Making Money Living Your Dream: Earning While Cruising

Because money doesn't grow on trees...not even in the Caribbean.

What if you could make money while living your dream?  If that's not the ultimate "having your cake and eating it too" I don't know what is.  We hear from so many readers - fellow dreamers and gypsies - who are itching to take the great leap into living their dreams (be it on a boat or otherwise) and they want to know how to make it happen without winding up completely broke and penniless in the end.

And therein lies the conundrum:  How to break free but not break the bank?

We were honored to speak briefly at Strictly Sail on this very subject during a seminar given by our friends Paul and Sheryl Shard of Distant Shores and it inspired me to write more in-depth on this subject.  While we do not have the answers or the magic formula, we have met quite a few people in our travels who are making their dreams work for them so I thought I would share what we have learned with you.

To give you a little background, Scott and I were very lucky to be able to sustain our dream of living on a boat and cruising the Caribbean while still bringing in a regular income.  Scott, who is nothing if not determined, set his eyes on getting his captain's license a couple years ago and with a lot of hard work and even more luck (and a nice dose of serendipity thrown in for good measure), he landed a job as a relief captain on a 100 foot schooner for Island Windjammers, an American company based in Grenada (it's not common to go right to a captain's position after getting your license - but IWJ took a risk on Scott and it paid off).  He worked one month every three months and because living on a boat is significantly cheaper than living on land, we made more than enough money to live on and then some.  It was great.

Now, however, things have changed for us (what with operation "family supersize" and all) and we will have not one, but three young children with us.  One child is easy to handle as a single parent (or at least do-able) - but three?  Game changer.  The prospect of being alone on the boat for a month at a time as a single mom of three girls is not realistic (or safe) so we are currently exploring other avenues.  We will keep you posted on this front.

So what are some of the ways people make money while living their dreams?  Let's take a look...Keep in mind, the pros and cons I list are off the top of my head - if you have experience with making money any of these methods and have something to detract or add, we would love to hear your thoughts in our comments.  I have included links to cruisers (most of whom are personal friends) who are actually making money these methods as well, and I encourage you to check out their sites to learn more.  It is also important to note that many of these ways are not providing an actual "living" but merely "supplementing" the cruising kitty and adding a few bucks here and there.  But a drop in the bucket is better than nothing right?  Read on...

1. Writing:  I am listing this one first as it seems to be the #1 way people think they will earn money while cruising.  While you certainly can make money writing articles for sailing magazines and such, you should also be realistic that you are probably not going to make a lot of money.  The writing world is very, very competitive and cruising is a very niche market with only so many publications so there isn't a ton of opportunity.  There are very few people who can actually sustain the cruising lifestyle with their writing, though it can be a way to supplement and make a few bucks here and there if you have talent.  Fatty Goodlander, one of the most successful and prolific cruising writers out there today, writes four hours every single day.  He's written a bunch of books and thousands of articles and makes no bones about the fact that they do not make a lot of money and live on the cheap (very happily, I might add).
• Pros:  You can do it anywhere, inspiration is everywhere, almost zero startup cost/investment.
• Cons:  Very competitive, pay out is small, time commitment is significant, reliable internet is necessary from time to time.
• Example:  The infamous Fatty Goodlander


2. Running/working for a business from your boat:  We have met a few people who successfully run businesses back home from their boats.  These folks work remotely by attending weekly conference calls via Skype and working online during the week, possibly flying back home with some regularity to show face.  Obviously, the nature of the business must be so that you are not needed face to face on a regular basis, but this is a viable option if your business or company allows, and if you have a great support team on the home front.  IT, web design, graphic design and other internet-based jobs lend themselves well to this sort of thing.  This does require adequate internet which is not something you always have while traveling abroad to remote places so this can be challenging.  If you go this route, you will most certainly need to invest in some sort of high-powered wifi booster to make sure you can connect when you need to and you will probably have to be based (or not far from) places with very strong internet signal (which will limit where you can cruise).
• Pros:  You can do what you know, you have infrastructure on the home front, good money.
• Cons:  You will rely on strong internet connection (many wifi hotspots in anchorages around the Caribbean are not strong enough to support Skype calls, FYI and are often painfully slow), and as such, you might be a slave to places with good wifi or have to rely on going ashore to connect.  Running a business remotely is not easy and requires significant organization and a reliable team on the "home front."
• Example:  Our friends Tasha and Ryan of Turf to Surf


3. Chartering your own boat:  This is when you take passengers on your boat for adventures/vacations.  This is a tremendous amount of work and requires that you invest in a boat adequate enough to hold both your crew and your passengers in private rooms or bunks.  It also requires that you hold a captain's license and anyone else who works on the boat alongside you must also carry their STCW certificate - both of which require a significant investment.
• Pros:  Freedom of making your itinerary (you can cruise where you want), you are your own boss, you get to share your lifestyle with others which can be refreshing.
• Cons:  Sharing your home with strangers, very competitive, slave to a schedule, incredibly hard work when passengers are aboard (you cook three meals a day, clean, and look after them), guests can be great or awful and you have to live on top of them for days or possibly weeks at a time.  I repeat:  this is very hard work - long days, long hours. You are in charge of paying for maintenance and repairs, insurance costs are high. 
• Example: John and Amanda Neal of Mahina Expeditions


4. Charter running another boat:  This is similar to above, but you work for an owner or charter company running someone else's boat.  People who work on mega-yachts are the most common workers in this category as are captains who work for charter companies.
• Pros:  Good pay, you're still living on a boat in the islands, you get to share what you love with others, someone else is usually in charge of the booking, someone else is usually paying the maintenance/repair bills.
• Cons:  Very grueling work schedule, very competitive, you are at the mercy of your boss/charter company, you do not cruise for you, but for others, very hard work (again, cooking, cleaning, boat maintenance), you are in the service industry and might have to deal with unruly guests.  You are married to the boat you work on so personal free time is compromised.  This type of work is probably not a possibility for cruising families.  You also need the requisite licenses to do this (captain's license, STCW, etc.) which, again, are a significant financial investment.
• Example:  Our friends Mike and Rebecca of Zero to Cruising


5. Delivery Captain:  We've met a bunch of cruisers who supplement the cruising kitty by delivering other people's boats from point A to point B for them.  This can be a very lucrative endeavor but involves a lot of offshore miles and many days at sea at a time.  It is far from glamorous but a good way to stockpile some cash relatively quickly.
• Pros:  You can pick and chose what jobs you take, you get to sail other people's boats and someone else is footing the bill.
• Cons:  Very competitive and not easy to get your name out there.  This is also risky business as you are sailing other people's boats and are therefore at the mercy of their maintenance and gear or lack there of (we once met a delivery captain who was supposed to take a boat from Florida to the VI's but refused based on the state of the vessel).  You often must adhere to strict schedules and deadlines which means sometimes sailing in less than ideal (or downright awful) conditions.  Significant time away from family.  You will often need to bring along at least one other paid crew member, which will cut into your earnings a bit.  
• Example: Our friend Christopher (and family) of Wandering Dolphin


6. Run an industry related business:  Cruisers are nothing if not innovative and we have met and heard of several that have found a niche or need and developed great products to sell to fellow cruisers.
• Pros:  Good money, you are your own boss, working with like-minded folks in an world you know and love (boating/cruising), you can be a traveling salesmen and your audience is all around you.
• Cons:  You are still running a business and this takes a lot of time and commitment.  You will probably need a person or team of people on land to help distribute and/or run customer service for you.  Depending on your business you must make a significant investment upfront to get it up and running.  You will still need to be "connected" a lot to fill orders, answer questions and ensure customers are happy.
• Example: Rich from s/v Third Day, owner of Cruise RO Water and Power, Paul and Sheryl Shard of Distant Shores,  Mark and Liesbet, creators and distributors of The Wirie wifi booster


7. Relief Captain:  working part time for a charter company or cruise company as the "relief" for the main captain (Scott's rotation was one month on, three off).  Again, this requires the captain's license and other relevant certificates and finding these kind of jobs is akin to finding a needle in a haystack.
• Pros:  Less rigorous work schedule, usually there is a little flexibility involved, decent pay.
• Cons:  Difficult to find this work, time away from family, pauses in your own cruising for weeks or months on end, cruising on a deadline to ensure you get to your place of work.
• Example:  Scott of Windtraveler (yeah, that's us!)


8. Living off investments on land:  We have met many cruisers (and travelers) who either rent out their paid off land-based home and live off that income, or have several "income properties" that bring in a monthly sum and they live off the net income from those.  There are obvious costs (and risks) involved in being a hands-off landlord, but it can be done.  For the record, this is the next step for us and the avenue we are currently pursuing.
• Pros: Can make some decent money and when you have the right formula (properties, partners, tenants), this can work very well for the vagabond lifestyle.
• Cons:  Lots of investment up front, must have a reliable partner or management company to work with, at the mercy of tenants, risky business if tenants are unreliable or unruly, stressful being a landlord, requires semi-frequent returns to the home-front to check up and maintain properties.


9. Blogging:  While there are a lot of people on the internet who make a living with their blogs, I have yet to meet a cruiser who makes a living this way.  Like writing, blogging is very competitive and making significant money requires much more traffic than many sailing blogs will ever get.  It is, however, a nice way to supplement the cruising kitty and bring in a few bucks  each month with things like affiliate links (ex. most cruising bloggers are Amazon Associates) and banner ads - but again, you must have traffic to get people to click on those links.  You can also save some good coin with sponsorships as we have. 
• Pros:  If you enjoy blogging, this is very fun and rewarding.  You get to chronicle your adventure and help others embark on theirs, you make great relationships with other bloggers.  Check out my post Tips for Cruising Bloggers to learn more.
• Cons:  Very competitive, financial gain nominal unless you have a LOT of traffic, requires many hours of work and time in front of the computer to do it well and be successful (I spend between 2-4 hours on this blog a day.) Takes a very long time (months or years) to ramp up and get a big audience, also relies on decent internet connection regularly.
• Example:  Friends Behan of s/v Totem who blogs for bucks on Sailfeed, and Carolyn of The Boat Galley


10. Online Trading:  Playing the stock market and making trades using an online trading site.  Pat Schulte of Bumfuzzle wrote a very detailed book, Live on the Margin, on how to do just this, you can check out my review here.
• Pros:  Easy to set up and get started.  Possible high reward.
• Cons:  Need some money to start up, signifiant risk involved, requires reliable internet regularly to check positions and manage portfolio.
• Example:  Pat and Ali Schulte of Bumfuzzle


11. Freelancing:  Using your skills in photography, web design, social media, marketing,  IT or something similar and freelancing as you go.
• Pros:  You are in control of your income and the hours you work.  Can make decent money if your skill is in demand.
• Cons:  Competitive, hard to find work, typically a feast or famine sort of gig, requires a lot of self promotion and possibly lots of time on the computer, oftentimes require reliable internet connection.
• Example:  Taru Tuomi, amazing freelance photographer of World Tour Stories,  Mercedes Villa Lopez, freelance graphic designer cruising the South Pacific


12. Cruising part time, working part time:  Not all cruisers are full time and sometimes going home during hurricane season offers a nice balance and can really keep you from getting "burned out" from the full-on live-aboard lifestyle.  Cruising part time and working part time offers a nice work/life balance if you can find a job that will allow for this kind of schedule.
• Pros:  Nice work life balance.  Very sustainable if you find the right situation.
• Cons:  You have to constantly take your boat in and out of commission, you must pay to store your boat somewhere as well as pay for some sort of "home base" on land, not easy to find jobs that are conducive to this type of schedule but they do exist (seasonal jobs probably offer the best bet).
• Example:  Our former buddy boat George from Earthling Sailor


13. Finding work along the way:  This sounds like a great way to go - just stopping and working along the way - but there are many complications that make this tricky, difficult, and potentially illegal.  Finding work in another country is not easy (especially if the countries you are traveling to are "developing" as most of the ones we visit are) and often requires very expensive and hard to obtain work permits.  If you decide to skirt the permits and work "under the table", you risk legal issues.  
• Pros: You stop and really get to know a place, you make money as you need and cruise freely the rest of the time.
• Cons:  Very difficult to find, requires you to stop cruising for significant lengths of time, possibly need to move off the boat and onto a land base for a while.
• Example:  Our good friends Eben and Genevieve of Necesse who are currently working in the Dominican Republic


14. Selling a trade: Some cruisers work from their boats as shipwrights, sailmakers, canvas workers, massage therapists, hairstylists and more.  This is a decent and relatively easy way to supplement, but cruisers are a famously thrifty bunch and more often than not you might find yourself trading goods instead of getting paid actual cash for your services.  Other services that are in high demand with cruisers:  marine electrician, diesel mechanic, marine refrigeration expert, and specialty guides (kitesurfing instructor, dive instructor, yoga instructor... etc).
• Pros: You can do this from any anchorage anywhere you are, you will meet lots of other cruisers, your "clients" are literally all around you.
• Cons:  Working "under the table" for cash in a foreign country might pose legal issues, cruisers - as a rule - are a pretty cheap group and might not be willing to pay for your services, must creatively advertise and market yourself. 


15. Selling a craft:  there are so many cruisers with incredible artistic talents for handi-crafts. Nowadays, with online storefronts like Cafepress and Etsy it's pretty easy to set up your own shop where you can sell your goods and art.  We have met cruisers who sell their art, tee-shirts, jewelry, music, knitting and more.  The money is probably not so much that you can make a living, but it might be a nice supplement. 
• Pros:  You can create art that you love, arts and crafts are a great way to pass time on a boat, can possibly sell your crafts to fellow cruisers while underway but you can also reach a wider audience with online storefronts like those mentioned above.
• Cons:  You must carry supplies enough to meet the demand, shipping items from far-flung places might get tricky, you might need to have a partner on the home front to help manage orders if you can't manage it from afar, requires reliable internet, must have decent marketing skills to get the word out there as the craft market is pretty saturated.
• Example: Former cruising buddy and nature artist Lara of Forest and Fin and friend and jewelry designer Melody of Maggie&Millie, Chris DiCroche - singer and songwriter of MondoVacilando.

The bottom line:  there are ways to make it happen, but it will take sacrifice, creativity and some good old fashioned perseverance.

Other informative posts by fellow bloggers on this same subject:

Earning Money While Cruising:  Lessons from the Pros (we contributed to this one)
Making Money While Cruising from our friends Paul and Sheryl at Distant Shores
Wireless Ideology a website dedicated to interviews with "Digital Nomads" (see our interview here)


Do you currently make money any of these ways?  I would love to hear your thoughts on the pros and cons and realities of it!  Do you make money a different way?   How have you made your dream work for you?  Please share in the comments with any tips, tricks and insights.