Sipping cocktails outdoors is now a year-round activity thanks to the Lookout Rooftop at The Envoy Hotel. The always popular Seaport hot spot has brought back its pop-up igloos for what’s likely to be another frigid winter in Boston. Revelers can now party on a rooftop while taking in an amazing view of the harbor—without having to endure the brisk temperatures. Seating between eight to 10 people and available on a first-come, first-served basis, each igloo is heated and comes with cable knit blankets so that everyone can stay nice and cozy. Guests can also order drinks by pressing a button that illuminates the neon lights in the very instagrammable igloo in order to notify a server to stop by. New for this year, the pop-up will feature an additional heated enclosure, as well as a menu of small bites. 70 Sleeper St., 617.530.1559, outlookkitchenandbar.com