Earning Money while Cruising - Lessons from the Pros

"'I've always wanted to sail to the South Seas, but I can't afford it!'  What these men can't afford is not to go.  They are enmeshed in the cancerous discipline of security.  And in the worship of security we fling our lives beneath the wheels of routine and before we know it our lives are gone.” -Sterling Hayden from Wanderer

I've been dreaming and scheming about long-term cruising for a long while (perhaps too long). I think I've got a good handle on my own reasons for wanting to cruise, and maybe even a better handle on the metaphorical navigation hazards keeping us from cutting the lines. But no matter your individual situation, if you've spent anytime contemplating a long sailing voyage or the cruising lifestyle, then you understand that the costs of cruising can feel like a daunting, nagging issue. For that reason, there has already been much written about the topic. 

I’m hoping to approach the costs of cruising in this post from a slightly different angle. Instead of trying to make some generalizations about what it costs to cruise long-term on a sailboat (I’ve already done that here), I'm presenting some real world examples of cruisers currently making money while cruising with a variety of methods. If you’re independently wealthy or are starting out with a massive cruising kitty, then consider yourself fortunate that this blog post probably won’t have much relevance to your situation. On the other hand, if you’ve got the cruising itch and want some inspiration for making ends meet or replenishing your depleted kitty, read on!

Before I get to the real meat and potatoes, I’d like to thank the following folks who graciously took time to contribute when I asked for their input on the subject of working while cruising: Pat and Ali from Bumfuzzle, Brittany and Scott from Windtraveler, Paul and Sheryl Shard from Distant Shores, and Cap’n Fatty Goodlander.

If you know any of the above veteran cruisers or are familiar with their journeys, you know that each crew is using some form of work while cruising to help offset the costs. I asked them to answer the following two simple questions in hopes that their answers and experience will inspire and help others looking for solutions:

1) What skill/s do you need to be successful with this method of making money while cruising?

2) What is the biggest challenge with making money for cruising by using this method?

Here are their methods and responses:

Cap’n Fatty Goodlander: If it seems like Fatty has been writing and sailing forever, well, I think he has! In his own words, “We need money. But we like to sail. And we know that working can interfere with sailing if you’re not careful. So we’re very careful. This means a job-job is out. Frankly, I’ve never had a job that didn’t look good in my rear view mirror. Plus, we prefer to shun the shore…too many dirt-dwellers, shore-huggers and dock-queens for our tastes. So Instead we live by our wits. At sea. On landless atolls. Anchored off primitive islands. Far up uncharted rivers. In deserted safe harbors. …just beyond the jagged rim of civilization. …aboard the 52-foot schooner Elizabeth (built in 1924), the 22-foot double-ender (1932) Corina, the 36-foot Endurance ketch Carlotta (1974) and our current $3,000 hurricane-salvaged S&S-designed 38-foot sloop Wild Card. …we chase the horizon. Eternally.”

You’ve probably read some of Fatty’s books and columns in Cruising World magazine, so you know he’s a writing sailor. Or as he says, an “ink slinging sea gypsy”. Here’s how he answered my 2 questions about earning money while cruising by writing:

1) "Writing the truth is the bedrock skill of all successful writers. Truth always resonates."

2) "Staying focused on accomplishing my literary goals. There are only so many hours in a day. It is easy to get sidetracked. I get dozens of presumptuous requests to write for free each day---and I have yet to figure out a way to turn them down gracefully."

Take home message for becoming a writing sailor: Be truthful and stay focused. Short and sweet! If you need more writing advice from Fatty, check this: Writers Only!

Pat from Bumfuzzle: Pat and Ali recently swallowed the hook, but there’s much to learn from their circumnavigation and subsequent voyage along Mexico’s Pacific coast. How did they do it at such a young age? Trading stocks. Here’s how Pat answered my 2 questions about earning money while cruising by trading:

1) "Trading is all about managing risk, and if you are a sailor you manage risk every single time you take the boat out. Beating headlong into 35 knots in an effort to make it to that next anchorage, but then accepting that the risk to both yourself and the boat is unacceptable and tacking downwind to slide easily back into the anchorage you’ve just left is a perfect metaphor for trading. Any and all successful traders know how to take a loss. Trading a winning trade is easy—just like sailing in ten knots—but it’s how you handle the storms that really matters. I talk a lot about this in my book, Live on the Margin."

2) "The biggest challenge to making money in any endeavor while simultaneously cruising is managing your time. Nobody wants to go cruising only to find themselves working forty hours a week on top of all the work of managing a boat. For a trader out cruising the challenge becomes finding opportunities and making profitable trades inside of the small windows of time they have while in a port with good WiFi. I often go weeks or months without making a trade just because I’m off traveling and don’t want to dedicate the time necessary to trade. When I do find myself in port for an extended time I follow the markets more closely and watch for trading opportunities then. Also, I make it a rule not to carry open positions while I’m off the grid. This often means closing out positions earlier than I would have wanted to do and possibly giving up gains. But really, any job while cruising is going to require trade-offs."

Take home message for becoming a trading sailor: Learn to manage risk and time!

Brittany from Windtraveler: From Chicago to the Caribbean, and then throughout the Caribbean, Scott and Brittany have been openly sharing their experiences. While they started by living off a cruising kitty, they’ve kept it topped off by Scott working 1-1.5 months at a time in Caribbean as a ship’s captain and with Brittany finding an audience for her blog writing. Here’s how Brittany answered my 2 questions about earning money while cruising by both working as a captain and writing:

1) "Our situation was really due to a LOT of luck.  Scott started looking for jobs in Grenada, saw an ad for a deckhand position and when he inquired about it - the existing captain gave him some great advice, "You don't want to be deckhand, what you want is to be captain - get your captains license".  So when we came home the summer to have our baby, that is what Scott did.  Despite having zero commercial captaining experience, Scott was given a relief captain's job with Island Windjammers - to go from getting your license to captain is virtually unheard of in this industry, and they knowingly took a chance on him.  But he did - and continues to do - an excellent job so it all worked out.

Getting a captain's license is not easy - mostly because of all the paperwork and miles you must have - there are a couple ways; either via USCG or RYA.  Scott carries his 200 ton USCG license.  You need to have sailed a LOT of nautical miles on a LOT of boats in order to obtain that.  There is a tremendous amount of paperwork involved.  I wrote about it here.

You also need to pass the USCG captains test (not sure what it's called) - and this is a very long test with a lot of questions.  Some people buy the study guides and self- teach, but we'd recommend taking a class.  That's what Scott did - it was a significant investment, costing us about $5,000.00 when all was said and done.

Aside from the practicalities - what really got Scott that job was his professional demeanor and his PERSISTENCE.  He never gave up and just kept pressing forward.  It was a stressful time for us and many would have thrown in the towel along the road of getting to the point he did,  but he pressed on and was SUPER determined.  And, again, we got REALLY lucky.

As for writing, I haven't gone forward with it as a way to make a living.  It makes us beer money.  I suppose I could pursue it more aggressively, but really - it's very hard to make an income this way and it would require me to spend even MORE time at the computer than I already do (and it's a lot).  What we DO get are sponsorships, which have saved us thousands and this is because we have a well-read blog that gets well over 1,000 visitors and 5K page views a day."

2) "The challenge with making money while cruising, for us, is the fact that it forces us to stop for 4-6 weeks at a time when Scott is working.  This, in turn, means time away from each other - which is very hard (considering we have a toddler) and it has also meant that we put ourselves on a "schedule" in order for him to be where he needs to be to catch a flight.  Cruising with a timeline is not advisable and we've been stuck and/or gone out in weather we wouldn't normally have in order to get to point "A" so Scott could report to work.  Despite this, it worked very well for us and we were very grateful to have the income (it made cruising so much nicer for us since we always had a stream and it was more than enough to keep us afloat without us having to dip into our savings for anything other than big repairs/purchases) - but the time away and long breaks from cruising were hard.  We are currently working on a way to cruise without having to do this by focusing on some passive income streams...stay tuned.

The challenge with making money writing is a) not really making any money (haha!) and b) the time it takes.  I spend a tremendous amount of time on the computer; writing, answering email, editing photos, talking to sponsors and it is very challenging to balance this.  It is work I LOVE so I can get stuck in a computer rut for hours at a time, but Scott and Isla also want to spend time with me and, of course, I want to enjoy the islands and experiences I write about.  I think I spend more time on our blog than the average cruising blogger - and, for some, this amount of work would probably not be worth it.  Not to mention relying on sketchy internet can be tough.  But, really, the biggest challenge for me is finding a work/life balance as I could write for hours and hours and hours if left to my own devices...This past year I decided to stop forcing myself to post daily and only write when I truly felt moved to.  This helped a lot.  I also force myself to unplug from time to time, which also helps."

Take home message for becoming a sailor & working captain while cruising: Be persistent, work hard and make an investment in training.

Paul and Sheryl Shard from Distant Shores: Paul and Sheryl have an extensive resume that includes building their own cruising boat (they now cruise on their second Southerly), cruising since the late 1980's, authoring best selling books, and producing/filming many sailing related films, including their popular television series Distant Shores. Ironically, they are presenting a seminar titled "Earning while Cruising" at the upcoming Strictly Sail show in Chicago. If you'll be at the show on Friday, January 24, 2014, I encourage you to attend and hear firsthand how Paul and Sheryl have continued to earn a living while cruising to far off destinations. You can follow the Shards' adventures, read informative articles, and download all 117 episodes of the Distant Shores sailing adventure TV series at DistantShores.ca.

Here’s how Paul and Sheryl answered my 2 questions about earning money while cruising by working as filmmakers:

1) "The skills required for making money filming a television series are being able to: envision an appealing story, capture it beautifully and creatively on film/video using broadcast quality camera and audio equipment, script interesting narration, and finding a good distributor to get your shows on the air to the right audience. As with any profession it requires training, practice and experimentation before anyone will pay you for your work. However, these days with YouTube etc., there are  more platforms for showing your work, getting constructive feedback and earning money through TV and video production."

2) "The biggest challenge is breaking into the market. It takes time and money. Paul and I self-funded the first documentary we filmed, Call of the Ocean, which Discovery Channel licensed eventually after we shopped it around to various networks. We also self-funded the pilot episodes of both our TV series, Exploring Under Sail and Distant Shores. But it paid off. Our work in television has covered the costs of our cruising lifestyle for many years now and it is very satisfying to hear from people all over the world (Distant Shores is broadcast worldwide in 24 languages) that they are inspired by the shows and are learning to sail or are making plans to do some cruising."

Take home message for profitable filming while cruising: Practice, experiment with creativity, and consider a self-funded initial project to get noticed.

You can take solace knowing that each of the above methods are proven by experienced, veteran cruisers. Clearly there are still many more methods for earning money while cruising and I've only scratched the surface with this post. For example, Mike and Rebecca from Zero to Cruising have recently begun managing and operating a charter sailboat after having spent multiple seasons cruising the Caribbean on their own sailboat. They're insanely busy with this new endeavor, but it's a good kind of busy that allows them to continue the lifestyle they love - sailing and living in the Caribbean. Brian from s/v Delos also wrote a recent blog post about how they afford to sail that includes some excellent tips and great ideas for working while cruising.

While we aren't currently cruising, I've proven to myself that it's possible to make money by writing about sailing, as evidenced by this blog (I was paid for writing all of the posts in the "Sailing Stories" tab at the top of this page). I've also had some success with generating "passive" (total misnomer!) income by developing and managing a handful of other websites in addition to SailFarLiveFree.com.

The point of all this is that you don't need to be independently wealthy to go voyaging on a sailboat. If you're persistent, determined and able to tap into your core skills you can make it come together out in the blue yonder. And don't forget Sterling Hayden's advice about avoiding routine and the dangers of clinging to security!

Know of other "working while cruising" success stories? Share them in the comments below!


  1. What a great post and wonderful insight from all. I think this is the #1 question for many of us with the dream of cruising full-time. Or at least those of us without unlimited cruising funds. ;) We will be trying to pull in a few extra $ here and there with current gigs we already have in place (freelance graphic design/photography, that sort of thing). -Kim, s/v LAHO

  2. Anonymous24 January

    Nice post. How did you make those awesome images?

  3. Great post. We're planning on cutting the dock lines in a couple years. Hopefully our retirement will be enough but may need to subsidize. Love love the photos!! Did you use a photoshop action to create them?

    1. Thanks Carolyn. The photos are my own, modified using the Tangled FX app for iOS.

  4. Anonymous13 June

    I love the pictures

  5. Just listened to it David...great job! This one is packed with good ideas.

  6. Awesome article. We've got yet another story/idea/experience to share: I teach yoga retreats, workshops and classes along our cruising route (yoga teacher, skipper, mum) and hubby is an account and works for clients on line from the boat a few hours every day. So far so good well into our second year of cruising. As long as you follow your heart, are willing to learn and reinvente yourself every day, are active (ia not lazy) and a bit switched on about making your dream a reality and your passions your guiding beacon in life... It's bound to happen! xx


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