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Time of the Season: Sailing Life, Guided by Wind and Weather

View from boat window

The weather is shifting, and we can feel it in every gust of wind. The storms are slowly creeping up from the Caribbean, and the northern winds are starting to chill our days. I remember last year, sailing north from the sweltering heat and humidity of Grenada. We noticed just a small drop in temperature, but it was enough to feel the seasons changing. This year, I find myself savoring those rare moments when I can still walk barefoot without the cold biting at my feet.


There’s a shift in the air, and it’s not just the weather. It’s something we feel deep in the sailing community as well. Conversations are buzzing as the great migration of sailors begins. Families like ours are preparing to head toward Annapolis for the boat show, where they gather before making the big leap south to the Bahamas and the Caribbean.

After months of sailing alone, the sudden surge of social gatherings and the return of talks about the season ahead are a welcome change. It's amazing how fast our community comes alive during these transitions.


We’ve become familiar with these migration waves. After living by the wind and weather for over two years, it still amazes me how much life revolves around the seasons. Every time, the excitement builds before the big departure. The boat gets a thorough check, we stock up on supplies, make those last-minute adjustments, and start preparing ourselves mentally for the journey. And then, of course, there’s the anticipation. Oh, the anticipation. It never gets old.


But this time, things feel different. With the way the winds are blowing, it seems like this will be our last season on the water for a while. Our long sailing journey is likely to come to a close in the Caribbean, and then we’ll embark on a new chapter – life on land, in a new country.

Writing these words, my hands shake just a little. There’s fear, excitement, sadness, and joy all mixed together. But talking about it as though it’s already happening, is the first step in making dreams come true.


In the meantime, we’re preparing for one more journey. We’ll be hauling the boat out of the water soon to do some work, making sure she’s ready for the final leg of our adventure down to the warm islands of the Caribbean. The sun is calling, and as always, we’re following it.


The beauty of living this life is that it’s always in motion, just like the tides and the seasons. We’ve learned to embrace the changes, to flow with them rather than resist. As we approach this next chapter, I can’t help but feel grateful for the experiences we’ve had and the adventures still to come. And while this may be our last season on the water for now, I know that the dreams we’re chasing are far from over.

They’re just taking a new shape, as they always do.


Brooklyn bridge in sunrsie from the river

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