Setting Sail into Retirement

Retirement is a time to embark on new adventures, explore uncharted waters, and make the most of the freedom that comes with it. That’s why setting sail into retirement works. Keep reading.

While many envision their golden years as a time of relaxation and leisure, an exhilarating option often goes unconsidered – the sailing cruiser lifestyle. Whether you’ve never sailed before or are a seasoned sailor, retiring to the open sea can be an incredibly rewarding and fulfilling experience.

In this article, I aim to inspire those nearing retirement to embark on a new and exciting journey.  Let me debunk common misconceptions and shed light on the many benefits of the sailing cruiser lifestyle.

The 1st Best Time to Start Sailing was 20 Years Ago, and the 2nd Best is NOW.

Before diving into the article, however, let me add a bit of my behind-the-scenes life. For the past year, I’ve been living with my mom. She had heart surgery and lost her husband. Our daughter, Sienna, wanted to leave our boat, go to a ‘normal’ school, and have a ‘normal’ life. So, long story short, I’m on land helping Mom and enabling Sienna to be ‘normal.’ This is after living full-time on our boat for ten years.

Then, my dad reappeared in our lives. So, I’m a 50-year-old who lives with her parents. My husband, Simon, is still doing Sailing Lifestyle Experiences, but when he’s not doing those, he’s with me, and we both live with Mom and Dad. The plan is to sell our boat and buy a house. Let’s get back to my parents…

Lessons on Aging

My first comment is that it’s been wonderful living with Mom and Dad. I’ve had a brilliant time getting to know my parents again. We have a blast. My second comment is that it’s been very enlightening as to what happens when you mature IF YOU DON’T PREPARE FOR OLDER AGE.

Mom and Dad are not in bad health. But they’re not great either. Neither of them exercises much. They don’t eat very well. And…their glass can often be far lower than it could be. What freaks me out is that I’m only 20 years behind them.

I’ve been watching my parents complain about aches and pains, take medications, and tell me that getting old is no fun. They have caused me to search out information about longevity and how to live a QUALITY life into older age. Ideally, I want to be running around living my best life and then suddenly die rather than slowly deteriorating and declining until I’m left in bed, unable to move.

Lessons on Longevity

So…I’ve read several books, watched the Netflix series Blue Zones (about the longest-living healthy people), and listened to podcasts about advancements in medical science.

My take-aways: Exercise. Eat mostly unprocessed foods, and reduce foods from SAD (Standard American Diet). Have a community of people around you so you feel a part of something other than yourself. Drink a glass of wine or eat the cake, but make sure you love every moment of it (rather than feeling guilty), and feed your mind! (Did you know they’ve discovered Alzheimer’s is preventable?!)

Regarding exercise, the key is to think about what you want to do at 90 and train for it now. If you want to pick up your great-grandbabies, do exercises that will enable you to do that. If you want to get off the floor after a minor slip, practice getting off the floor now. I could go on and on, but you get the point. Old age doesn’t have to be a slipery slope to doom. It can be something that you prepare for, embrace, and manage on your terms.

So, this is why setting sail into retirement might be the best plan for longevity for those who feel a pull for the sailing life.

Setting Sail into Retirement – You’re Never Too Old to Sail

One of the most prevalent myths about sailing is that it’s only for the young and physically fit. Sailing is a versatile hobby that can be enjoyed at any age. The very first sailing cruisers we met were in their mid-70s! With proper training and safety precautions, seniors can confidently take to the water and experience the thrill of cruising. Sailing not only keeps you physically active. But it also stimulates the mind, offering a unique combination of exercise and mental stimulation.

It’s an activity that can be as leisurely or as adventurous as you desire.

No Prior Sailing Experience Required

Another common misconception is that you need extensive sailing experience to live the cruiser lifestyle. While experience can certainly be an asset, it’s not a prerequisite. Numerous sailing schools and courses cater to beginners, providing comprehensive instruction on sailing techniques, navigation, and safety. Many retirees have successfully transitioned into sailors, learning the ropes (quite literally) and navigating the seas with ease.

Over the past five years, my husband and I have had many guests on our Sailing Lifestyle Experiences. Over half of our guests were 65 or older and had no issues. Sailing a bluewater cruising boat is manageable! You need to get experience, but setting sail into retirement isn’t difficult.

Setting Sail into Retirement – Freedom to Explore

The sailing cruiser lifestyle offers retirees the freedom to explore the world in a way few other lifestyles can match. Imagine waking up to the boat’s gentle rocking, surrounded by crystal-clear waters and breathtaking coastal landscapes. With a sailboat as your home, you can journey to remote islands and hidden coves. You can also check out vibrant ports while enjoying the comforts of your floating sanctuary. It’s a lifestyle that encourages spontaneity and adventure.

And the sailing lifestyle is not non-stop voyaging. For six months of the year, sailing cruisers take a break and hang out in one spot. In the Mediterranean, the ‘winter’ season is from November to May-ish, when cruisers find a marina to settle in. In the Caribbean, cruisers stop sailing during Hurricane Season (June to November). Other parts of the world are similar – cruisers hunker down for a while when it gets too cold or too stormy.

During the downtime, cruisers explore on land and take breaks to go home to visit family or simply sit and chill. The cruiser communities during winter or hurricane season are wonderful.

When we started, I loved exploring and moving, but after several months, I got tired. We then stayed in Sicily for six months, and it was AMAZING. We met many friends, visited ancient sights, and flew home to visit family. The sailing life provides this amazing balance of movement versus non-movement (I couldn’t think of a better word!).

A Strong Sense of Community

Setting sail into retirement doesn’t mean isolating yourself from society. On the contrary, sailing communities are tight-knit and welcoming, and you’ll find fellow sailors of all ages and backgrounds who share your passion for the sea. The camaraderie among cruisers is unparalleled, with opportunities for socializing, sharing experiences, and forming lasting friendships in every port.

And this is while you’re sailing and when you’re hunkered down for five to six months. Many people worry that they won’t have a social life because they’re tucked away in their boat from civilization. They couldn’t be more wrong. The social community in the cruiser world can be too much but never too little!

Setting Sail into Retirement – Simplified Living

Downsizing and simplifying your life is often a goal in retirement. Living on a sailboat encourages exactly that. With limited space, you’ll naturally declutter and focus on what truly matters. You’ll become more attuned to the rhythms of nature and the essentials of life, savoring every moment of your journey.

I mean, come on. Doesn’t setting sail into retirement sound perfect?


Retirement is a time to chase dreams, and the sailing cruiser lifestyle offers a unique and fulfilling path for those willing to take the plunge. Age should never be a barrier to discovering the joys of sailing, and lack of experience can be easily overcome with determination and training.

The sailing cruiser lifestyle beckons with the promise of adventure, freedom, and a sense of community that’s hard to find elsewhere. So, why not make your sailing dream come true in retirement? Set sail into this new chapter of life, and let the wind carry you toward the endless horizons of possibility. Your retirement can be a remarkable voyage filled with memories that will last a lifetime.

Join Simon on a Sailing Lifestyle Experience

Aside from learning how to sail, or improving your skills, a sailing lifestyle experience can offer much more!

Embarking on a sailing lifestyle experience as a couple approaching retirement can be a transformative and enriching choice. Sailing offers a unique opportunity to reconnect with one another and with nature in a way that few other experiences can match. It allows you to escape the hustle and bustle of daily life, trading it for the tranquility of the open water, where you can create lasting memories together.

Sailing fosters teamwork and communication, as you navigate the challenges of the sea together, strengthening your bond and deepening your understanding of one another. It also offers the chance to explore new destinations, immerse yourselves in different cultures, and savor the freedom of living at sea.

And an experience might just lead to a new lifestyle offering relaxation, adventure, and a shared sense of accomplishment. It’s a chance to sail off into the sunset and start a new chapter of your lives together.

Setting sail into retirement can start with a Sailing Lifestyle Experience. Book your Experience now!

Other Articles and Videos

Any Questions or Comments about Setting Sail into Retirement?

Please leave them below.

Kim Brown:
Related Post

This website uses cookies.