
Oftentimes we would be daydreaming about the ultimate freedom we’ll have once we retire. We’ve worked hard and now deserve to do exactly as we please. We’ve served everyone around us for far too long, our boss, our employees, our kids, our grand kids and everyone else that came in our paths. Now we’ve had enough and start planning retirement. We start watching fun channels on YouTube and run into so many sailing and cruising videos that we get hooked. We cannot wait to see the next destination, pristine beaches, palm trees, friendly locals – the idyllic way to spend the rest of our days. We’re going to sell everything, buy a boat, learn how to sail and off we go into the sunset.
This scenario is true for so many people. For some it works out fantastically, but unfortunately for others, it does not look anything like the YouTube channel! Cruising turns out to be just another way to live your life. Some folks are as happy as can be in a tent, an RV, their own home or anywhere else on the planet. Others seem never to find their ”happy place”. They’ve tried it all – camping, staying in fancy hotels and resorts, traveling the world by different means, are always in search of a new adventure and therefore cruising must be it, right? Well, for some it is and for some it is not. So, how will you know if the cruising lifestyle is something that you will enjoy after retirement? I have a few ideas to think about.
- Be realistic in your expectations
Happiness comes from within and if you’re not happy now, chances that cruising will make you happy is slim to none. Yes, it can improve your exterior situation i.e. no nagging boss, no traffic, less stress, less family issues, etc., but it remains life, simply in another place in another home that happens to float on the water.
Everything is not suddenly sunshine and roses. There’s still your everyday cleaning, cooking, washing up, laundry and so on. Sure, there’s no yard to keep and no pool to clean, but the boat’s bottom need as much (and more) attention as your yard, and yes, the pool is a bonus – not your responsibility to keep clean, just dip in whenever you feel like it and move on:-)
- Are you and your spouse completely compatible?
This seems like a strange question – after all, you’ve been married for 30, 40 or more years, so you should be fine. Living in very confined space for extended periods of time, under sometimes really stressful situations, puts a lot of stress on any relationship. In the past, when things got a bit scratchy, you could go for a walk, go to the other side of the house or yard, visit you friend, or whatever you felt like doing to just get a bit of “space”. On a boat that luxury does not exist. If you’re at anchor somewhere, either one can jump in the dinghy and go to shore for a bit, but while sailing, there is nowhere to go but to face each other and work it out. We’ve met a few couples that started out seemingly happy, and then when we meet up with them a few months later, they are divorced or have split up permanently. Being so close together can be absolutely wonderful or if not, absolutely miserable.
- Know your capabilities
Not all of us are mechanically inclined, handy men/women, do-it-yourselvers or great homemakers. If, until now you’ve hired everything out, the suggestion would be that you start taking an interest in how to fix things. It is a fact that something will break at a time where there is no one close to fix it and inevitably, it will be where you least want it to – like going through a dangerous inlet, past rocks with a strong current, or something similar. Nothing ever breaks in calm waters near shore where you can call a mechanic or friend to come over and help. It breaks in the middle of the night while a storm is raging and everything is flying around in the boat and everyone is hanging on for dear life.
Thousands of people have done it before, so yes, it is definitely possible to handle any situation that comes your way. Just prepare yourself as well as possible and learn as much as you can about all the systems on your boat. Take spares of everything and be sure to know how to use them – specifically in an emergency.
- Health and wellness
It sounds very obvious to take care of yourself and be sure to be in the best health possible before you set out to spend your retirement on a boat. Firstly, it is hard to believe how much physical work goes into sailing. Pulling on ropes, turning winches, balancing while the boat is moving and oftentimes also when at anchor, hanging on to rails and anything you can grab all takes a toll on your body. If you haven’t been on the boat for a while and then go back to sail for a few days, you are quite exhausted at the end of the day and muscles that you didn’t know exist, all of a sudden ache.
One of the first things to consider would be if you are on chronic medication, how will you get it if you’re offshore somewhere. Even if your doctor is willing to give you a prescription for a few months down the line, the country where you happen to be, will not necessarily be willing or able to fill it. There might be substitutes for what you’re using, but the pharmacist might not be willing to give it to you without your doctor’s consent. Off course, you don’t need to cruise outside of where you live, or you can even cruise for the period that your medicine is prescribed for, return back home and then carry on cruising again.
If you’re not physically fit, now is the time to start working on it. You definitely need some strength if you want to live on a boat. It is also a great idea to start working on your balance. The stronger you are and the better your balance is, the easier it will be to cope with boat life. Just getting in and out of the dinghy on a regular basis can be a challenge. And if you like snorkeling or diving and you do it off the dinghy, that can really become a challenge getting back into the dinghy from the water – even with a ladder in the water.
- Finances
Firstly, I am not giving financial advice of any sort. I am merely telling our story as it relates to finances. There is a cruising style for every conceivable budget. You can spend as much money as you have on the most luxurious yacht with crew, captain and chef and a helicopter landing pad on the upper deck and a luxury tender stowed in the lower deck, or you can cruise on a 22’ wooden raft, and anything in between. Our experience is currently on a 1978 Morgan OI, ketch rig, 41’ monohull sailing yacht.
The saying “sell everything and buy a boat and live free forever” is bantered around quite often and it is simply not the truth. We bought a very modest boat, tailored it to our needs, kept our rental properties for income, rented out our home and then went sailing without a plan of how long we would be gone for. Our first trip lasted 2 years on a 1963 Pearson Vanguard 33’ boat with no bells and only one whistle. We sold her in the USVI, flew back to the US to buy a bigger boat. We bought our current boat which had a lot of work to be done, started the process but then life got in the way and we had to put her in storage for a while. We wanted to experience the true cruising lifestyle before we “sold everything and move onto a boat”. We absolutely love the cruising lifestyle and everything about it, but we still have our land based home and rentals. We currently cruise for 4 – 6 months a year, but are planning a much longer trip for the next year/years.
I believe, and we are testimony to that, that you can enjoy your golden years cruising around on an older boat with a modest budget. We don’t need all the bells and whistles of the newest catamaran on the market. We have all the essentials (in our opinion) that we need – enough solar and wind power for our needs, a water maker, good communication and plenty of food and drinks. Where we are right now, we haven’t seen the inside of a shop for more than 6 weeks and we are not lacking a thing – this is what we call freedom.

A lot of questions are asked about how much it costs to live on a sailboat for a month. That question has as many answers as there are cruisers. Some of the variables are:
- Are you willing to anchor out most of the time, or do you want to stay in a marina
- Do you want to eat out regularly or do you eat on the boat
- Do you like to drink out or on the boat
- How much socializing do you intend on doing
- What is you medical needs and expenses
- Full insurance or only liability
- Where do you provision
- Do you fish and forage
- Subscriptions, magazines and other monthly expenses
- The list goes on….
The way you’re used to living your life on land will definitely have an influence on your budget on the boat. Everything doesn’t just magically change once you retire and go cruising. If you’re used to and love the more expensive lifestyle, your sailing budget will reflect the same.
- Family
A question that needs to be answered or thought about seriously concerns family, friends, church and other groups that you belong to.
Will you be flying back for birthdays, weddings, graduations, funerals, unexpected illness or other special occasions or are you willing to miss some important events?
One of the most serious mistakes you can make when cruising is to have an ETA. Many a sailor or cruiser has gotten into very serious trouble when trying to be at a certain place at a specific date and time. Wrong decisions are then made and not enough caution is heeded to weather or potential hazardous weather along the way.
- Is this something your partner and you completely agree upon
Is retiring on a sailboat only one partner’s dream while the other will just oblige and hope for the best? This would definitely be a situation where before you “sell everything and go cruising” you would try it out for a while first. Having a few days and nights in a row on uncomfortable seas and anchorages, can change oblige into resentment pretty quick.
The content of a lot of arguments on a boat is probably not the problem, whatever that current argument might be about, so much as the tension of living in a limited space with a limited income; when a boat that began as a dream of freedom becomes a form of imprisonment.
In conclusion, we had not considered that for a lot us of living in a very populated world, the sea is the last frontier. For the present at least, the great oceans of the world are still unpredictable, ungovernable, largely unrestricted, untaxable, unprotected by social legislation, impervious to 24/7 news media, untrammeled by lawyers and emotional trauma counselors or health and safety directives and not remotely political correct.
This is probably why a lot of people now dream about this ideal life of liberty, and if it works out for you, it is absolutely marvelous. Unfortunately, not everyone can handle this new life of liberty and would rather go back to safety.
Good luck with your decision and hope to see you somewhere on the oceans of the world!

Comments
2 responses to “Is cruising the right option for me after Retirement?”
All so very true, especially the physical requirement. Do you have any physical limitations, those can severely limit what you can deal with when sailing. Both of you have to really commit to the space limitations, love does not conquer all. Seemingly minor things on land can become a really bothersome issue when at sea. Standing watches when doing a crossing of large distances is something older couples must understand and be willing and able to do. Learning some new mechanical and navigation skills is also necessary, unless of course you plan on traveling from marina to marina, which is an ok option for those less adventurous
Hi Barry, thanks for your very valuable input! These are definitely issues that we have to consider and deal with. I agree that travelling from marina to marina is also an option for some and so is travelling on the ICW on a motorized yacht if you live on the East Coast of America.