Living on a sailboat in St. Maarten During Hurricane Season

This blog explains why we’re Staying in St. Maarten during hurricane season in the Caribbean, while Everyone Else Is Leaving. A personal update on hurricane season, career pivots, and building something real.

St. Maarten is emptying out. Take Tony, where his boat was anchored before there is now an empty spot. He weighed anchor and sailed off toward the horizon. And he’s not the only one; 75% of all cruisers have already left. Some back to Europe, some North, others South, and a few to the East… The high season of Caribbean sailing is coming to an end, and hurricane season is rapidly approaching.

The Season is Changing: Hurricane Season is Coming

For sailors living on a sailboat, hurricane season means one thing: you either leave or you stay and make peace with the risk. Right now, boats all around us are preparing to cross the Atlantic. First stop: the Azores. Then back to Europe. Not that we want to go back to Europe, but watching people set off toward open water? That stings a little!

That’s why we chose this life in the first place. The wind, the waves, the freedom to go wherever the charts lead. And yet, here we are. Staying put. It wasn’t an easy decision, but it was the right one for now.

Why We Left Recruitment Behind

For the past few years, we worked as independent recruiters. On paper it sounds great: remote work, no ceiling on income, full flexibility. The reality was something else entirely.

We worked as 360° recruiters, that meant we had to find our own clients, source our own candidates, run our own marketing, everything. Out of roughly 250 interviews, there came maybe 5 placements. Sometimes less. Every candidate felt like a breakthrough.

Every rejection took something with it. And even if the candidate was hired by the company, the deal could still fall through at the last minute. No placement, no income. We worked every single day, and by the end of the year, we barely had enough to cover the basics, nothing left for the boat, for repairs, for the future we are trying to build.

When Everything We Built Collapsed.

The real breaking point came when the company we worked for went bankrupt while we were in the middle of crossing the Atlantic. We were owed around €17,000 in commission, money we had already worked very hard for. We never saw a cent of it.

We arrived in the Caribbean needing money urgently and starting from scratch, again. We did try to rebuild. An old colleague came up with the idea of starting our own agency, and we went for it. But something had shifted. The joy wasn’t there anymore. Every day felt like pushing a boulder uphill, and we were doing it alone. So we decided to stop.

What We’re Building Now

We’ve started something new; a business built around what we’re actually passionate about. We help people who are thinking about buying a sailboat to make the right decision before they sign anything.

We’re not surveyors, but we work as a kind of pre-surveyor: someone who sits down with you, understands what you actually need, and helps you avoid expensive mistakes that come from buying the wrong boat for your life.

Of course, this takes time to build, so in the meantime, we’ve stayed close to what we love. I (Lotte) went looking for work here in St. Maarten, something hands-on, something that would teach me real skills. I ended up at a rigging company, climbing masts and learning the craft from the ground up. They’ve been talking about placing me with a professional rigger, which would be an incredible opportunity.

The only uncertainty is that the rigger in question might be leaving soon, so we’ll see. Ramon, meanwhile, has landed a fully remote job… Things are moving, even if slowly.

The Plan

Our goal is clear: use 2026 and 2027 to build real income, invest in the boat, and grow our online business, so that we can keep doing what we actually want to do. Sail! Not as a holiday, but as a life.

Every sailor figures this out differently. Some leave now and sort the money out later. Some build first, then go. This is our way. Does it sting sometimes, watching other sailors head for the horizon while we stay behind? Absolutely. But we’re building something. We’ll keep sharing the honest version of all this;

– The wins,
– The setbacks,
– The slow days
– And the breakthroughs.

You’re welcome to come along for the ride. Subscribe and you’ll receive an update when a new blog is out. And if you’d like to support our journey, you can always buy us a beer. 🍺