Imagine escaping the daily routine of work, the long commute, the corporate life, the grey skies… What if you were paid to go sailing, or paid while you were sailing? Is that an impossible dream? Not any more.

A wave of people are turning their backs on traditional, linear careers and the long wait for financial freedom to take a break or go sailing indefinitely. They have decided to downsize, go travelling, perhaps volunteering, and live a simpler, freer life. But they are quite different to the impecunious sailing nomads of the 1960s and 1970s. These highly educated professionals are cruising in comparative comfort.

If you’re smart – and most of these thirtysomething and fortysomething digital natives are smart and skilled – life on board can be turned into a robust business model, one that offers quality family time, a better work/life balance, and maybe a more meaningful existence into the bargain.

If your aim is mainly to get a fat executive salary for being on a yacht you can get that too – join the superyacht industry. But make no mistake: that route is hard work with long hours and can be extremely limiting; you never get to make the important decisions about where you go or when.

So, for the purposes of this feature, we’re assuming ‘paid to go sailing’ means being master and commander of your own yacht, going where you please and (more or less) when you fancy.

Elayna Carausu (above) and her partner Riley Whitelum (below) have built up a huge following with their Sailing La Vagabonde lifestyle videos

Start a sailing vlog

The means of making money while cruising have diversified in recent years thanks principally to the rise of remote or agile working, and the success of fund-me platforms.

Creative work is being revalued via new platforms. If you haven’t yet explored Patreon, take a look. This is the principal fund-me platform being used by cruisers, and the most popular product is YouTube video logs or podcasts. Creators invite donors to pay according to a tiered structure – larger donations for some exclusive merchandise and engagement.

Some creators have established huge followings and make a surprisingly good living. One of the earliest and best of these is Sailing SV Delos, a core group of four very media-savvy people cruising on an Amel Super Maramu. They make nearly $14,000 a video from 1,800 paying donors, and can create up to four episodes a month.

Sailing La Vagabonde is another now famous vlog channel. Riley Whitelum’s and Elayna Carausu’s travel and lifestyle videos have a huge following and, with 1,800 paying patrons, they earn just shy of $10,000 per episode. They recently got a new yacht by leasing a new Outremer catamaran – this is a serious business.

Running your own sailing vlog isn’t all fun and games

These famous vloggers have spawned around 400 copycat channels, and some of these younger vloggers have serious financial commitments including hefty marine mortgages.

Video documentaries can pay, but it takes a long time to build up a following, requires a solid understanding of social media and intensive daily work on engagement – and it helps if you are young, fit and look spectacular in a bikini! A thick skin helps too – some online commentators are unkind.

As carefree as these videos might look, this can turn into a full-time job: the ‘adventures’ need storyboarding, shooting and a huge amount of editing time. If the episodes are frequent, you are also tied regularly to locations with good wi-fi/bandwidth.

Fund-me platforms are beginning to rejuvenate all kinds of creative art that digital media previously decimated. Patreon’s high earning ideas range from craft videos to a daily newsletter inspired by the Bible, and a US political podcast.

Perhaps some of your knowledge or work skills could be transferrable to an onboard life. Are you a teacher, a translator, a business coach, a designer or illustrator? Those skills can be marketed. Or you could work freelance to pay the bills.

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Generally, the more freedom and free time you’re after, the lower the potential income. But it can be possible to earn enough money to go sailing, and enjoy it.

Some of those we interviewed admit they work harder than they did in their old desk job, and for less money, but had much greater fulfillment and satisfaction. It’s important to weigh that up, too.

The revolution in working from home has opened up many new opportunities at every point in our careers. The question is: are you ready to disrupt your life?

Are you prepared to take the plunge? Photo: Kristi Wilson

One couple who did just that are Tasha and Ryan Hacker. In 2015 they sold their education business and purchased a new Fontaine Pajot Helia 44, which they named Cheeky Monkey. They picked up their new cruising boat in La Rochelle, France, and over the next 18 months sailed her across the Atlantic to the Caribbean, through the Panama canal, and then to French Polynesia.

Tasha turned to film-making and started a YouTube channel called Chase the Story. Although she had no prior experience as a film-maker, she had a number of transferrable skills such as marketing and communication which allowed her to swiftly grow her audience and increase exposure.

Tasha had three main revenue streams: YouTube (via Google AdWords, and Patreon), which earned anywhere from $200 to $3,000 per month; writing, which earned between $250 and $1,000 per piece in popular magazines; and earnings from investments made following the sale of their company.

Tasha and Ryan Hacker fund their cruising lifestyle aboard Cheeky Monkey with work in creative media. Photo: Kristi Wilson

For Tasha the motivation for turning to film-making was not simply to fund their cruising lifestyle:

“I enjoy having a creative or professional incentive to keep my mind busy, active and sharp.” Being a YouTuber provided that discipline, while allowing her creative side to flourish.

However, there were compromises, such as the constant need to find good internet connections.

For those considering turning to YouTube or writing to fund an alternative lifestyle, Tasha has some advice: “If you love writing or film-making, and then publish them online, the money will follow and it won’t seem like a burden or a chore. But if the primary motivation is money, and you don’t love the creative process – as in, you don’t love sitting in front of a computer for hours on end while in a beautiful harbour – it will be a very difficult way to fund your cruising. It takes a long time to build an audience, and the love is what keeps you going even when the money isn’t coming in.”

Petter and Octavia Bergman live aboard their Hunter 44DS and write about their adventures on svbellamarina.com

Work from onboard

Petter and Octavia Bergman took a sailing class 14 years ago and instantly fell in love with the sport. Soon after they bought their liveaboard boat, a Hunter 44DS SV Bella Marina. They subsequently took a one-year sabbatical to cruise the Pacific coast of the USA and Mexico before settling in Silicon Valley. However, they desperately missed the cruising lifestyle, and immediately began formulating a plan that would allow them to combine their successful careers in technology with cruising.

While Octavia returned to work as a software executive and Petter did contract work building software products, they began to develop their own idea for a business that they could run while cruising: boat management software built by boaters for boaters, that they called Quartermaster. They hope in future this will provide enough income to support their lifestyle, but while it’s growing Octavia continues her consultancy work from the boat.

They also have an investment property, which provides rental income. They find that their monthly income varies greatly between $1,000 per month, to $10,000
per month, depending on the consulting engagements Octavia takes on.

For the past two years they have combined working remotely and running their business with cruising, and are currently in Hawaii preparing for a passage to the South Pacific. Octavia compares it favourably to their “old corporate work-life balance, which was non-existent”, but says that working requires them to stay in certain places for longer as they are dependent on accessing good internet.

Petter and Octavia also find they have less time for fun activities and boat maintenance compared with other non-working cruisers. But they strongly believe that despite the drawbacks, they have made the right decision.

“This lifestyle allows us to be cruising and travelling and enjoying beautiful sunsets and clear waters before being retired.

“Alternative lifestyles are becoming acceptable both in society and the workplace. We are all connected and there is internet on every rock out there. Why not take advantage of it?”

Mia Karlsson and Andy Schell take time out on a tiny island off St Thomas

Set up a part-time sailing business

American Andy Schell and Mia Karlsson, his Swedish wife, both in their thirties, decided to make their business fit the lifestyle they want. They run adventure charters, with a particular emphasis on passing on their expertise and love of the sea, and Andy has a large following for his regular podcast ‘On the Wind’.

“We take paying crew on offshore sailing passages
on our 1972 S&S Swan 48 Isbjörn. Each season consists
of an offshore passage calendar that we publish on 59-north.com, usually two years in advance, so we get to decide when and where we sail. This amounts to about 10,000 ocean miles per year over the course of about ten passages, each about 7-21 days,” explains Andy.

“We set out with a few goals: make a business where work doesn’t feel like ‘work’; earn enough to be happy, but never make it purely about money; live a simple, inexpensive lifestyle; and have the free time to pursue personal passions and spend quality time with family and friends.

“Ours is a ‘lifestyle’ business for sure – nobody’s getting rich doing it, and it’s not scalable in the same way a tech business is. I want to spend my life doing what I love, so instead of working in a job just to make money, then retire and pursue that passion, I’m skipping the middle part and making a living through sailing.

“We started the business plan backwards, in a way: there is lots of research that suggests happiness increases as income increases, but only up to about $70,000 per family per year.

Isbjörn and crew driving north from Fair Isle to Shetland

“So we used that as a target number, and tried to figure out how few passages we’d need to run to hit that number as profit, leaving a little margin for unsold bunks, unforeseen maintenance, etc.

“We bought a 45-year-old boat, and have replaced basically every bolt-on system. We got the boat relatively cheap – $130,000 – and since have put in at least $150,000 more on refit items. But, come this spring when she launches after a big nine-month layup and refit, she will essentially be brand-new from a systems standpoint, and we’ve got an all-time great ocean sailing boat, fully out fitted exactly as we want her, for $300,000.

“On the income side, we’ve ended up doing better than that initial $70,000 a year projection. In addition to the passages we offer, I host a popular podcast called ‘On the Wind,’ that makes its own revenue through sponsorships and donations (and, accidentally, is our primary marketing outlet; we estimate that about 75 per cent of our paying crew are fans of the podcast first). And, we host a few workshops in the fall in Annapolis, plus write the occasional article for magazines.

“All told, we make just under $200,000 a year, though with the huge refit expenses on the boat, we’ve only cleared about $40,000 in profit in 2016 and 2017. But that profit will certainly grow.

“We budget about $40,000 a year for maintenance, insurance, berthing fees etc. In addition, we have a fund for new sails every 50-60,000 miles, or five to six years, which total $25,000, but the back-end of the business has very low expenses, as everything is paperless and cloud-based, and we have no physical office.

“Ironically, sailing as a living is not really freedom – yes, we’re free to choose where and when we sail, but once we commit, we’re stuck to that plan. The freedom part comes in actually when we’re not on the boat. In our off season, besides running the back-end of the business and producing my podcast, we’re free to do what we want and have tons of free time.

“What scares me most is having a family. When we do have kids, I won’t want to go offshore anymore. We’ll have to take turns on the boat. But our passion has been shared from the start with us, so we’re optimistic.”

Matt and Lucy Wilcox aboard their Lagoon 380 S2 Independence

Freelance from your boat

Matt and Lucy Wilcox have been sailing for 14 years. Two years ago they bought a 2005 Lagoon 380 to cruise the US East Coast and the Bahamas.

The plan was to live off savings, then head back to work, but when the time came to return to their land-based lives they found they couldn’t give up their cruising lifestyle aboard Independence so instead made the transition to becoming digital nomads.

Lucy had previously worked for a university, teaching courses online, and secured a similar job teaching English online to Chinese students. Matt, meanwhile, freelances as a photographer and graphic designer, bidding for work using freelancing websites. Additionally, they are both cruising editors and photographers for the Bahamas Waterways Guide, and both undertake freelance writing work. This results in a 20-hour working week for each of them, with a combined income of US$2,400 per month.

Lack of mobile phone service can sometimes mean that certain areas can’t be explored as much as they would otherwise wish. Additionally, passage plans have to take into account Lucy’s online classes, which start at 0500.

During their two days off per week, they move the boat to another location, explore or simply relax. When they have the time and inclination, particularly if they are port-bound due to poor weather, they are able to increase their workload. When they are busy sailing, doing boat work, or have poor phone service, they are able to drop down their workload.

Lucy says: “Working part-time while cruising has actually brought more satisfaction and balance to our lives. We earn about 25 per cent of our land-based earnings, but we’ve never felt more successful. Working and cruising has been a win-win for us.”

Rubicon 3’s yachts include Oriole (foreground) and Hummingbird

Start a full-time sailing business

Bruce Jacobs and Rachael Sprot decided to make sailing their business when they set up Rubicon 3. The business partners now have three yachts. This is a great example of the small but growing number of very professional, targeted, social-savvy adventure sailing businesses.

“Rachael and myself come from very different backgrounds. She is the daughter of a professional sailor and has worked as a sailor all her professional life. I spent 12 years in industry, working in marketing and product development,” says Jacobs.

“In 2012, we heard that Hummingbird (Blackadder, as she then was) was being sold by Clipper Ventures and begged and borrowed to buy her.

“I knew without doubt that we could outmarket the rest of the industry. But getting the customers was only half the battle.

“For five years now, neither of us has worked less than a 60-hour week and it is often far higher than that. This is partly because we are also committed to building a new type of sailing company that gives professional sailors proper training, pay and job security.”

Rachael Sprot at the office, helming one of the business’s yachts, Hummingbird

The work-life balance is something that should concern anyone thinking of making a leap to a sailing business from another career, thinks Jacobs.

“We sailed almost non-stop for the first two years, and actually it was pretty tough with family life as I was newly married and had a new baby. But now we skipper probably two trips a year as the admin and management side has become a full time job for both of us.

“When you are self-employed the work/life balance is different. There is far less ‘free’ time than before but there’s also far more motivation and satisfaction.”

As for the money, he says: “We spent five years paying ourselves very little (nothing at the start) so there is quite a bit of catching up to do. We pay ourselves enough now to pay the rent and bills, and that is fine. Any spare goes back into the business.

“I would urge huge caution to anyone thinking of trading in their current situation for something quite different. It’s easy to find a hobby is not the same as spending every day of your life doing it, and what may have been a real love can become a chore. Sailing is a very badly paid industry and while it can be a lovely thing to do for a while, it is a rare person who makes a long term living from it.

“My advice is to plan a career. How will you progress? What skills will you need to learn, what courses will you need to take, where will you be in 20 years from now? If you can’t answer that or don’t like the answer it may be better to keep sailing as your hobby.”