Live aboard sailing | 8 ways to avoid failure

Some people take to live aboard sailing effortlessly. Others find it a struggle. Many discover that full time sailboat cruising is challenging and stressful yet enlivening and fulfilling.

But how do you know where you will fit in?

When your dream becomes a reality will you love it or is there a slight possibility that your dream could turn into a nightmare?

Over the past several years I’ve had the opportunity to meet hundreds of full time live aboard cruisers. I’ve met sailors of all ages that absolutely love the sailing lifestyle and would never give it up. I’ve also met several boat owners that can’t sell their boat, and head back to land, fast enough.

And I’m talking about full time sailing cruisers here – people that purchased a boat to actively sail it around; not people that are full time live aboards that never leave a marina.

First I’ll list the eight ways to avoid failure and then I’ll expand on each of them below…(keep reading)

Live Aboard Sailing

Live aboard sailing – 8 ways to avoid failure

  1. Gain experience. Sail as much as possible on other people’s boats to try before you buy (Charter, join a sailing club, take classes, etc.). Find out what you like, don’t like and whether or not everyone in your future crew really likes the sailing lifestyle – warts and all.
  2. Build confidence. Become confident with boat handling skills! Buy or rent a small boat to play with and allow yourself to crash and make mistakes. Get yourself to the point where you’re not afraid to handle a boat.
  3. Set expectations. Set accurate expectations. If you own a boat you’ll need to either have an unlimited amount of money for tradespeople to fix your issues OR you’ll need to get good at wearing the following hats: plumber, electrician, carpenter, heating/cooling expert, sail mender, mechanic, and on and on the list goes.
  4. Understand that problems are an everyday occurrence. Embrace the lifestyle of problem solving. Problems don’t have to be good or bad…if you want to live on a boat they are a part of everyday life. If you’re looking for a problem free lifestyle, being a live aboard cruiser is the wrong lifestyle for you.
  5. Generate on-going income. Make sure to set up income streams or have a plan that will enable you to pay for the lifestyle. Sure anchoring is free, but keeping the thing attached to the anchor floating has an ongoing cost.
  6. Understand the true nature of going with the FLOW. Learn how to go with the flow. If you’re currently a control freak, find ways to change. (It’s possible. I’m a recovering control freak).
  7. Prepare for hard work. Realize that being a live aboard cruiser is hard work.
  8. Have a future plan. Consider your future. Have some sort of plan. Mitigate the chances of getting yourself stuck.

Let’s dip further into these failure areas:

1. Gain experience

If you’ve never sailed before, don’t go buy a boat. If you have sailed before but haven’t completed a long journey (say…sailing non-stop over five days) don’t buy a boat. If you have sailing experience and have endured storms, bad swells, engine breakdowns, etc. but your partner hasn’t, don’t buy a boat.

Sailing into the sunset has many positives. For me, I can’t imagine living any other way. However, it is not something to jump into without prior experience. For every romantic notion you might have about the live aboard lifestyle there is an opposite.

Find a way to determine if you can handle seasickness, bad weather and all the other negative aspects to sailing. If you’re okay with those AND so is you’re partner (or other crewmember(s)), then it’s time to consider buying a boat.

2. Build confidence

If you go to almost any marina on a hot summers day you’ll notice that the vast majority of boats are docked rather than out at sea. Most boat owners are too afraid to motor in and out of a marina. Many newbie sailors get a boat and have a minor crash or two (totally normal!). Unfortunately, fear of failure stops dreams, especially sailing dreams.

If you’re going to buy a boat and want to enjoy full time sailing, make sure you can handle the boat you want to buy. OR ensure that you can live through failure, and the fear of failure, during the learning process. When we got our first boat we sailed through the winter when the waterways and marinas were less populated. It reduced our anxiety and increased our ability to manage the boat.

Even now we still get into tricky situations but our failures don’t prevent us from moving forward.

3. Set expectations

Sailboats need constant servicing and maintenance. Furthermore, there’s always a list of needed repairs. Boats live in the most corrosive environment on Earth. They’re surrounded by salt water and soaked by UV rays from the sun. Furthermore, boats are tossed all over the place making breaks and bruises a norm.

If you think that the live aboard cruising lifestyle is more about sunsets and sailing and less about maintenance, I suggest you think again.

There’s a balance between the two… For months we’ll go with only routine maintenance enjoying sailing and the positives to being a live aboard. We then might spend a month or six weeks fixing things. Sometimes a week will pass without major issues and sometimes months. Often, things break, we fix them and then something else breaks.

4. Understand problems are an everyday occurrence

When my husband and I are on the move, which can be for months, we often spend more time sailing and less time fixing things. When we’re stationary, however, we wake up every morning and discuss our list of priorities.

Which leak is the worst? What problem, if not solved soon, will lead to a more expensive problem? And it’s not just boat challenges. Often, when going to a marina the electricity hook-up doesn’t match the adapter we have OR we need a certain part but they don’t make the part anymore. Or, when we’re sailing, the wind is coming from the completely wrong direction as forecasted – we’ll never make our destination…what do we do now?

At first, I thought that eventually the problems would subside, but now I’m convinced that they actually increase over time. The more you learn about what you didn’t know, the more you realize just how many issues you really do have. Eventually I made peace with problems. Now it’s just a part of our life. Like I mentioned above, t’s not good or bad – it is what it is. Some live aboards can’t make peace.

5. Generating ongoing income

We’ve discovered that the longer we sail, the less expensive things get. We’ve grown wiser over the years. We know what is a con versus what is necessary. Furthermore, we’ve started to understand what has to be ‘marine’ quality versus what can be purchased at a normal store. We’ve also learned how to become more proactive so that we fix or service things before they break down.

Overall, however, boats require a constant stream of money to pay for the upkeep. Boaters that head out to the sea with a pot of savings will watch that pot evaporate. Without money, the live aboard lifestyle can become very uncomfortable. If creating income while sailing is a part of your future plans, make sure to read my free guide: ‘Making money while sailing around the world,’

6. Understand the true nature of going with the FLOW

Sailing and the live board lifestyle truly is one where things change all the time. More often than not, we’ll head from destination A to destination B only to end up somewhere near H. Several times we’ve wanted to leave an anchorage or marina only to have the weather or a repair stop us for weeks and even months! Being a live aboard cruiser you have to often make the best of the current situation…and the current situation might not be ideal. Live aboards that have a hard time going with the flow will find this lifestyle a nightmare.

7. Prepare for hard work

There’s a huge movement going on right now. Many people want to find a way back to a simpler life. A life, perhaps, without mainstream media and negative news or overwhelming amounts of stimulus. Becoming a live aboard sailor can help people to remove themselves from the mainstream rat race of go, go, go with every moment being measured in terms of productivity.

However, living a lifestyle on a boat is anything but easy or simple. Problems happen all the time. Getting and preparing food is often a challenge. And even the most basic things, that you probably take for granted now, become obstacles. Moving onto a boat definitely does not simplify life. If anything, it creates different stresses and issues. Personally, I prefer live aboard stresses over business world stresses…but needless to say, stress is still present and life is not easier.

8. Have a future plan

It’s no fun when you feel stuck. Some live aboards sell everything to get the boat and when things don’t work out, they have nowhere to go. If money is tied up in the boat, a situation can arise where live aboards have to wait to sell their boat before they can move on with their life. Some boats don’t sell very quickly…


So, what did we do to reduce our likelihood for failure?

How did we prepare for a full time live aboard sailing lifestyle?

For ten years, my husband, Simon, and I went on an annual week long Flotilla Sailing Holiday (boat charter). We often dreamed about buying a boat but never took our dream too seriously. We always thought – ‘one day’! After having our daughter, Sienna, we opted for a land based vacation rather than a sailing charter. We thought it wouldn’t be safe enough to take a six month baby on a boat.

Our vacation on land was miserable – we hated it!

Out of anger and frustration we decided the time had come to buy a boat. A month after our land-based vacation, we aquired a 35′ Moody sailboat. Simon found the boat on Ebay and we got it for a very low price. It was an old boat…but we felt that it would give us confidence and allow us to prepare for our dream boat ‘one day’!

Low and behold, we discovered that we loved sailing our Moody. We went out every weekend and took week-long breaks as often as we could. Every time we returned to the marina we’d be sad. For over a year we practiced entering and exiting various marinas. We endured an experience where we had engine failure in an extremely busy waterway. We also almost sank due to a snapped off through-hull fitting. (The list goes on…)

Needless to say, the more we sailed, the more we loved sailing.

Our original plan was to sell our house and buy another one closer to the coast. We wanted to sail as often as possible! One thing led to another and we decided, ‘heck, let’s sell the house, buy a boat and sail around the world!’ There was no doubt in our minds on whether we liked sailing or not. And due to sailing our Moody, we built up a good amount of boat handling skills over two years.

Before we left land we took a variety of live aboard sailing courses and had reasonable expectations. I think we thought it would be easier than it has been. Furthermore, it took me a very long time to learn how to go with the flow. I struggled for the first year to simply ‘let go’ of having to control things. Sailing taught me so much about that.

Regarding the money side of things, we have a variety of income streams, all described in my free guide, ‘Making money while sailing around the world.’

So…if you’re interested in becoming a live aboard sailor, make sure that some of these reasons for failure are addressed. And if you have something you’d like to add, please add it below in the comments section.