For most, Thanksgiving means turkey, football, and family gatherings. But for my wife, Jessica, and me, it has come to mean something different. Along with our crew of eight from Del Ray—six of us from Leadbeater Street—we once again traded the chilly November air for warm Caribbean breezes, setting sail in the turquoise waters of St. Vincent and the Grenadines (SVG), a stunning Caribbean nation of 32 islands.

Our home for the week was the Sunchill, a Lagoon 45 catamaran. It was a bareboat charter, meaning no hired crew—just us, the open ocean, and the wind. The boat was surprisingly comfortable, with four cabins, each with its own bathroom, plus a fully equipped kitchen, oven, grill, and even a water maker converting seawater into fresh drinking water. I captained, with Eric—an experienced Swiss sailor—as first mate. Also aboard were Andy, Maura, Chris, Veronica, and Lexie, a fantastic crew of neighbors who made the adventure even more special.

Sailing can be incredibly eco-friendly. We used our motors only to enter and exit marinas or to anchor, relying entirely on wind power the rest of the time—burning just $50 worth of fuel for the week. On a boat, waste management is a challenge. Every piece of trash stays with you until shore, making us rethink consumption, plan meals carefully, and minimize waste. The experience highlighted how much unnecessary waste we create in daily life and how simple adjustments make a difference.

This year, thoughtful planning was even more crucial. Hurricane Beryl, a Category 5 storm, devastated parts of the Grenadines in July, leaving beach bars and restaurants in ruins. Some islands still hadn’t fully recovered; we couldn’t rely on stores for last-minute supplies. Supporting local businesses felt even more meaningful.

Our daily rhythm was simple: wake up, make breakfast, and set sail around 10 a.m., with sails lasting one to three hours. Once anchored, the ocean became our playground—swimming, floating on the Sunchill (the best water toy ever made), taking the dinghy to a beach bar, or simply relaxing. The freedom of a bareboat charter meant we could go anywhere—if a spot wasn’t great, we’d pull up anchor and move on.

This wasn’t our first sailing trip—we’ve explored the Gulf of Mexico, the British Virgin Islands, and the Spanish Virgin Islands. Since our first adventure, Jessica and I have dreamed of owning a catamaran and sailing part of the year.

Meeting friends who live on their boat with their dog made it feel more tangible. Also, our friend Hans, who introduced me to sailing, bought a catamaran in Europe, crossed the Atlantic in December, and now lives aboard full-time.

What once felt like a distant dream now feels like a long-term plan waiting to be set in motion. For now, our Thanksgiving sailing trips keep that dream alive. But maybe one day, instead of returning home after a week at sea, the sea will be home.