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A Sailboat Christmas: Escaping Expectations and Rediscovering Joy

Dec 24, 2025

Celebrating Christmas can feel like a burden. It is a time of “shoulds” and expectations. The stress of finding presents for everyone replaces the joyful anticipation of a feast day, a sacred celebration. Pile on top of it all the end-of-year stress, admin, the final hustle, and numerous social obligations, and you find yourself being cooked in a giant pot of soup that will only be delicious to an extrovert with infinite energy and a joy for even the most menial work.

For a time, it felt that way in my family as well. We were all a little stressed, but the stress spiraled up and out as we faced each other’s expectations. A certain meal my dad had to cook, a tree that needed decorating, a house that needed decorating, the dessert tradition that required my mom to get everyone an extra gift, the fact that our heads and desires were elsewhere, and that the older generation had died. It was time for something new.

Everything shifted when we took ourselves into a new environment. Far away, off an island in the Caribbean, the four of us sat on a small sailboat as the rain poured down in the dark the setting sun had left behind. We began by placing four wrapped books on the table in the cabin. Each of us picked up one and, taking turns, we unwrapped them. After that, we each chose which book we wanted to read first, with the agreement that we would pass the book along to the next family member once we had read it.

We dressed up a little and, in a rush, climbed aboard the dinghy to get to the only restaurant on site, with only one other family eating there that night. We were free. Free of consumption, free of expectation, free of chores and decorations. Here, on the other side of the world, on water instead of soil, in the warm tropical rain instead of the wintry cold, in a boat instead of a house, we could leave everything behind and reinvent our celebration.

Since then, we celebrate back at home and we always get together. Our tradition is now an amalgam of what we enjoy the most. My sister, Serafina, and my dad drive out to the forest and get the tree with the most character. Together, we decorate the tree in an interesting way and eat the food we love most. We discuss any traditions we are unsure of. There is no expectation, there is no “should,” and everything is up for discussion if the need arises.

We are free, and the Yuletide has once more become a joyful feast of love.

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