Mistakes to avoid when planning to retire on a sailboat.


While you’re still planning and dreaming about retiring on a sailboat, there are a lot of things to consider. There’s also a lot of information available on the internet.  Most of the information is aimed at much younger people and some of it would only make sense if you’re fresh out of school and haven’t had a place of your own yet.

There are definitely a different set of rules when you’re planning retirement and also want to do it on a budget. My advice as always is not to sell everything and buy a boat, but rather to test it out first. Off course that can be expensive if you buy a boat and then find out that either partner doesn’t like it as much as they thought they would, or become sick or disabled before the journey can even start.

There are opportunities to check out different kinds of sailing vessels for a week or more to experience a little bit of how the cruising life is in real life.

By reading this article, you will be on the lookout for some common mistakes that many sailors have made before you and can then avoid making them also.

  1. Buying A Boat Without any experience

If you have no experience with sailboats, it potentially is the best way to throw away thousands of dollars if you jump in and buy the biggest and best boat that you can afford! If you are not familiar with what sailing a boat is actually like then you’ll have no idea if you want to spend a day on a boat, let alone live on one. Many people move onto a boat thinking it will be like living in a small house when the reality is that it is completely different.

You need to be prepared for the constant motion, the fact that you need to make do with much less than what you’re used to, your belongings need to be stowed away at all times, very limited storage, etc.

If you think you want to live aboard then one of the best things you can do is to get onto a boat and spend at least a full week on it either sailing or at anchor, preferable both.

2. Moving Aboard Without a Financial Plan

When planning to retire on a sailboat, the assumption would be that you have considered the financial implications and are prepared for what lies ahead. However, while we are discussing retirement on a sailboat on a budget, we need to understand that things can come up that we never thought would become an issue.

It’s easy to read the success stories of others and think that making money to supplement your savings or retirement benefits will be easy when living on a boat. One of the biggest mistakes is to think that it is free to live on a boat. It can potentially be cheaper in the sense that there are no property taxes, no need for a car, no utilities to pay, etc. However there are many other things to consider that may be much more expensive than you thought, like boat maintenance, marina fees, fuel, solar and batteries. It is important to be realistic about monthly costs on a boat. We’ve seen lots of cruisers run out of savings before the real adventure has started and then have to give up their dream and go back to living on land.

The best is to have a plan before you set out. Make sure that you understand how much maintenance and other unforeseen expenses can run into and budget accordingly. Again, there are lots of sites that suggest that there are many different ways to make money while sailing, but in my opinion it is not feasible for retirees.

If you have a job that you can keep on doing while cruising, that will definitely be feasible, but some of the other options like cleaning bottoms, doing repairs on other boats and other services do not normally fit in with retirement. Don’t rely on making money from becoming a YouTube sailing channel, or making it big on Instagram.

Very few people manage this, and even when they do it isn’t a reliable form of income. Think more long term and you’ll be sorted for as long as you need the adventure to last.

3. Not setting up the boat properly before setting sail

People of all ages have lived on all sizes of boats for many decades and some have even crossed oceans in anything from rafts, paddleboards and rowboats to any size modern sailing vessel.

It is definitely true that you can go sailing with very little, but making your life easier with some comforts that you enjoy on land, like having enough energy to run your freezer and refrigerator without stress, having enough fresh water and not having to dinghy water to the boat or constantly being on the lookout for marinas to fill your water tanks, etc will make a huge difference to how long you can enjoy the cruising lifestyle for.

Electronics, technology and communications are of utmost importance if you want the lifestyle to work out. You need internet to check the weather, which will become the most important daily task, regular communication with family and friends also makes the lifestyle easier, and with modern technology you can call anytime, do your banking and in general stay on top of what is going on in the rest of the world with the luxury of switching on and off whenever it suits you.

Another very important aspect of your new boat is the ground tackle. In general cruisers spend about ninety percent of the time at anchor and therefore your anchor and anchor chain and/or anchor rode must fit your boat size and weight and also the bottom in which you anchor. Some anchors are better suited for sand while others do better in mud, so your sailing area will determine what your main anchor on the boat will be.  We always carry two anchors plus one or two spare ones on our boat plus a small anchor for the dinghy.

Your lifestyle will determine what upgrades you will consider doing first.
Think carefully about essentials before you head off into the unknown. These are some essential upgrades to consider.

  1. A good quality dinghy and outboard motor

This will be you “car” and will carry you to and from shore when you anchor out, go to explore and be used in an emergency.

b. A sufficient battery storage and charging setup

Calculate how many amp hours you will be using on a daily basis i.e. refrigeration, water maker, electric toilet (or head), fans, lights, etc and then purchase solar panels and/or wind generator accordingly. Secondly, you have to consider where to store the energy that you’re generating, so that will be your battery bank. Normally boats have two battery storage setups, one for house purposes (refrigeration, lighting, navigation, communication, etc.) and one dedicated to the starter on your engine.

Lithium Iron Phosphate batteries (LiFePO4) are the way of the future, and they have literally changed our lives on board! 

c. An anchor and ground tackle setup to cover your needs in various anchoring scenarios.

Your ground tackle, i.e anchor, anchor chain, anchor rode and so on, is extremely important since it is true that most cruisers spend more time trying to keep the boat in one place that what they do moving it.

Off course, if you plan on spending the majority of your time in marinas then your mooring setup will be more important like a huge amount of good quality fenders and hefty dock lines, but keeping the boat stationary is definitely something you should give serious attention to.

d. Invest in a water maker (desalinator)

This is a fairly large investment, but in my opinion, one of the almost necessities on a cruising boat. If you rely on the amount of water that you can carry, you limit the time that you can be away from the dock or how often you have to go to shore. Your living off the grid is thus severely compromised.

Carrying water to the boat in jerry cans from land is definitely not fun. The jugs are heavy, the quality of the water is not always above suspicion and in most cases you have to purchase water. That can become expensive if you think drinking, cooking, showering, doing dishes, some hand washing of laundry and so on.

4. Assuming that taking a Sailing Course is all you need

I do suggest that you take any and all courses you think that you may need for your new life on the ocean. We are talking about your partner as well as your life here after all! The only caveat here would be that real life on the ocean is very different from a classroom, video or YouTube can really prepare you for.

After you feel confident that you know all you need to know before buying a boat or moving onto your boat, it is still advisable to get on a cruising sailboat for a week or two to experience the constant motion, waiting for weather, sitting out unexpected storms, how and where to anchor, living in a very confined space, living close to your partner, getting on and off a dinghy and so many other aspects of real life sailing in retirement.

Provisioning, water conservation and cooking or preparing meals on a boat are not often covered in sailing courses. With this in mind, be aware of the fact that you’ll need to keep on learning when you move aboard. Ask the sailing community questions, watch other people and read up on the things you’re lacking knowledge in. The worst thing you can do is approach this lifestyle thinking you know it all or that it is similar to living in a small house on land.

5. Believing that you will have total freedom

Freedom is oftentimes associated with cruising and living aboard a sailboat. The reality is that this is not entirely true.

You will definitely have more freedom in certain areas but the weather probably is the biggest influence on your total freedom. Predominant wind patterns or trade winds will have a definite say over where and when you can go. In addition, the local weather patterns also have a great influence not only on where and when you can go, but also in your comfort levels if you stay.

You will find there are more times than you’d probably like when you can’t get off the boat, for various reasons. Oftentimes, we were anchored next to a beautiful-looking town or an inviting island, but we can’t safely get off the boat to explore because the wind is howling and the waves in the anchorage are just too high to make it safely to land and back. Especially when we’re a bit older, we need to take extra care when getting on and off the dinghy. This year was an extraordinary year with much higher winds than we’re used to, so we were literally “trapped” on the boat on several occasions.

You will also have to make tricky decisions over leaving the boat or not. We once wanted to fly home for our son’s wedding, but just the week before a hurricane blew through the islands and there was no way to get to an airport except to take the mailboat and share the passage with all kinds of cargo as well as a variety of live stock. We were fortunate that we had the boat in a small creek where friends of ours could keep an eye on it while we were away.

Sometimes you will be faced with the choice of leaving the boat in a marina at a very high cost or haul it out of the water and put it in storage if you want to take a break from the live-aboard lifestyle. Other times you will find that the winds are not favorable to sail to where you can get on a flight and then miss important family events.

Oftentimes friends and family get invited to visit on the boat on some idyllic destination without carefully planning and understanding that even with the best intentions, it will not always be possible to be at the airport when you said you will be there. Mechanical issues or unexpected weather can make it impossible to get to where you intended to pick up your guests. The same applies to getting your guests back in time to catch a flight. So, in our opinion, it works best to already be where you need to pick up your guests before they purchase their flight tickets, and then to make sure that there is an alternative way to get them back to the airport if, for any reason, you are not able to sail them back.

New live-aboards are often unprepared for this lack of freedom and for their lives to be dictated by mother nature!

6. Not being prepared to fix things yourself

A major mistake new live-aboard sailors make is not learning any boat maintenance.

If you want to live onboard a sailboat then there is no getting away from the fact that you’ll need to be handy (or at least prepared to learn!) If you have the money to throw at experts, then great, you might have to do less boat work, but you’ll quickly find out that things don’t choose convenient places to break!

If you’re a new live-aboard then we thoroughly recommend picking up a few basic maintenance books in areas you aren’t confident in. YouTube is great, but unfortunately it is very likely that your engine will develop a problem when you don’t have access to the internet!

Here are the kinds of books that you should be looking for:

Boat owners mechanical handbook

Marine diesel engines

Boat owners electrical handbook

Inspecting the aging sailboat

Also, make sure you keep copies of any manuals that came with the systems on board your boat too.

7. Declaring an ambitious sailing plan

It is totally fine to have any dream or plan you can think up, but first, take baby steps and build your experience, knowledge and confidence before setting out or announcing it to the world.

Many people move onto a boat and find sailing and especially long-term cruising, just isn’t for them, and there’s nothing wrong with that. Of course it will be very helpful if you find that out before buying you dream retirement sailboat.

Take the pressure off live-aboard life by testing the water first. How’s a month in a marina? Do you like doing overnight trips? Do you enjoy sailing overnight in areas you’re not familiar with? Have you spent a week or two on a sailboat? Remember, coastal day sailing in perfect weather conditions is vastly different from what the cruising lifestyle presents.

8. Thinking that moving aboard will change your life

The reality is that you’ll still be good old you!

Of course, aspects of your life will change when you move aboard, but ultimately you will still be the same person, with the same brilliantly complex thoughts and feelings.

Just because you’re now living your dream, or because you’ve moved halfway across the world, sailing isn’t going to change your life in the way you possibly hoped.

Remember, you aren’t changing your life, you’re simply moving it to a different home that happens to float on water. Don’t feel disheartened when sailboat life becomes boring and mundane, or when you have to spend the day doing admin, or when you simply feel grumpy and you don’t even know why. You’ll still get the highs, but sailing life won’t erase the lows.

Go into new live-aboard life expecting sunshine and cocktails 24/7 and you’ll be sorely disappointed. But go in remembering this is all part of your life’s rich tapestry and you’ll have an expectation much closer to reality – with all the incredible, the terrible, and the long boring stretches in between!

9. Not understanding local weather patterns

Get to know the weather in your sailing area!

Weather forecasts and charts are great – to a point. When we first started sailing we put all our trust in the wind forecasts and were frustrated time and time again when we ended up sailing in completely different conditions than what was predicted.

As new live-aboards get used to learning weather patterns that are specific to the countries and even areas that you’re sailing. Local fishermen are great sources of information, and you can get a good idea that something nasty is brewing when you see marinas and safe anchorages filling up with fishing boats!

Areas often have predominant wind patterns. Mountains cause all sorts of crazy winds to occur by either blocking them completely or creating katabatics, lees and land effect.

You can eat your lunch in a millpond and motor around to the neighboring anchorage to find 30 knots of wind and high seas. Shallow waters create different wave patterns and certain stretches of sea experience huge tidal currents. Study your sailing areas properly in advance to avoid nasty and sometimes very costly surprises.

When you’re starting out as a live-aboard (and beyond!) do proper research before sailing in new territories. Speak to as many people as you can, study charts and almanacs, and ask questions on sailing forums. You should also make sure you download all the best apps for sailing.

You can never know too much!

10. Buying a boat that is not suitable for your needs

Get the right boat FOR YOU!

One of the biggest mistakes new live-aboard sailors make is to buy a boat that isn’t suitable for their needs. Often this means buying a boat that is too big and therefore much harder to sail and much more expensive to maintain.

We had a great piece of advice before buying our boat – get the smallest boat you can cope with living on.

We have, however, seen cruisers go the other way and buy a boat that is far too small for their needs as live-aboards. Buy a boat that you can imagine spending a great deal of your golden years on!

It should be big enough to house you comfortably (though obviously a little cramped, this isn’t a country mansion!), but small enough for you and your crew to handle and maintain.

You should also make sure you buy a boat that’s suitable for whatever sailing you have planned. Don’t buy a quick, light boat for breaking ice up north! If you want to cross an ocean then make sure you buy a boat you will feel safe in.

11. Being scared to admit mistakes

Follow your gut!

The sailing community LOVES to share their extremely polarized opinions with new live-aboard sailors. While this can be incredibly helpful and is almost always imparted with the very best of intentions, it can get overwhelmingly confusing.

We will often go to research a topic only to find there are two completely different views, both of which seem to have very valid arguments.

The only solution here is to follow your instincts. Chances are both solutions will work

fine, but choose which one feels right for you, your crew, and your boat. Don’t be swayed by the loudest voice in the crowd.

Don’t be afraid of looking ‘stupid’.

If you enter a marina that is a little too crowded for your liking then leave and anchor out. If you set off on a passage and you don’t like the look of the conditions (even if the forecast predicts a great day of sailing!) then don’t be afraid to turn back.

The times when we say ‘this doesn’t look right’ but do it anyway because we feel pressured or the information we have says all should be fine are often the times when disasters happen.

The more experience you gain, the easier it becomes to NOT follow all the plans you made but to adjust as necessary for specific situations and conditions.

In conclusion, sailing or cruising when you’re young and full of life definitely looks different from when you’ve lived the best part of your life already. It is off course possible and surely extremely rewarding and pleasurable no matter your age. Being older myself and having many friends in their later sailing lives, made me realize that most of the information available on the internet and on sailing channels are fantastic for younger sailors but the expectations created do not always work for more mature adults. We simply do not have the strength, agility and balance that these young people have. If you are realistic about your capabilities, you can have as much fun as you can think up, albeit at a different pace as the younger generation. So, don’t be pressurized to do anything at anybody else’s pace – this if YOUR retirement and YOUR time!

Enjoy the journey and hoping to see you on the ocean some day soon!

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