/15 Ways To Avoid Failure When Becoming A Liveaboard Cruiser

15 Ways To Avoid Failure When Becoming A Liveaboard Cruiser

What factors contribute to the success or failure of becoming a liveaboard cruiser? Over this past year, we’ve seen an increase in couples and families that make the leap into liveaboard cruising only to quickly determine it was the wrong choice. 
Some have risked everything, having sold their home, car, and possessions. Not only did they discover that sailing wasn’t for them but they had nothing to go ‘home’ to when their chips were down. The best case scenario for failure is a substantial loss of time and money and a big dent to the ego. 
Gain invaluable experience before you spend time and money. Join us on Britican. Click for more information.
On the flip side, is there such thing as failure? 
I ultimately think that those who set out to live the liveaboard life and don’t make it happen are in no, way, shape or form ‘failures’. They simply took a chance, discovered they didn’t like something and will give something else a go (and most likely get closer to ‘success’ with their next choice). We’re all trying to figure out what direction to go in.
The more we fail the quicker we learn what we want rather than what we don’t want.
However, if you’re going to spend a heck of a lot of time, money and emotional energy getting a boat and heading out to sea I’d really like for you to not only make it happen but to enjoy the journey AND the resulting new lifestyle. 
Becoming a liveaboard cruising sailor is incredible. Every day I enjoy warm temperatures. I look out at sandy beaches, tall palm trees, and the deep blue sea. My amazing family and friends surround me. I spend loads of time with my husband and daughter – and I love it! I eat amazingly delicious meals. I can go swimming anytime I want. My social life is fulfilling and fun. Life just seems to flow. And I get to travel around the world seeing new lands. I honestly couldn’t imagine doing anything else other than living and cruising around on our lovely boat, Britican. 
Yes. The cruising life can be out-of-this-world. It can also be very difficult. In fact, it can be so difficult that some people/families don’t make it through the transition. 
But before we get ahead of ourselves, what exactly is a liveaboard cruiser? 
A liveaboard cruiser is someone who spends long durations or even lives full-time on a boat. A liveaboard may live in a marina or he/she/they could spend time sailing from one destination to the next. A liveaboard could spend summers in the NE coast of America and winters in the Bahamas or they could be circumnavigating the world. 
So – what makes or breaks the plans for someone to successfully transition into the liveaboard lifestyle? Here are my thoughts – they’re in no particular order. My hope is that you see where people get it wrong and can then make an effort to avoid the most common pitfalls. Once you’ve finished reading through these, please leave me a comment below on your thoughts. 
Check out views like these on Britican. Click the picture to learn how.
#1 An ineffective or inefficient setting of priorities.
We see newcomers spending months and even years getting the boat ready for the grand adventure yet failing to actually go out sailing. Especially when we’re in marinas, we meet couple after couple that spends time, energy and heaps of money fitting out their boat.
In most cases, these couples end up leaving the marina only to return after the first voyage or first planned trip. 
What often happens is that the newcomers plan their first trip to be a long one. They then end up in ‘bad’ weather, or something ‘major’ breaks and one or more of the crew (especially if kids are on board) get scared. Without gaining experience in smaller steps and building upon those experiences, the newcomers try to be seasoned liveaboards from day one.  
Think about it this way… Imagine someone that wants to run a marathon. Envision that they buy the clothes, get their nutritional regime set up, chooses the right marathon to enter, have a training schedule and then fail to go out running every day. How will they do when race day arrives?!
If you buy a boat and don’t take it sailing, at least weekly for several months, you’re not building up your knowledge and experience to handle longer passages. Furthermore, you’re not testing the boat to see what’s working and what’s not. 
Some of the major priorities of becoming a liveaboard cruiser are as follows:
Getting the right boat (to be explained later)
Making sure the boat is seaworthy and all safety systems are in place
Going out sailing for even an hour or a few hours throughout the week, every week, until finally going further afield. 
Notice that getting the latest GPS or ensuring the pillows match the interior colors is not on the list of priorities. 
Learn how to anchor, pick up a mooring ball and more on Britican. Click the image for more info.
#2 Sights on the wrong goal – Sailing as a means to an end or a ‘Bucket List’ tick.
The people I’ve met that have gotten into sailing as a means to an end don’t seem to last very long. I imagine that they think sailing is an inexpensive way to see the world. They also think it’s not that difficult. 
Owning a boat, maintaining a boat and being a foreigner in every country you visit is not inexpensive. It’s not easy. Furthermore, getting from A to B involves quite a lot of work. (And actually, you usually don’t get to B…you end up at D or E). 
To truly embrace the liveaboard lifestyle you have to have a love for sailing. Now that doesn’t mean you don’t get seasick or love every passage. I get seasick often but overall the amount of time I’m seasick pales into insignificance when considering the benefits of the whole package. I love sailing. I love everything about boats, the sea, the lifestyle. The traveling part is more of a cherry on top rather than the main dessert.
The key thing to ‘get’ is that it’s a lifestyle you’re transitioning into…not simply a way to see the world. If you want to see the world it would be far easier and cheaper to backpack your way around 😉
#3 Not being able to accept and embrace the status of ‘newbie’ at an older age.
By the time we’re older we all perfectionists. When we do things, we do things to the best of our ability and are usually satisfied with our results.
When transitioning to be a liveaboard cruiser there’s a hefty learning curve. If you know something about sailing or are good with your hands or have a background in boat systems the transition is easier but it’s not easy.
You’ll mess up. You’ll hit something or run aground. Things will break and you will not know how to fix them. You’ll get ripped off by a boat yard.
What’s important to remember is that you’ll have a series of small failures but they will lead to amazing successes. You do, however, have to allow yourself to fail in the first place.
Being on a boat will humble you. Be prepared to be humbled and you’ll find success. Refuse to be wrong or let your ego get in the way and you’re going to seriously struggle. 

Join us on Britican for a week-long liveaboard sailing experience. Each experience is created bespoke to you/your partners/your families needs. Learn how to sail at night, plan passages, and/or book into foreign countries AND enjoy the sun, sand and sea of the tropics. We teach singles, couples and families what it truly is like to live the liveaboard lifestyle. Let us help you to make your dreams come true! Click here for more information. And find out about our Members Only Club too.
#4 Choosing the wrong boat.
We’ve seen an increase in people buying the wrong boat for their cruising intentions or simply buying a lemon.
Some boats are made for sailing in the oceans and others are not. Some are more practical for the Bahamas and others are better for the Southern Ocean. Many are good for kids and some are really not safe at all. The list goes on and on. 
Let me give you an example.
Just yesterday a lovely guy, named Tom, from Toronto came up to me while anchored in Antigua. 
Tom explained that he took his 39’ Beneteau (a good size boat for Lake Ontario) down from the States to the Caribbean (small boat for the sea). He said it’s the very worst boat you could ever be in on an Ocean. He’s been in, what felt like a washing machine, the whole way. Beneteau’s are light displacement boats – unlike heavy displacement boats they get tossed around and the journey is possible but can be quite uncomfortable. 
And Tom then stated, ‘Also, I do like my wife, but we each sleep in separate rooms because there’s just not enough space.’ 
The good news about Tom, however, is that he now knows what he doesn’t want. 
Tom managed to sell his Beneteau and is heading back to Toronto to sell his house and buy the right boat (for his cruising plans and necessary comfort requirements). He’s been bitten by the liveaboard cruising bug and now knows a heck of a lot more now than he did before. 
Fortunate for him, he dipped his toes in the water before selling everything. He bought a ‘small’ boat and got out on the ocean to gain some experience and an insight into the lifestyle. Tom gained invaluable experience and now knows it’s the right lifestyle but he’s not got to find the right boat for his cruising intentions. Tom is now looking for a heavy displacement boat with more room to enjoy sleeping next to his wife 😉
And what about flat out choosing the wrong boat – a lemon? 
Some boats are flat out junk. They’ll never actually sail without something breaking or falling apart or off. Do you remember the movie ‘The Money Pit,’ where Tom Hanks and I think it was Shelly Long buy a house and it just falls apart? Well, that’s what having the right boat is like. YES – even when you have the right boat, it’s constantly falling apart. If you get the wrong boat you simply don’t have a chance. 
When buying a boat there are definite ways to increase your likelihood for a good boat. 
This is how I think you should reduce your chances of buying a lemon:
If using a broker, it’s important to find one that is not representing the seller of the boat. So, instead of calling up the broker on Yacht World and initiating a possible purchase, you first find a broker that comes highly recommended (from a source independent of the boat). 
Once you find a quality broker, you ask the broker to find what you’re looking for. And then the broker will call up the broker on Yacht World and work on your behalf to ensure the process works for your benefit (and not detriment). As a guideline, to use the services of a broker the price of the boat needs to be in the general region of $100,000 or above. 
Brokers make a percentage of the boat sale. For all the time and effort that good brokers put in, anything under $100k won’t cover their costs. 
After working with the broker to create a strategy on what you want, why you want it in addition to discussing timings and budget, you can start to narrow down your options (with the help of your broker). Eventually, you find the boat that has the highest potential to be the ‘right’ boat. 
After asking the key questions to weed out duds, it’s time to move forward in the process.
If you’re not using a broker, make sure to get my guide, Pre-Viewing Questions, to know what to ask prior to a personal viewing. And then go view the boat using my Viewing Boats to Buy guide. You should get this guide no matter what you do – it will help you know what red flags to look out for when viewing a boat. 

Reader Review
“Finding and buying a boat is a daunting task. There’s so much pressure to get the right boat for the right price. Emotions take hold and bad decisions can be made. With the ‘Viewing Boats to Buy’ guide my wife and I knew what to look for and why we were looking. After we saw a few boats we knew the one we wanted. We then got a survey and we’re extremely pleased with our decision.” John & Sally Keys
If all looks good there are two fundamental things to do:
Get a professional survey from a surveyor that does not know the broker, seller, marina and comes recommended by boat owners that have used him/her. And make sure there is a sea trial. You must see the boat working in the water.
Never, ever, ever buy a boat that has been on the hard where the owner is reluctant to put in the water to show that it works.
Chances are the boat doesn’t work or worse, the boat doesn’t even float. It’s imperative to find out if the engine works, the sails go up/out and the boat stays afloat. 
It’s also massively advantageous that you have specialists look at the large cost centers – the hull, engine(s), rigging and sails. Surveyors are not necessarily experts in all these areas… They might be great at spotting osmosis on the hull but terrible at determining if the engine is in a good state or not. Most surveyors will not go up the rig and hence you’ll have no idea if the rigging, a high expense item, needs to change. 
When we buy our next boat we’ll have an independent broker representing and working on our behalf. We’ll then have a recommended surveyor AND we’ll bring in a mechanic to fully investigate the engines. We’ll also have a rigger inspect the rig. 
There are probably more lemons out there than you’d expect. During this part of the process, it’s vital to do your homework and make sure you have experts to support you.
#5 Getting a boat with lots of storage.
This is the scenario we hear often. Hubby says ‘I really want to go sailing.’ And his wife replies, ‘Sure thing as long as I have loads of space to put things.’ The couple then goes to buy a boat that’s too big and load it down with too much stuff. Especially on Catamarans, the boat gets slower and slower the heavier the load.  
After a few months, the couple then offloads half of their stuff and has to give it away, sell it or ship it back to the mother country. 
My suggestion – start with the minimum amounts of everything. You only need a week’s worth of clothes, a couple of pots and pans, and a Kindle (not real books). You certainly don’t need anything of value – jewelry, keepsakes and so forth. 
If you’re planning on selling your house, see if you can borrow someone’s garage for a few months. Put all your stuff, that you think you need to keep, in the garage. I guarantee that when you return to look at your stuff you’ll think, ‘why did I keep any of this?’ And then you’ll finally offload everything. 
I’ve never met newcomers that have told me that they packed the boat with too little… It’s always way too much. 
And getting a boat that’s too big can be a liveaboard life breaker. We’ve met many that couldn’t handle the boat or were too scared to take it out because they actually needed more crew. Bigger is not necessarily better.  
When finding the ‘right’ boat it needs to be a boat that you and your partner/family can handle. 
Join us on Britican and find out how to make the lifestyle work as a couple and a family.
#6 Having a noncommittal partner.
We’ve seen an increase in newcomer boat couples, and families, where one person does all the boat work and the other(s) are passive passenger(s). Simon and I can barely keep our boat running with both of us doing all the boat jobs. We often have a third person to offer an extra pair of hands.
Trying to sail, maintain and service a boat while taking care of another person or family is not ‘living the dream’. It’s more like a nightmare. 
You can’t always helm the boat and also anchor or pick up a mooring ball. Especially in windy conditions, it can be extremely difficult to do these tasks with two people. You can’t helm the boat, fix a terrible leak and take down a sail all at the same time. Yes, there are solo sailors. But those solo sailors have the boat rigged in a certain way to make it possible to sail alone. Most standard boats are set up for at least two people to operate them. 
If you want to get out sailing but your partner is reluctant, I suggest you slowly get your partner into the boating life by doing a Charter. Show your partner the amazing lifestyle and highlight the massive benefits of being a liveaboard. Once your partner can see the incredible upside, then it’s time to get them interested in wanting to learn how to sail, take care of the boat and so forth.
This is going to sound harsh, but if your partner can’t operate the boat what happens if you fall overboard? Not only will he/she not be able to save you but they may not be able to save themselves.
Dragging your partner and/or family into the lifestyle without full support and assistance will not work. 
#7 Doing too much too quickly.
If you and whoever you’re planning on sailing with has experience on the boat you have, that’s great. And if you’ve done long passages in the areas you plan on going, that’s great too. If however, your sailing experience is on lakes and you are heading out into the Ocean, it’s not a good idea to plan a long first voyage.
The Atlantic is freaking nasty. I can’t tell you how many people go out on it once and vow never to return. Instead of planning a trip from Fort Lauderdale to the Bahamas (crossing the sometimes very turbulent Gulf Stream) it’s better to take the boat out for a few miles, practice anchoring, start to understand the weather/sea state and build up experience. 
I know we all want instant gratification but when you take a new-to-you boat out into the big ocean you’ll quickly realize that you’re not only in a harsh and volatile environment, but you’re all alone. You don’t want to be halfway to the Bahamas and have something major break when you’re starting out. You want to be close to land so you can call someone to tow you in!
Take the boat out over and over and over in an area close to home, land or a tow service way before a longer passage. 
Learn more about sailing AND the liveaboard lifestyle. Join us on Britican. Click the image for more info.
#8 Thinking the grass is greener.
This whole ‘living the dream,’ thing is quite a con. Once you start living the dream, life normalizes and life becomes very similar to the life you were living before you started living-the-dream. If you’re setting sail because you want more freedom, a closer connection to nature, the thrill of adventure, to find a community with similar values or to just get away from the rat race you’ll gain all those things. 
You’ll also gain boat problems, dealing with hurricanes, having to overcome seasickness, health issues in foreign substandard areas, feeling homesick/missing friends and family, being stuck somewhere for weeks and even months waiting for parts, getting fatigued by hot weather, mosquito bites, family mutiny and more. 
The grass is not greener. You can get everything you want where you are now. Make sure the grass you’re on now is awesome and then buy a boat and your life will truly be a dream come true. 
#9 Lack of education and lack of experience.
You need both education and experience to make the liveaboard lifestyle work. Many people focus on getting sailing skills but you actually sail very little in comparison to being at anchor, on a mooring or in a marina. 
Of course, you need to know how to sail, the rules of the road, passage planning, weather forecasting, and provision preparation but that’s just the tip of the iceberg. Furthermore, there’s the stuff they teach you to get qualifications and then there’s the way that everyone actually does it. For example, no one uses charts and dividers anymore. Apps take care of everything all on one screen. 
And while stationary, there are systems to maintain – the engine(s), water maker, refrigeration, plumbing and pumps, cleaning, deck and deck fittings/rig and on and on.
The best way to get education and experience is to get the best boat you can and take it out as much as possible – every day, every week, every weekend. By doing so you’ll learn what education you need and every trip, even a small trip, will provide you with an excellent learning experience. 
Or consider joining us or another liveaboard boat to gain education and experience from those that are living the life you’re transitioning into. See below.

Join us on Britican for a week-long liveaboard sailing experience. Each experience is created bespoke to you/your partners/your families needs. Learn how to sail at night, plan passages, and/or book into foreign countries AND enjoy the sun, sand and sea of the tropics. We teach singles, couples and families what it truly is like to live the liveaboard lifestyle. Let us help you to make your dreams come true! Click here for more information.
#10 Not preparing for a transition from a fast-paced career to the slower-paced sailing lifestyle. 
Many of the people we meet on the sea are ex-business owners, loads of pilots, engineers, doctors, lawyers and a whole slew of other professions. Going from a high-powered-I-am-someone position to a newcomer boat owner is not an easy one.
The key with this is to know that there’s a transition to be made. You’re not going to go from being a type A fast-paced worker to lazy gin drinking salty sea dog (not that that’s the aim!).
Many cruisers start a blog, offer consultancy (in their line of work) or figure out extra hobbies to take up while sailing. Some start to do woodworking, learn an instrument, join all the liveaboard social groups – playing dominos, cards, going golfing, etc.  Sure, sailing and maintaining the boat take up a lot of time but there is a lack of mind work or a creative outlet. 
If you’re going from high-power to the slower pace of a liveaboard life consider how you’ll make that transition easier. And give yourself time to acclimate. 
#11 Failing to appreciate the process of transition (giving up too soon). 
Some people decide they can’t hack the lifestyle within a few months. Gosh, it takes a long time to truly get into the groove. When we first started out a seasoned sailor told me that it took her and her husband three years to really get everything nailed down pat. I thought, ‘three years!’ I hate to admit it, but she was right. That doesn’t mean that the first three years were bad…they were amazingly awesome and incredibly difficult – now, after five years of living this life we’re more balanced. Simon knows what he’s going to cover and I know my roles. 
They say that it takes someone three years to really feel at home after moving house to another city/state. On a boat, you’re not only moving house but you truly are moving to a different lifestyle. There is a transition that has to happen there. The good news is that there are loads of people out there that have done it and are doing it. Online you’ll find loads of cruiser groups to support you through the transition.
Enjoy the Caribbean beaches AND learn how to be a liveaboard cruiser. Click here for more information.
#12 Unrealistic expectations.
Some people seem to think the liveaboard life is an escape. The just see the good side of things – the sun, sandy beaches, lobster dinners, inexpensive anchorages. Not yet have I met anyone who’s told me, ‘wow – this whole liveaboard lifestyle is way easier than ‘normal’ life.’ In fact, most people say, ‘I knew it was going to be hard but didn’t realize it was going to be this hard.’ 
I equate it to having a baby.
I kept telling everyone that I fully understood the responsibility of having a child yet when I had Sienna I thought, ‘Holy crap, I totally underestimated how hard this is!’ Interestingly, having Sienna was one of the best things I ever did. Similarly, moving onto our boat has been immensely rewarding. Perhaps there’s something to be said about us all wanting to be happy. Maybe it’s not happiness we really need? 
What should you expect? Expect to move to a world where things take forever to happen, everything costs 5x to 10x what you think it should, your home is constantly breaking, dissolving or wearing away AND at times it can be a bit scary (storms, hurricanes, taking on water, etc.). You should also expect amazing connections with new friends, views to make your eye’s smile wide and a sense of freedom and peace that simply doesn’t come easily back on land. 
#13 Failing to develop a healthy routine.
When you move aboard the boat and get out sailing it’s very easy to go into vacation mode and spend way too much money, drink far too many rum punches and become very unbalanced. Exercising is not easy on a boat and although you’re often surrounded by land it’s not as easy as you think to get to land and find a place to walk/run/exercise. And everyone says they’ll swim every day but that just never seems to happen.
Before you get on your boat, have a think about what habits will help you to be healthy. Write them down, post them on the wall and just make sure that every day you do what you need to maintain some sort of balance. Whether you need to meditate, take an hour to listen to music, eat certain foods or have a laughing session by looking at silly YouTube videos…make sure you fit these things into your routine. If you don’t, you’ll be forever fixing something on the boat. 
If you don’t put the rocks in place in your life, you get filled up with sand and there’s no place for the rocks to go. 
Try-before-you-buy the liveaboard lifestyle. Spend one week with us to give the life a test drive. Learn about sailing, anchoring, maneuvering in marina’s, docking, provisioning, cooking, maintaining, troubleshooting AND checking out all the white sandy beaches, snorkeling over the fish-filled reef and testing out exotic tropical drinks. You create the itinerary – if you want to try sailing at night, we’ll sail at night. If you want to gain confidence on passage planning, we’ll plan passages. Click here for more information.
#14 Not having enough financial support.
We’ve met quite a few liveaboards that are what you call, ‘winging it.’ They have a bit of money but are trying to make an income while living on the boat. Some people are comfortable with that arrangement. Others, like me, can’t stand the thought of running out of money. 
Many people sail for a while, return to land to make more money to get back out and sail again. Some people sail for six moths and work for the other six. There are loads of options but not having something that’s going to work can cause quite a bit of stress. 
Finding work in foreign countries is not easy and it’s frowned upon if you’re seen to be getting paid and the locals are not. This area of concern is not necessarily something to put on the ‘we’ll figure it out later list.’ Learning to sail, maintain a boat and acclimating to the liveaboard lifestyle is quite a big bite to chew. If you can sort out a way to ensure a monthly cash flow it will make the journey far easier. If you don’t already have my FREE guide about how to Make Money While Sailing Around the World, you can click the link to request it. 
#15 You Tell Me.
What’s missing? What else do newcomers to the liveaboard lifestyle need to know? Please leave your thoughts and comments below.

CREDITS: Currently on board with us is Chiara Magi, the lovely person taking the pictures you’ve enjoyed today. Chiara is an amazing person. She’s smart, beautiful, talented and eager to experience the world. She was born in Estonia but currently lives in Italy. Chiara is videographer so check her out on YouTube/Chiara – I wonder if Chiara will be bitten by the liveaboard life bug and consider a future life on the sea?

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