The Rooftop at The Envoy has solidified its reputation as the premier winter destination in Boston’s Seaport District by successfully delivering the festive spirit of the outdoors without the accompanying chill. Perched seven levels above the harbor, the rooftop’s highly sought-after heated winter igloos—or “Glasshouses”—offer an intimate and luxurious escape set against a breathtaking panoramic skyline.
Escaping the Winter Chill
General Manager Chris DeMilia explained how the temporary structures transform the typical open-air experience of the roof: “The heated winter igloos completely transform the guest experience by creating a warm, cozy escape from the cold—almost like slipping into a private tent the way you did during childhood campouts.” He noted the shift from summer’s communal feel: “Instead of the wide-open, social buzz of a summer rooftop, the igloos offer an intimate hideaway where you and your friends can laugh, swap stories, and feel tucked away from the general public.” The ambiance is key to the holiday atmosphere: “With soft lighting, festive décor, and holiday accents glowing all around you, the space feels magically insulated from the winter chill. It’s the perfect setting to sip spiked hot chocolate, reminisce with friends, and enjoy the season in a way that feels both playful and luxurious—an experience that doesn’t exist in the summer months.”
The igloos’ success in the Seaport District is due to their versatility for various gatherings at The Envoy. “As one of Boston’s most sought-after rooftops, the winter igloos have become a premier choice in the Seaport because they offer something for everyone,” DeMilia said. The destination balances atmosphere, location, and amenity: “That balance of warmth, privacy, and unforgettable scenery is what makes them the go-to setting for date nights, celebrations, and festive gatherings throughout the winter season in the Seaport District.”
Designing the Gin-gle All The Way Experience
This year’s theme, the “Gin-gle All The Way Igloo Experience,” was developed in partnership with Empress 1908 Gin. DeMilia described the process of translating the spirit’s qualities into the physical space: “Empress 1908 Gin is often described as the perfect harmony of exquisite taste, delicate aroma, soft texture, and remarkable presentation—and we used those very ideals as our blueprint when creating the winter igloo experience.” He detailed the results: “Every element inside the pods was intentionally chosen to bring the spirit of Empress to life in a physical, immersive way. Soft, warm blankets; the subtle scent of Douglas Fir; brilliant blue and white lighting; and shimmering star-like accents wrap each igloo in a magical glow, transforming it into your own private winter wonderland.”
The bar’s compelling and warming winter beverage menu is crafted through a careful, collaborative process with The Envoy. “We’ve been crafting winter menus for eight years now, and it’s still one of the most fun parts of our jobs,” DeMilia shared. He gave a detailed look at some of the popular selections, including the Gin-gle Bell Hot Toddy: “This cocktail is the definition of winter comfort. The warmth of the hot toddy base, paired with honey, fresh lemon, and holiday-spiced syrup, instantly evokes the cozy feeling of being wrapped in a blanket on a cold night.”
Maintaining Rooftop Luxury
The challenge of placing small, temporary structures on a chic rooftop requires continuous effort to uphold the hotel’s luxury standard. DeMilia noted the advantage of their partnerships: “We’re lucky to work with amazing brand partners each season, which helps us keep the igloos fresh, elevated, and perfectly aligned with The Envoy’s overall vibe. Everything inside the igloos is reimagined each year to feel new, intentional, and on-brand.” While essentials provide comfort, the creative freedom allows for layering: “That freedom allows us to layer in luxurious textures, thoughtful lighting, seasonal design elements, and small touches that make the igloos feel just as chic and polished as the rest of the rooftop, while still being warm, intimate, and inviting.”
