Cozy Up at Calissa Chalet: An Après-Ski Escape in the Hamptons

Cozy up to an Alpine menu at Calissa Chalet, Calissa’s après-ski-inspired winter makeover. Each season, Calissa transforms from a sunlit, rosé-on-the-terrace hotspot into a candlelit, cold-weather escape. In the Chalet Lounge, guests settle in with hot toddies, mulled wine, decadent fondue, and crisp fritto misto, all set against a backdrop of soft sheepskins, candlelight, and low, convivial buzz. It’s an intimate, transportive jewel box of a room, equally perfect for an early evening spiked hot chocolate or a post-dinner nightcap.

Credit: Calissa

Calissa’s seasonal transformation extends into the Dining Room, where the menu leans into cold-weather comfort dishes with a Greek accent. Bowls of silky avgolemono soup arrive steaming to the table, followed by moussaka, slow-braised short rib giouvetsi, and warm apple pie with ice cream. The restaurant’s award-winning wine list comes into its own in winter, from bright, mineral Champagnes that cut through rich dishes to soulful Mediterranean reds that suit long conversations and lingering desserts. On Friday and Saturday nights, DJ performances in the Lounge give the space a dressed-up night-out energy; guests drift from dinner to the Chalet, martinis in hand, and the evening takes on the feel of a chic, Alpine house party in the Hamptons.

Credit: Calissa

For groups, the Winter Feast at Calissa is the excuse to get everyone together for a proper night out—your unofficial winter reunion. Designed for parties of six or more, the menu opens with a holiday spread that immediately fills the table: mezze, a seasonal salad, zucchini chips, and grilled octopus that keeps the conversation moving as plates are passed. The centerpiece of the evening is a choice of one showstopper—salt-baked branzino royale, Cretan-style prime rib, or whole roasted lamb shoulder—each presented with a sense of occasion and served alongside generous sides meant for sharing. Warm apple pie and ice cream close out the meal on a nostalgic note, while the team offers guests bottles from the award-winning wine list or signature cocktails that match the mood of the table. It feels celebratory without being formal, indulgent but easy: you gather the friends, and Calissa does the rest.

And for nights when you’d rather stay in, Calissa’s cuisine travels beautifully. Many of the same dishes that define Chalet season—hearty sides, roasted meats, abundant mezze, and warming desserts —are available for takeout, turning a quiet evening at home into something that still feels special. Light a few candles, uncork a bottle, unpack the bags, and let Calissa handle dinner.

Credit: Calissa

For the rest of the season’s gatherings, Calissa is an easy place to bring everyone together. Host everything from breakfast meetings and chic brunches to long lunches and cocktail-driven happy hours in the Chalet Lounge, the main Dining Room, or at the bar. After-parties flow naturally from dinner into DJ nights, with late-night snacks and another round of drinks at the ready. Throughout it all, Calissa’s blend of Mediterranean comfort, thoughtful hospitality, and quietly polished service turns winter in the Hamptons into an invitation to go out and be merry.