How can I afford to go sailing, to stay out there?
Well, that is a very good question.
So if you are interested in how you can afford to sail once you have cast off the ropes that bind you to land-based living read on.
These are just my own observations on having to find a way to do just that, with a family to feed and kids to put through education without any land-based funds to fall back on.
So this Episode is not really geared towards the live-aboard in one place or area sailer, but for those who want to actively cruise away to “other “countries.
Visit remote corners and stay until their visa runs out.
And not an easy one to answer as it depends on so much.
But one of the biggest “depends on” is your comfort level in facing down the unknown.
And
What it is you do, or at least what skills you have that you can take with you.
You will learn new ones out there. But any skill takes time to develop, even more so if you need others to pay for them.
Not everyone is an artistic genius or a budding wordsmith, nor does everyone make or want to earn living off their computer/internet.
Trades are very good example of this, Artistic and Shakespearean individuals aside.
So this is not intended to be a Downer but hopefully will prepare you for a little of the realities out there and be prepared to make the most of every opportunity that comes by.
BE POSITIVE
Food and enough money to look after the immediate needs of your boat. Also things like visa and permit costs, fuel, entertainment, repairs, insurance, fun off the boat, flights back home?
End of cruising life Planning??
Which of this stuff can you reduce or cross off? Obviously, food and bureaucratic stuff plus immediate boat needs have to stay, fuel??
The rest is up to you and your comfort levels.
A good example is an air-con on board. Incredibly nice to have but very expensive in term of maintenance and running costs. In my mind, better off to put money into a few more fans and some wind scoops, Or in our case some decent shade cloth. Same with toilets, simple marine or computing or high tech “domestic” style?
The longer you cruise the less important many things seem.
And the less stuff you have, the less you have to earn for breakages and running costs. Because “everything” breaks and waiting around for warranty replacements adds up in costs, internet, taxis, marina fees AND shore side temptations.
So let’s start off with where we have found what other people have their money come from.
This is once you cast-off and a regular or commutable job not possible.
Broad brush strokes here
1/ Took an early retirement from the military or armed forces. We met many cruisers who had taken this option.
2/ On a pension, the silver seas crowd, a floating caravan of RVs. Often find that the pension goes further on a boat.
3/ On Sabbatical – a year or so off to sail
4/ Independent land income – all sorts here, basically either invented something, created something, or have a house/business ashore or have a large stash of money somewhere.
5/ Worked really hard, saved and now enjoying life afloat, also mixed with 2 and 4
6/ Sail a bit then leave the boat on the hard, fly out to work for a while for savings. All sort here trades, nurses, teachers,
7/ The “she’ll be right” will work things out. Also, al sort here, although tend to be younger, I wonder why 😉
Numbers 1 – 5 are people who have got their shit together.
Number 6 at least they are on their boat out there.
Number 7 is for those who dream and can’t wait for 1 – 5
Cast off and Off we go!
I think we have enough savings for a year or so but I’m sure we’ll work something out after that.
So soon enough your balance is getting low and you’re starting to think “DANG” gotta do something soon.
If you are in a country that allows you to work then maybe not so hard, all sorts of options open up, what you did before or something new.
But most places you visit will not be like this, language problems, not knowing anyone, transient nature of being a cruiser and the big one – illegal working.
So what to do?
Well if you have a skill you can sell to other more well-off cruisers, refrigeration, rigging, sail or mechanical, maybe a bit, but most cruisers are pretty good at this stuff anyway.
Finding boats in need, to fund your cruising lifestyle is rare. Totally different mindset once you hit a Marina. In a marina, the mindset changes and wallets will open up.
So
Marinas cost money. —> so you need to work to pay for the marina —> to pay for the work possibility..
And the locals whose food you are taking off their table may not appreciate you, so expect a visit from immigration, or worse!
I know a lot of unpleasant stories of being caught doing work where you shouldn’t.

The good news is there are opportunities
Internet-based incomes are possible,
Youtube (Paetron) for the very, very select few,
Writing and photography for those with the right skills and contacts.
Online sales of things that you can make e.g. jewellery
Useable skills, Electrical, refrigeration mechanical and rigging are obvious, not a regular income unless you hang out in a Marina or crowded anchorage
Opening up your boat to AirBnB or the like.
Paying crew, (not charter work). I say not charter work, or at least not illegal, that’s a fast way to lose your boat or minimum pay a hefty “fine.
Finding a niche somewhere, thinking outside the box, tapping the unique advantage of your location and being on a boat, looking at the local economy and seeing how you can fit in and help. A win-win situation.

Discover the internet (again)!!
Ahh the answer to all our problems,.
Something you can make then sells online. Jewellery, writing, photo/video are possible, but you need this stuff sorted before you go, and not everywhere has good reliable internet or postage. And it’s really competitive.
Being cruisers without a satellite comms budget we have spent many hours of frustration sorting out how and where to find an internet connection AND keep the thing connected as you cruise to different destinations. Signal boosters, extra cables. Always within sight of a cell phone tower 🙂
And this was just for the Kids education where a few days or a week or so delay wasn’t too bad. Trying to run a business like this sounds like a stress factory. Unless you have someone onshore who can look after the daily chores that every business has.
The biggest limit is how much you think you need, it might not be as much as you think.
Take food:
Many places are cash poor but have food to give.
Remote places have things that need fixing, electronics, generators, welding jobs.
Giving your time to help freely opens up the community.
As a cruiser, you really do have Time.
Things that can help:
Taking cheap reading glasses, this really helps
Gifts of pencils and paper., Crayons, Chalk
Fish hooks
Cruising with kids, children just about always open the doors to a community, but obviously not a long-term solution,
but man it’s amazing how many cultures will “open”’ up once they see kids onboard.
For us, it was perhaps more a #7 An “she’ll be right” or “something will turn up” or “deal with it at the time” attitude.
Possibly not the most responsible way of dealing with the issue of cruising and earning an income, especially with three boys needing food and an education.
For us we had sold everything up and bought Tiare, we had what we thought were a 2 -3 years funds to see us through before the “oh shit” moment arrived.
Our oldest son was determined to go to University, Early. So that took out the savings.
When looking for a boat I knew we were going to run out of money and we bought Tiare with this in mind as she was already set up for the budget end chartering, and I knew that this was what we were going to have to do eventually, plus if I could build a business around this it would make Tiare potentially more attractive when it was time to sell her.
But that was for a longer-term plan.
More immediately was putting food on the table and making sure our boys got a good education.
So another plan was called for, after looking at all the options (#6) decide the only thing to do was fall back on my trade as an electrician. Which I had not done for 20+ years.
Managed to find work a few jobs in a marina we were staying at, but again, tied to the dock and illegal work was always a niggle in the back of my mind.
So I flew out for a few months, which was hard. But came back with enough to cruise again. Did this for a few years, FIFO or fly in fly out work, this was good money and allowed us to put the boys through school (GSCE online) and help our oldest with the university. However, it was not a long-term solution.
Not long term because the good pay, short contracts, tends to be in the more “difficult or hostile” locations and being away from the family was difficult.
So what have we done after the money has gone?
Ashore – Worked off Tiare in a marina
Ashore – Fly In Fly Out
Ashore – Phoned up various wineries to see if they needed a cooper. One in Thailand did!
Internet- Build up the Robship brand online
Onboard – Opened up Tiare to Airbnb
Onboard – Slowly building up an inexpensive charter model
Ashore – Yacht repairs and maintenance at local marinas
One other … but that’s launching later this year <— excited about this
And very slowly growing this channel, don’t expect to make a cent but is a very good way to create a log of what has been happening and a way to develop skills.
No such thing as easy money.
Everything takes time

But what about you?
Where do you put yourself
Cast off with an open mind, a smile and sail off into the unknown. Just being out there opens new possibilities, choices you couldn’t have imagined previously.
Like all leaps, it’s not easy and nearly always scary, but that is life, you arrive into an unknown future and a path that is uncharted. A future that only makes sense as you begin to understand the choices made.
BE POSITIVE AND STAY FOCUSED ON WHY YOU WENT SAILING IN THE FIRST PLACE