Where are all the new adventure posts?

Well, I’m catching up on finances, whittling away at that near-$5,000 boatyard bill that almost cleaned me out.

So I thought, since I’m not adding much else, now would be a good time to explain how I make money while cruising on a sailboat and how I make the most of what I have!  Since a lot of you think I’m on some kind of vacation

Turns out I had too much for one post, so here’s part one of two.

Making Money While Sailing

“Only he is successful in his business who makes that pursuit which affords him the highest pleasure sustain him.” – Thoreau

I’ve encountered three types of people on my voyages:

  • those who don’t really care about making money because they’re already very wealthy or retired and have good pensions
  • adventurers who are living off of savings while they’re cruising, then take a break to work hard and refill the bank
  • sailors who work while sailing

I fall between the second and third categories, though I’d have no complaints if I was in the first.  The first category is actually an extreme minority – the “they’re all wealthy” stereotype is far from truth.  That’s why you shouldn’t give up on this dream!

Years ago I started with this idea that the photographs from my voyages would sell and sustain me.

Ha, well it turns out that your Average Joe doesn’t go to the internet to buy photography made by your Slightly Above Average Joe.  I had a few appearing in small publications and still eventually make the random online sale, but it’s nothing I rely on.  So I went back to the drawing board.

I go about making money while sailing in a variety of ways now. Some of it is passive income and some is active work. Here’s the breakdown of what I do and what others do.


Casual Wednesday at the office. It follows Casual Tuesday and precedes Casual Thursday.

Writing & Freelancing

“Because in the end, you won’t remember the time you spent working in an office or mowing your lawn. Climb that goddamn mountain.” – Jack Kerouac

I currently write regularly for an online aviation magazine, a job that kind of fell in my lap through dumb luck and my experience as a flight instructor. This work also recently led to another job writing regularly for a large national flight school, effectively doubling my income from writing.  It’s a great way of making money wherever I can take my laptop.

But where can you find these jobs, and what if writing isn’t your thing?

There are a number of websites advertising for jobs like graphic design, editing, writing, data entry, transcription, etc.

I used to get my work from Elance, but Upwork.com has since aquired them (which has a lot of cheaper work). You’ll see a lot of jobs on there to “write 1,000 words for $5”. That’s kind of a joke, but you’ll have to swallow a couple of those to build up your portfolio and positive reviews. Once you have those good reviews, then you can get jobs that pay a respectable amount. Many of these jobs will lead to regular work with the employer, so you don’t have to keep searching every week.

I’m taking jobs on Upwork that pay $30-$50 for 500-1000 words, which comes out to about $25/hr if you want to break it down that way. I’ve also done things like writing questions for a Photoshop test and writing a guide to calculating a home’s square footage, both of which took me a day to do and paid just over $200 each.  Those single day jobs were two weeks worth of food!

There are other websites out there besides Upwork that you can check out, if you just do an internet search for “freelancing”.

Unfortunately these jobs will require electricity for your laptop and a fairly reliable internet connection.

On the bright side, renewable energy for sailboats is getting cheaper every year. And in addition to bars and restaurants, wireless access in anchorages is starting to proliferate (I’m writing this from my boat right now, on the hook in Mt. Hartman Bay, Grenada).


Many sailors blog about their travels. In fact, a lot of other people are making money while traveling by blogging about it. Many write every single thing they do every single day. I think that’s a little mundane – you don’t really want all of that, do you?

But how do you turn this into money? Affiliate marketing and advertising is the answer.

amazon associatesWhen I have a good experience with a product, I’ll either write a review about it or casually work it into another blog post. I’m an affiliate partner with Amazon, REI, and West Marine. If those companies offer these products, the link I post has a code that identifies me as the referrer. If a sale is made from that referral, on any item purchased (not just the product I referred), then I get between 5-10% commission on the sale.  Who wants to buy a $2,000 camera?

This is a tough one to see any real returns though. It requires active search engine keyword research, aggressive social media marketing, writing content that sells every week, and getting as much traffic to your website as you can before making any money.

Some call it “passive income” because it makes you money while you sleep, but it’s anything but passive. I spend a couple hours a day on this website between writing content, research, and social media marketing.

Many people have been very successful at it and some have been easily discouraged and quit. I made less than two dollars a month for the first two months doing this. Then eight dollars the third month, and seventeen dollars the fourth month. It was very discouraging at first but I kept at it, and I’m continuing to see my returns nearly double each month for the past eight months, now in the hundreds. I know this trend will eventually start to level off, but I’m excited to see how far I can take it! Try a bunch of different tactics, then when you figure out what works, focus on that.

Tyrell Bay, Carriacou


Ebooks have become a very popular way of making passive money. I’d venture to say that the ebook market is becoming oversaturated, based on the “ebook author” requests I see on freelance websites.

But if you have some information to offer the public, especially if there isn’t much out there about it, put it in an ebook and sell it on Amazon, Google Play, and iTunes.  It’s nice to get some beer money from it every month.

Just like everything else, this small income gets combined with others to add up to something bigger.

Investment Income

Own your house? Rent it out and live on your boat – but only if you don’t end up losing money on it.

This one requires a lot of money up-front, and it has risk, but it’s a good way to again get passive income if you can rent out your properties for more than mortgage, insurance, taxes, management, and maintenance costs. My rentals don’t earn me enough to make a living on, but I stay in the black and it’s more cash in the bank.

You can also get involved in financial trading if that’s your thing – another activity that you can do from your sailboat.

Work Like a Horse During Breaks

“There is no more fatal blunderer than he who consumes the greater part of his life getting his living.” – Thoreau


Saoirse sitting in her hole in the ground shortly before getting a lift onto the stands.

You may not believe it, but you’ll want to take a break from the sailing lifestyle every now and then. You might be forced to do it to go back home and take some work, to see family, or just for a change of scenery. Living on your boat and cruising for years without a break is an unrealistic expectation.

You’ll need a place to store the boat while you’re gone, preferably on land. I keep Saoirse at a boatyard in St. Kitts, the cheapest storage I’ve found so far.

During your break, get a temporary job and be disciplined about putting some of your earnings into your cruising fund. When you’re ready to return to the cruise you’ll have a good chunk of money to get you going.

Working on Location

Sewing a Winch CoverYou can get VERY creative with ways to make money in the harbor. One lady here in Grenada is making her money by looking after boats while the owners are away. Another gentleman, and this is something I wish I thought of, makes money by buying beer & wine wholesale and then delivering it to cruisers who call him on the radio with a beer order. Others scrub boat bottoms, sew & fix canvas work, do welding projects, and so on. The only limit is your imagination.

And local laws. Grenada requires a work permit. In Trinidad, local authorities are increasingly penalizing cruisers for taking jobs from locals. Just make sure you do it right wherever you are because you don’t want to find out what the penalties are.

And on that note, it is also possible to get employment on land wherever you are. If you just want to stay where you’re at for a while but need some money, apply for a work visa or work permit and see what you can find. You’ll be able to live on your boat so that takes care of rent!

Have Your Captain’s License?

This opens up another world of opportunity for making money on boats.  You can skipper boat deliveries, work for local sailing tours, charters, etc.  I don’t have this one yet but I think I may work on it soon.

The Money All Adds Up…

The above methods of making money are by no means all-inclusive. It’s just a small collection of what I do and what I see others do.  There are a number of other resources on the net, written by people in the same situation, but doing different things to make money.

By themselves, they’re nothing I can make a living on (yet).  But all combined, they cover my budget for all of my land-based expenses and all of my cruising expenses!  Part Two covers all of these.

You may already have a good, stable job that will allow you to work remotely – such as some IT, consulting, and web design jobs. And that’s great – you’re already ahead of most of us!

Just remember that cheesy saying – where there’s a will, there’s a way.  You can find a way to make it work if you put your mind to it.

“Going back to a simpler life based on living by sufficiency rather than excess is not a step backward.” – Yvon Chouinard

Do any of you sailors or other “digital nomads” have anything to add?  I’d love to hear about it below!

Now on to Part Two.

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