7 ways to finance your sailing adventure

After an exciting beginning, long term cruising can become a fight for financial survival.

During some time spent cruising I observed some specific behaviors and strategies that people adopt to fuel the sailing dream.

I decided to classify this economical behaviors drawing 7 cruising types. Any attempt to classify individuals in typologies always carry the risk of oversimplification and generalization. In real life cruisers often adopt a cross-pollination approach, suitable case by case.

I originally found 5 categories that I think are classic ones, but then I felt the need to add 2 more, because times are changing, and, believe it or not, we are evolving.

Here are 7 types of cruisers divided into different economical behavior:

1. Harbor rats

A group of very dedicated and skilled cruisers, with budget limitations that enhances creative thinking. I saw some of them floating the hull above the waterline using truck tyre tubes and performing other crazy low cost, low-tech solutions. Their boats are put together with a collection of mad max type dumpster dived items. They soon get skilled enough to perform sketchy boat work for clueless and/or broken sailors that pay in boat parts, favors like car rides, boat sitting or food and shelter. They avoid sailing to countries with expensive cruising fees. If posssible they get to the point of deceiving officials by forging clearance papers themselves if that helps them save some bucks. 

2. Comfy retired or semi retired folks 

Easy spotted by their complex and heavy as hell stern arches and bimini structures that costed not only money but human lives during the fabrication. They usually live off their savings and or investments with different degrees of luxury depending on the case, but generally speaking on the lower end which translates in a very good ability to keep track of expenses. They try to save money nitpicking on contractors’ work and equipment, on food vendors and taxis and they may never leave the comfort of the harbor without a spare alternator but they don’t buy an available one because it’s more expensive than “back home”. They say they will pick up one next time they fly back, which is entirely dependent on the house or financial market returns. Due to all the crap on deck and above, their boats sail poorly and with great effort until they settle, usually in a part of the world which is cheap. Internet, chinese restaurants and booze are the expenses they struggle to keep in check.

3. World charter businessmen/women

They buy a big boat thinking that it will pay itself doing off-the-beaten-track charters and in general having paying guests. They settle in a country with loose regulations and tropical features but with good enough infrastructure for the guests to be able to reach the boat and for them to enjoy their vices with a lower price tag. As there are not many places like this around they compete with other boats over customers. This drives the price down and so the returns. Costs keep raising as they have to keep the boat in good shape because otherwise guests are going to leave bad reviews on the internet. Being in places where locals paddle dugout canoes and can only sell you fish and coconuts, where shipping is either unknown or crazy slow and expensive, and if you need a mechanic you need yo fly one in does not help with boat upkeep. Logistic hassles, booking fever and, sometimes terrible guests totally undermine the healthy lifestyle they were longing for, while their boats fall apart.

4. Technomads

These are the pioneers of the internet revolution, people with a real job they could do anywhere they can be connected, even on a boat. I’ve met editors, skype english teachers, cruising consultants (I know this should not be a “real job”) coders and other tech people, that enjoy few hours of work per day on a computer in exchange of money. Their focus is to keep the infrastructure going, making sure the machines stay out of salt water or anchoring closer to the cell tower even if there the swell is good enough for surfing. Marinas and cruising destinations are chosen and rated by the internet signal quality and other close by amenities like internet cafes and libraries. They sail to nicer places only during weekends or holidays. Usually before any long passage there is a deadline panic that obstuct the passage planning routine. Finally, after the second day on passage they dream about quitting their job and find a different source of income.

5. Part-time cruisers

They are experts in packing/ unpacking the boat for long term storage, and they are a tough cookie for any yard manager. Haul out fees and collaterals are the main expense on their books, together with airfare and unnecessary compulsive shopping items, boat parts and souvenirs that fill the extra check-in bags each way. They are usually able to ratch up quite a sum during their work period that they then spend almost instantly in the first weeks of cruising. By the end of the sailing period they look a lot like the Harbor Rat type, sometimes having to borrow money to get back to work.

6. Girls and dudes with patreon accounts

These new group started to emerge when people decided that Youtube was the perfect place to quench their sailing thirst. This stalking platform is the new stage for the soap operas of the sea, with the most succesful one that even provide income for the creators. The basic idea here is that a group of “angels” (or patrons) pay upfront for a product that involve a lot of work and investment and that once released, anybody else can watch for free on youtube. So far I haven’t met many of those in the real world, just a couple, and not the superstars. Because the videos were not paying off they were also resorting to other forms of hustle to keep the finance in check. The internet makes it a bigger phenomenon than it is in real life and yet, because homo sapiens is mainly here to mimic other homo sapiens, the number of people who attempt this way is increasing. They say commercial fishermen destroy the oceans, but I think people buying and eating fish are the real culprits. Same with the vlogging: blaming the hardworking bluecollars of the camera for our inevitable loss of intelligence and taste is a form of hypocrisy. The odds for financial solvency using this approach seem pretty slim, as at the moment it pays off only to the few who can gather enough views and convince donors to pay for their videos. This challenge sometimes requires to the ones a cost in hours of work and focus on their public image that hinders a little bit the idea of traveling for fun, and to take themselves not too seriously.

7. Grifters and visionaries

It takes guts to be in this group. We are looking at a very small number of individuals that are willing to sail no matter what. To conquer donors and enablers they need a higher purpose or challenge and to look as much as possible as clueless trainwrecks doomed to fail. Stubborness and willingness to go down to the lowest possible points of human dignity seem to help as well. This is only for the very motivated ones, like Rimas and very few others. The good thing is that you don’t have to put any money in it.

Do cruisers out there recognize other type of economical behavior? If so, please let me know in the comments.

The first time I fell in love with sailing

Sailing happened to me. It was never something I was inclined to, not even interested. My first love has always been the mountains.

In Italy sailing is thought to be an activity for rich people. It is of course a prejudice, as there are ways to make it more affordable, but on average the costs are pretty high. I too fell into the power of generalization and thought that sailing was an activity exclusive to a group of snobby rich obnoxious people. Of course I was not part of this group and I preferred the cheap and harsh alpine terrain, where I hiked and sometimes skied.

The first time I step on a sailing boat it was ten years ago, aboard Bicho, a Beneteau 51 designed by German Frers, that a friend of mine recently purchased to run charters in Venezuela. Bicho was big, comfortable, elegant, and she was waiting for us on a dock in Higuerote, to take us on a cruise of Los Roques. The owner invited me and other friends to celebrate the recent purchase and the beginning of the charter activities.

Aerial view of Archipielago de Los Roques, in Venezuela

We had an overnight sail offshore in the Caribbean Sea, which during peak season of the trade winds has some serious waves, and you feel them all when they hit you on your beam.

I slept in the forward cabin, rolling left and right and sometimes finding myself in midair. Because I was not sick as other of the passengers, I had to keep the helm for  a little bit, after receiving vague instructions on how to steer a course following the compass.

Once in the protection of the islands we enjoyed a week of island hopping, sailing through flat and crystal clear waters powered by a steady breeze, and surrounded by a wonderful scenario. Sitting on the rail on the windward side of the boat I let my legs dangle off the side while keeping my sight on the liquid horizon, enjoying a sensation of peace that I grew accustomed to during these years, and yet still so hard to describe.

Sailing time aboard Bicho

Back to Good Old Europe, in the gray and busy Pianura Padana, I resumed my job of building and delivering courses for employees and manager of various companies, helping them navigate through the treacherous waters of corporate life.

A year passed by, and I enjoyed the mountains more than the ocean. I realized my dream to take a solo trip to India and explore the Himalayan regions of Kashmir and Ladakh. I also decided to move from Milan to Turin and that put me even closer to the Alps.

A fertile valley in the arid Ladakhi Mountains, in India

Until one day, serendipitously, I left it all behind and moved to sea level, again in Los Roques, where I started a new professional path that I had never thought could be suited for me.

It was only after months there that I realized how those islands were nothing but a series of very high submarine mountains, with their peaks piercing the surface of the ocean, providing beautiful beaches and habitat for marine life and humans engaged in tourism. Once again I could feel that my attraction to mountain peaks

And yet in my mind I was no sailor. I still thought of myself as a manager running a business, until one day during a period of shipyard refit for Bicho in Curaçao, I met a person that challenged this view and planted a seed that would change my life.

I was living on a gutted charter boat in the Tropical heat. Only one cabin, where I slept and kept my belongings, was left untouched. Everything else was dismantled and under reconstruction, covered in dust and grease, and littered with tools and building materials. The project was very ambitious and I was doing my best to keep it underway while the chaos was unraveling around me.

My workplace in Curaçao

In that shipyard I met a young guy who was doing the same thing, only on a smaller boat. He was fit, fun to be around and hard working, and he was outfitting his own boat to sail across the pacific to Polynesia, where he had a seasonal job as crew of a luxury Motor Yacht.

We were the two youngest people living in the yard and we quickly bonded. He had a temper and was very energetic, I am low key and relaxed, so we found a natural way to coexist. For me he was an encyclopedia of boat work and I couldn’t restrain myself from asking him about anything sailing related and observing his work.

He would also share his sea stories with me, on how he sailed that old leaky wooden racing boat, bought sight unseen, straight from Nova Scotia to Saint Martin during the winter, with a couple of backpackers that had never sailed before, or how once he got dismasted in the Caribbean Sea and decided to decline rescue and instead drifted back from where he started to fix his mast and sail again.

His stories were eye opening for a rookie like me that thought boats only meant business and plummeting bills. He also debunked some myths about sailing that I had taken as axioms, first and more important that you need a big boat to sail across oceans.

Sailing lessons underway

I immediately identified with him. He was a young guy enjoying life on a boat on the cheap, and this was a revolutionary idea for me. Beside his long sailing experience, we were not so different.

After few months of hard work in the yard and long night talks he set off solo from Curaçao, to his destiny across the ocean, but before leaving, he gave me a suggestion. He told me that Back in Los Roques there was a good old boat, perfect for me. It was a Rival 32 that his friend was selling for 10.000$. When I got back to Los Roques I quickly found the boat. It was in need of a bit of TLC but that was not so important as visions of a new life afloat were flooding my daydreaming.

There was another option, which I also took from his personal example, that had a similar price tag: to take a professional license and make sailing my new career.

I chose the second option, because I knew that eventually another boat would show up at the right time and in the right place, and I would be better prepared to take on the challenge.

At least this is how I prefer to tell the story.

The real cost of Cruising

Despite the complicated jargon and the many moving parts involved in sailing, it’s no rocket science, as some may say, and with enough practice and dedication it is possible to quickly become competent in using the wind to move through water, to navigate across oceans and near shore and to keep your vessel in good working order. However very few people seem to be out there enjoying the cruising lifestyle. That stands true even if today we benefit from a lower knowledge barrier than 30 or more years ago.

“Se fosse facile, lo farebbero tutti” says Max, a good friend of mine,talking about sailing and cruising. In English it sounds more or less like this: “If it was easy, everybody would be doing it”. I have been working on sailboats for 8 years now, but only after three years sailing on my own boat I am starting to realize what Max’s words really mean.

Despite what people who push their books, websites and youtube channels tell you, it is not for everybody. Like anything else, sailing and cruising has a cost. What I didn’t know is that is not merely a financial one. It is more complicated than that.

Sailing per se is easy. I say that because, in my humble opinion and personal experience, there is nothing too difficult about it. Despite the complicated jargon and the many moving parts involved in sailing, it’s no rocket science, as some may say, and with enough practice and dedication it is possible to quickly become competent in using the wind to move through water, to navigate across oceans and near shore and to keep your vessel in good working order

However very few people seem to be out there enjoying the cruising lifestyle. That stands true even if today we benefit from a lower knowledge barrier than 30 or more years ago, thanks to the GPS, reliable auxiliary propulsion, step-to-step DIY resources like youtube, to name some technological improvements that make sailing more accessible. It still takes effort and dedication to learn how to sail, but that’s the easy, even fun part.

The costs of sailing

A recent article by Fiona McGlynn on BoatUS magazine takes a wide look into this subject while trying to answer the question why the so-called Millenials don’t own sailboats as much as the same age group did in the past. This arbitrary label apparently is stretching its ends and now I fall in this group too.

Like many times when you focus on age groups there is the tendency to fall into stereotypes and prejudice (see ageism), but I think the author did a good job collecting different voices on the matter, drawing a comprehensive picture of the phenomenon, and leaving open questions.

According to the article, the main reason for fewer young boat owners is a financial one. Today salaries are simply not enough to take on an expensive hobby like sailing. But despite of this economical barrier, we still meet younger people on the water that get away with the costs of ownerships adopting a shoestring approach.

This was definitely what we did when we bought Tranquility. We bought the boat that we could afford at the moment, cash, and we slowly put her and ourselves in the water, instead of taking a loan or waiting to save a huge cruising budget. We ended up with a small old boat, but at least we could pay for it.

Unfortunately, there are also other dimensions than money that are easily overlooked, and those constitute nonetheless a cost that can be as limiting as the financial one.


The workplace is becoming more and more competitive as the adult population increases and work longer in life. Having a good job today could be a good enough reason to stick with it. Successful careers entice people with status, income and a sense of a higher purpose. Workers without access to good jobs live with the expectation of finally landing one and focus obsessively on their career path and skill set, to the point to make it unthinkable to “lose ground” joining a more time consuming sailing lifestyle, like cruising your own boat on a sabbatical. The time we pass in school to develop these skills also extended, and an activity like sailing can be hard to justify in the overall picture, especially at a younger age, when students are challenged to think a bout their future.


The Fear Of Missing Out while cruising means much more than losing the last trend or gossip on websites and Social Media because of limited internet access. It means fear of missing the joyful and sad events of one’s closest family and friends. Cruising distant destinations puts more obstacles between family visits, that require expensive airfare and logistic hassles. I sometimes regret not being able to participate to a group vacation, celebrate births, being close to beloved ones in face of deaths or personal needs, attending family celebrations like Thanksgiving or Christmas, or simply reaching out to a friend for a chat and a bite of food. While traveling it is always possible to meet and enjoy the company of interesting like-minded people, but the disconnection from family and friends is definitely an emotional cost of this lifestyle.


The assumption that you are able to keep your car, your apartment, health or dental insurance, retirement savings and also take off for a long distance cruise is an illusion for most. Bills and cruising are mutually exclusive. There is definitely who is able to go sailing and take care of assets as well as a safety net back home, but most of the people we meet cruising don’t have such luxury, and have to risk and sacrifice their security for an endeavor that could end in a hole in the water.
On one side this situation is a gift, because it could bring a reboot of the system, and open up space in life for new and interesting projects. On the other side there is the risk that the “economy of staying afloat” could prevent any future move for lack of funding.


There are good reasons why human beings evolved in the direction of living indoor and on land. Excessive heat or cold, light or dark, avoidance of bugs and parasites and bothersome if not dangerous wildlife, impacts from severe weather are some of the nuisances of outdoor life in general, and cruising in the specific. As you learn while cruising distant locations, this is still an inescapable reality for many people on earth, and you could learn from their example how to deal with it.

One clear example is the simple act of bathing. What we perform everyday in our home bathrooms mutates when  you step on a boat. It becomes more similar to what I learned from my grandmother’s stories. From the expectation of having pressurized heated water, you are happy when you find clean, spring water to fill your jugs.

Even if this experience can be eye-opening about the insane consumption typical of our developed societies, you find yourself thinking a lot of times about the long hot shower you can’t have, an air-conditioned room or the full collection of snacks and leftovers waiting inside a refrigerator.


Problems are the salt of life, but self-reliance on a boat that visits remote areas means being able to cope with various number of problems. I learned it the hard way myself, as I watched my hands change look when I started to use them for manual hard work, instead of just for typing on a keyboard and playing basketball. It was a painful process like most of changes in life.

On a positive note, I discovered how rewarding solving problems can be, especially if you have to find creative ways and have limited resources. It enhances self-perceived efficacy and pride. As a downside, the feeling that reality constantly put you under test and challenges generates stress that could provoke avoidance of the problem in the first place and high doses of frustration and procrastination. A boat not able to perform can be a haunting entity and diminish the pleasures of cruising. While you grow in resourcefulness and competence, you definitely go through moments of feeling stuck and unable to progress, as it appears that there is always something unexpected that has to be taken care of.


I hope my words don’t sound excessively like a whine or a plead for pity. In this blog I attempt to overcome the solitude of my own thoughts and to help the process of sense making, a process that have to pass necessarily through the difficult parts as well as the good ones.

I can assure you that overall Kate and I are doing great and we feel very fortunate about our decision. I also want to avoid depicting us as martyrs or heroes because we deal with such harsh condition. I feel very privileged for being born in a certain geographical location and family, both of which I did not chose nor I can say that I deserve. I am blessed that because of this special situation I have the opportunity to travel and to gift myself with time and new experiences.

The reason I wrote about the less desirable parts of this lifestyle is because I wanted to be honest about it. There is a tendency to depict the entire thing as an endless vacation, full of awe and unforgettable moments. Worst, there is another assumption that you can only do it if you have the money, but as I hope to have shown in this post money is not enough.

I love sailing, but I would be a liar if I tell that it’s only fun. It is expensive, uncomfortable and demanding. Part of it is fascinating, but another part feels unnecessary and masochistic at times. Everything has a price. The cruising lifestyle has its own way to charge for the experience, but we are happy to pay this price because we really like the rewards. As one of my readers wrote: “once you are hooked, there is nothing like being out there with just the wind and the waves”.