How Does Someone So Young Live On a Sailboat?
It's about mindset and less about money
“How does someone so young live on a sailboat?”
This was the first question our veterinarian asked me when she barreled into the exam room. Our near-18-year-old cat, Pineapple, was getting her final vaccines that would allow her into the Bahamas.
The vet was a 60-something Southern woman who had a toughness about her that I knew could cut through anyone’s B.S. I’ve always appreciated talking with these sorts of women.
“Fair question,” I said. “We had some cash saved and decided to take a big risk that we could figure out how to make this work. Even at our age. Then, we decided we’d rather try it now while our bodies were in good shape.”
Then she got quiet, like she was reflecting a bit. She said, “You can always make more money later. Your mind & drive will last longer than your body.”
I nodded in total agreement.
Then she turned to the patient: our old boat cat, Pineapple.
“So she’s taking to the sailboat alright?”
“Very well!” I answered. “She’s loving her boat chapter.”
The vet said, “You’re modeling good behavior for her. Whatever you’re doing, keep doing it.”
She pinched Pineapple’s skin and injected her final vaccines. She told us to have fun in the Bahamas, then left the exam room.
Pineapple and I walked back to our dinghy and then headed to our floating home where my husband had been getting everything ready for our next sail south.
But I continued to think about the vet’s question.
How do we live on a sailboat?
The answer isn’t just about having savings and embracing risk. Lots of people have enough money but spend it in ways that don’t lead to a freer future. Other people gamble all the time — just by putting their money & time into things that don’t give them a great ROI.
To live a life that you design, you need something else: the ability to live boldly.
Luckily, this is something you can cultivate over time.
It sounds cliche to talk about deathbed regrets, but this is relevant here. According to Bronnie Ware, who writes about conversations she’s had with dying patients in palliative care:
“Most people had not honoured even a half of their dreams and had to die knowing that it was due to choices they had made, or not made.”
The answer?
Do it as soon as possible.
Do it even when you don’t feel ready.
Do it scared.
That means now, or in 1-5 years — not 30 years.
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We Forced the Life We Wanted Most
This week, we continued sailing south down the U.S. East Coast. I wrote some of this newsletter while we were 15 miles off the coast of South Carolina in the frigid Atlantic Ocean. We’re taking advantage of every possible weather window so we can make our big jump to the Bahamas.
In the Bahamas we’re looking to spearfish & snorkel, enjoy the beautiful beaches, and sail from one island to the next on a timeline of our choosing.
I’m going to stock up the boat one last time with provisions so we can save more cash and live off the grid as long as possible.
Pineapple is all vaccinated and, as an older kitty without much body fat, she’s also excited for warmer weather.
Five months into this journey, I’m still getting better at balancing our big goals with the practical steps to achieve our mission.
For example, much of this journey has been slower than I thought. I’ll think: Can’t we just sail straight to the Bahamas? We considered it! But the weather windows aren’t long enough for us given our skill level. So, we’re taking it jump by jump. We’re practicing patience.
We’re spending two or three nights at sea at a time, which has been absolutely magical.
I’m focusing on savoring every second that I get to live on the water. I realize how fortunate I am to have been able to break free and build a life on my terms.
But I also want to spend much more time working on the next part of this journey: showing you all that you can do this, too — if you want.
Look at me as a case study for what’s possible. I didn’t have a trust fund, nor did I have all the skills to be an ocean sailor. But I guarantee you: I’ll figure it out.
What choice do I have?
Right now, I have a bunch of ideas floating around on how I can continue this adventure indefinitely if we so choose. But lately, instead of fearing the unknown, I’m loving the mystery.
Objectively, we have less money in our savings than we did earlier this summer when I was freaking out about money. But I feel more serene today. How is this possible? Because I recognize that we have a boat full of food, we’re living the life we want, and we’re good for the immediate future.
This is proof that it’s all about our mindset & expectations.
The key is to not get too fixed to one version of our story. I’m learning to go with the flow and trust that I’ll figure it out.
We’re aiming to sail to the Eastern Caribbean and then Grenada by next hurricane season. But I’m not sure what will happen instead.
We may fall in love with the Bahamas and take our sweet time.
This year, the fees increased to enter the Bahamas on a sailboat. We’re paying nearly $1000 just for the privilege to sail, anchor, and fish in the country (including $150 for a permit for Pineapple). But instead of getting too down about it, this may lead us to savor it longer.
We could then find a hurricane hole in the Dominican Republic or head to Central America instead of the Eastern Caribbean. Who knows? I’m starting to understand that flexibility is the point of this adventurous life.
So, how does someone so young live on a sailboat?
By embracing spontaneity.
By loving the unknown.
By staying fiercely devoted to my sailing dream while also understanding that things will continue to change — including me.
We may be modeling great behavior for Pineapple by embracing an adventurous life at any age, but she’s also been teaching us the importance of enjoying the spectacular now.
Our Future is Uncertain By Design
For many people, there are specific times in life when they embrace being a beginner. The last free decision some people make is what to study or do after high school. Then they act like they need to stay on that track for the rest of their lives. But this isn’t how to find fulfillment.
I refuse to get stuck in thinking any decision should last forever.
When we set out in June, we were dead-set on sailing around the world.
But as we continue, we’re realizing this isn’t flexible enough. We always have the right to change our minds — including how we pursue our dreams. So, next summer we’re going to reevaluate everything based on what we’ve experienced so far. This is how we’ll ensure we’re doing all this for the right reasons.
I’ll need to ask myself the big question that led me to sailing in the first place: Am I even living the life I want?
For years, I had asked myself this question every 6 months for two reasons:
If I said Yes, I could feel more committed to whatever hardship I was experiencing in the moment (there’s always hardship).
If I said No, I could start brainstorming about what to do instead.
Now, 5 months into our sailing journey, I ask myself, “Am I even living the life I want?” and my answer is HELL YES.
I have no idea what the future will bring, but we’re making a mistake if we think that just because we made some choices in the past, that’s our destiny forever.
At this point, I assume that we won’t live on a sailboat forever. This is because achieving one dream allows room for another one to take root.
For me, this is another huge reason why we shouldn’t wait to start pursuing our dreams. If we live to be 80 or 90, we can live an unfathomably eventful life!
I’m proof that we can change our minds, grow, and learn new things — at any age.
I didn’t know a thing about how to sail when we decided to buy a sailboat in Spring 2024, and I barely knew how to sail on the day I quit my job and moved onto a sailboat in Summer 2025.
But I believe passionately in having a growth mindset.
This is how we can all achieve impossible things and change our worlds.
How We Rediscover Our Passions
Not everyone will want to change their life trajectory the way I have, and I totally get that. But this is much different than believing that it’s not possible.
Research has shown that we can all change and learn new skills. The idea that we need to stay stuck is so outdated. Don’t buy into that.
The biggest determinant of whether we will grow is whether we believe that our starting point is something we can build on through our efforts.
Then we need to get out our own way.
Many people will blame their responsibilities, like kids, debt, and other complexities of adult life. But they ignore the countless people who have had those responsibilities and still made radical decisions to change.
Thankfully, I knew of people who had started as novices and still managed to sail around the world.
But I also know of families living on sailboats — both on YouTube, blogs, and, now, personally.
The real question isn’t whether we can — it’s deciding what we want.
I talked to an old friend last week who told me he didn’t know his interests anymore. He feels a bit stuck in his job, but he also doesn’t know what else he would be doing — especially with a family.
“Why sailing? Out of everything you could’ve done, why’d you move onto a sailboat?”
This was a good question.
I explained that I came across sailing after I realized I wasn’t living the life I wanted. Then, I began to reflect on my values and discovered people who had explored some alternate path outside of the box.
Here is my process.
Questions I asked myself:
1. What values do I aspire to?
For me, it’s adventure, passion, freedom, authenticity, creativity. Living in the unknown. Building resilience.
2. Who’s living according to these values?
This is where I found frugal sailors like Sailor James. Once I found them, it became clear this is what I wanted.
3. What’s the practical path?
Relocate somewhere cheap with a good sailing community. Work remotely 10 more months. Refit a small sailboat ourselves. Follow the model of folks with less money, more focused on values.
We Deserve to Love Our Decisions
Not everyone will want to live on a sailboat. I don’t blame them. But everyone deserves to ask themselves: “Am I even living the life I want?”
If your answer is Yes — commit to it fully, even when it’s hard.
If your answer is No — start asking the three questions above. Find people living according to your values. Chart the practical path to get that life you want.
You don’t need to figure everything out before you start. You just need to start.
Question for you: What values do you hold most dearly? Who’s living according to those values? What’s one small change you could make to align better?
Feel free to DM me or leave a comment! I’d love to know.
Until next time,
—Cory Vinny
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I've never thought that I or anyone else has to follow a specific path. 24 years ago I decided I wanted to live on a sailboat. 10 years later it happened. There wasn't a lot of thought. It was just, let's do it. In three months we bought a boat, sold our stuff, rented the house, got the boat ready and sailed to the Bahamas. We were 48 and 52 then.
We had no idea what was next. We just followed the path as it appeared in front of us. We have sailed, traveled in a van, backpacked as senior citizens, house sat.
I'm sure it is scary for most people to take that first step. But once you do, you just follow it where ever it is heading.
Looking forward to reading more about your journey!
Cory — this whole piece is such a perfect snapshot of what full-time travel actually looks like. Not the dream — the doing. The cold Atlantic, the vet with zero B.S., Pineapple earning her sea legs, the reroutes, the mindset shifts, the money wobble, the “we’ll figure it out” energy. This is the real thing — choosing the life you want over and over again, even when it’s messy or slow or sideways.
And Pineapple modeling “good behavior”? I laughed — she’s basically the nautical cousin of Natalie’s grumbling pup Gryphon in the RV. Different roads, same wild spirit.
Natalie and I have been unpacking the behind-the-scenes side of all this in our “what full-time travel actually looks like” postcard if you want to compare notes:
https://thebenthalls.substack.com/p/two-roads-to-full-time-travel-postcard-what
As for your question — my core values come down to freedom, curiosity, and connection.
Nigel and I try to shape every decision around those three things.
One tiny shift that keeps me aligned? Saying yes to the next small step before I feel ready — and letting the rest catch up.
Give Pineapple a victorious head-boop from us — she’s clearly living her best chapter.
💛 Kelly