more and more revenue from these sales until it eventually becomes your biggest revenue stream and affords you the ability to continue sailing indefinitely.

The trick to it all is to stick with your original budget as it will become very tempting to spend more as you make more. If you earn more money but continue to spend the same meager amount that you always did, you will find yourself with more financial independence and freedom to cruise without worrying about when you will need to pull into a port to find a job.


In summary. the way to earn money while cruising is:

Work a paying job, be it on someone else’s boat or on land.

Work a YouTube job, because it is a job when you really get down to it. It’s an awesome job that lets you live your best life; but it is a job and it takes a lot of work!

From your YouTube channel, you can expand to have a Patreon account which will help you with the costs of all the camera equipment needed to create your YouTube videos. You can then expand to sell merchandise for the channel and eventually create revenue streams from affiliate marketing.

How to afford to go cruising

You know the dream: Live your best life and get paid to do it!

It sounds fantastical and then you hear about someone who is doing just that. They are getting paid to sail around the world and enjoy every moment of their life. Why do they get to do it while you are stuck at the office?

The truth is, money while sailing is a simple equation:

Money Earned - Money Spent = Money to Cruise

This may seem over simplified, but it really is that simple. When you have your desk job, you have lots of money earned; for this example $100,000 earned.

So far, you have $100,000 but yet you can’t seem to afford to stop working and go cruising. This is because of the other part of the equation.

You need to factor in your house payment, car payment, insurance payment, groceries, fuel costs, entertainment costs; it all adds up and probably will get very close to your β€œMoney Earned” value which will leave you with $0 for β€œMoney to Cruise”.

Living in society is very expensive, and you have been conditioned to spend as much as you make because that is what keeps the economy going. If everyone worked hard and saved all their money, there would be no one buying all the junk that makes business thrive! As a result, there would be no business and therefore nowhere to work. To keep this giant hamster wheel spinning, everyone needs to spend as much as they make, and maybe even a little more spending this month so that they will have to work harder and throw interest charges into the mix!

It’s a huge scheme designed to keep you in your place and prevent you from actually living the life you want to live.

While cruising, you will make significantly less money, but you will also spend significantly less money.

I used to work full time as a dentist and I was making well over $120,000 per year. It was awesome and at the end of the year, I had barely any money left over because it was all spent before I made it. I have now been cruising for 5 years full time and actually have money saved up in the bank! How can I be saving money when I make less than $20,000 per year while I couldn’t save when I was making $120,000? Simple, the β€œMoney Spent” category go slashed.

When I went cruising, I got rid of my car which also got rid of my car payment and car insurance payment. I left the marina I lived in and now live at anchor which got rid of my slip payment. My entertainment costs went way down because instead of going out to an activity with friends, friends want to come over to the boat. When they come over, they all bring beer and other refreshments with them which means that I am the entertainment and therefore I don’t need to pay to be entertained anymore. I used to spend money on all sorts of things that I can’t even identify at this time because they were worthless money sucking unnecessary things that I do not miss at all.

Now, my expenses are food from the grocery store, meals at restaurants from time to time, and fuel for the generator. As parts on the boat breakdown, I fix them because I have the time. When they get past the point of fixing anymore, I replace them. Sometimes, it’s an expensive item like the generator that dies and costs a whopping $1,000, but the original one lasted and worked for 5 years. Most of those years were problem free, but over the past few years, the machine has become more and more problematic until it reaches the point where it no longer functions in a dependable manner and I decide to replace it.

Since I don’t spend money on other things, I have the cash on hand to buy such a replacement without sweating the expense.

The answer to β€œHow can you afford to go cruising?” should really be a question of β€œHow can you afford to stay at your job and not go cruising?”

By reducing your β€œMoney Spent” category, your β€œMoney Earned” category suddenly becomes so much more powerful and this gives you a lot of money to go cruising on.

The next question should be: How do you make money while cruising?

For that, you will have to check back tomorrow.