The 5 obstacles to “living the cruising dream”

living the dreamSailing towards distant horizons, visiting new countries following one’s own time is an increasing popular lifestyle, a dream at hand’s reach.

The new wave of sailing bloggers (like myself) and Youtube Sailing Channel lure a wide audience into this narrative of self-realization and discovery that helps to spring up the belief that absolutely everyone can cast off for a long term sailing adventure, and do it cheaply. In theory anyone who puts sweat and hours in, will succeed if they follow few common sense advices from the experts.

Is it really true? Can anybody leave everything behind and go sailing?

It is no longer entirely true that sailing is an exclusive playground for the very rich. Boating on a budget is a reality today thanks to the fiberglass revolution that brought us an ever increasing pack of second hand, affordable boats, still in condition to sail safely with little elbow grease.

Resourceful individuals can acquire most of the necessary knowledge to fit out a boat and teach themselves how to sail through websites and the many books available on the subject.

Present-day reliable auxiliary propulsion, GPS, AIS and other technological enhancements give some leeway to grave mistakes intrinsic to the learning journey of a beginner sailor and navigator.

Ebay, Amazon, Craigslist and marine online stores made shopping for equipment and spare parts merely a matter of clicks, delivered to the front door in no time.

All of the above is true, but still only available to a fraction of the human population. Small numbers even considering the lucky people that live in First World countries. On a global scale sailing is still the realm of the privileged.

Sure, anybody can work towards “changing mindset”, “learning the ropes”, “save money” or “become minimalist” but there are barriers that individuals may not be able to cross, even if they try hard.

Because of political and socio-economical circumstances not everybody has the access to resources and opportunities to afford the cost of cruising, even for how inexpensively it might be nowadays.

Sometimes it’s not a mere financial matter. Having to support a family member or having to deal with a delicate health condition may prevent at all one’s ability to go and “live the dream”.

cruising lifestyle


Let’s have a look to the 5 real barriers to the living the cruising dream:

  1. Health: permanent medical conditions dependent on treatment  may hinder the planning of sailing adventures. Quality health care may require expensive travel insurance or not being an option in certain countries of the World. Medications may be difficult to buy abroad or even illegal to bring in.
  2. Finances: access to a salary paid with a stable, high valued currency is a prerequisite to afford the sailing lifestyle. Very few currencies hold enough value on the global market to make the exchange with foreign currency possible. The ability to generate savings for the “cruising kitty” is influenced by the level of personal debt and the access to well paid compensation. These conditions are highly dependent on the simple luck of where one was born.
  3. Country of origin: the recent US ban on Muslim countries is a clear evidence that being born in a specific geographical area is more important than who you really are. Not all passports are created equal and grant access to the necessary visitor visas. It’s a privilege afforded to relatively few countries in the World.
  4. Relationships: being surrounded by family and friends that understand your decision and can financially and emotionally support themselves is a great help in making the decision to leave it all behind. For how individualistic going sailing might appear, it’s the result of the help and generosity of many people along the way, especially for beginners.
  5. Culture: not all cultures celebrate the freedom of pursuing one own’s dream regarding family and group goals as more important. Collectivistic cultures may not support the goal of long distance travel and consider it a threat to family and group cohesion and goals.


For some people sailing is a hard way to make a living rather than a leisure activity

For some people sailing is a hard way to make a living rather than a leisure activity

The role of chance in successful cruising stories

People who sail for pleasure are blessed by life circumstances that are out one’s control, and mostly determined by luck. As Nobel Prize Daniel Kahneman claimed in his book “Thinking fast and slow”,

“We tend to underestimate the role of chance in events.”

This may be explained by the hindsight bias, the inclination to see past events as predictable. The overconfidence that our own skills play a greater role over contextual and random events in our success arise as consequence of this cognitive fallacy.

In face of equal effort, some people get to enjoy the cruising life, simply because of the role of small and random advantages. Realizing that initial advantages plays a much greater role than we think is important to raise awareness of diversity between people in regards to access to opportunities.

Banalizing the “living the dream” adagio, pretending that everybody out there can do it and that only our mind is in the way, is not only unjust towards people who face serious obstacles (and wish different), it’s also unrealistic and biased by privilege and social dominance. Not seeing the role of chance and privilege make us less sympathetic and blinds us to systemic disadvantages.

Awareness of one own’s possibilities

All that said, even people in the most difficult situation have a degree of freedom they could work on. Luck and chance are not the only factors that shape the type of population that get to enjoy cruising and voyaging, and pulling off the rat race would not happen without the proverbial hard work, perseverance and sacrifice.

If you are already thinking about casting off to go sailing you probably already overcome some or all of those 5. You still have work to do, but your odds are definitely promising. Now it’s the time to work hard on planning, finances, type of boat, downsizing, mental attitude, focus and skills. Knowing what really put you there in the first place make all the other limitations and difficulties look like smaller barriers.

Recognizing to have been born under a lucky star may make you more grateful, more compassionate to others and feeling the need to pay forward some of the unsolicited help that came your way.

IF you have the opportunity to go sailing, WHY NOT?


6 thoughts on “The 5 obstacles to “living the cruising dream”

  1. Carol Reed says:

    I did teach myself and took off in 87 for 13 years. I was in 59 countries (before you tube and cell phones) for extended periods of time. This was by far the best education I have ever managed to get, and I am still happy that I made the decision. I love your list. The only thing I would add is a half way decent IQ, because there are always going to be times that you need it, and being able to figure out something that works better than what you found in the books makes a big difference.
    I wish anyone following in my wake a fabulous life.

    1. says:

      Thank you for your story Carol. I am wondering how you adapted to go back to life on land. Today I had to drive in traffic after a while and it was traumatic.

  2. Spencer smith says:

    Did you forget “practice”? Don’t bet the farm on something you haven’t tried already: be crew on an offshore delivery, charter in a new and challenging place. Do that and more before you make up your mind to cut loose from shore.

    1. fabiobrunazzi says:

      That’s a wise suggestion. Thank you Spencer.

    2. fabiobrunazzi says:

      I started this website to get back to my previous profession, organizational psychologist and to merge it with my present one, professional sailor. If you are interested in more “nautical” tales, check out

    3. says:

      Yes, Spencer, practice have an important role once one has the possibility to go sailing. Thanks for your comment.

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