Long after the last beach umbrella is folded and the summer crowd drifts back to the city, Calissa remains one of the few places in the Hamptons that refuses to dim its light. In fact, winter is when the beloved Water Mill gem feels most compelling—a glamorous, glowing refuge where the energy shifts from seaside buzz to something richer, cozier, and irresistibly cinematic. This season, that allure centers on two of Calissa’s most talked-about experiences: the Chalet and the Winter Feast.
The Calissa Chalet has become a cold-weather ritual for those who appreciate the quiet luxury of the off-season. It’s an alpine-inspired hideaway wrapped in candlelight, faux-fur textures, and an air of polished escapism. Think ski-lodge fantasy, but edited through a Hamptons lens: warm, intimate, and designed for lingering. The cocktails arrive steaming or shimmering, the playlists lean toward European après-ski, and every table carries that unmistakable feeling of being exactly where you want to be. It’s the sort of place where a casual weeknight suddenly feels like a weekend, and where the line between dinner and celebration pleasantly blurs.
Then there’s Calissa’s Winter Feast—an annual ode to abundance that manages to feel both indulgent and deeply comforting. This is not a menu built on gimmicks, but on dishes that invite you to settle in: slow-braised meats, rustic Greek favorites, and the kinds of seasonal flavors that taste even better against a backdrop of frost-tipped evergreens. The Feast embodies what Calissa does best: taking traditional Mediterranean warmth and elevating it into something sophisticated, soulful, and perfect for a long winter night.
But perhaps the real magic of Calissa in winter is the way it transforms the Hamptons’ quiet season into a moment of possibility. While most of the East End winds down, Calissa feels alive—buzzing with locals, weekenders, and those in the know who’ve discovered that the best time to be here is right now. It’s a place to host friends, toast the end of the year, or simply escape from the cold with a meal that feels like a small luxury.
In a season defined by calm and candlelight, Calissa stands as the Hamptons’ most stylish winter sanctuary—warm, inviting, and effortlessly glamorous. Click here for more.
