The Best Winter Cocktail Bars In Pittsburgh, Pennsylvania

Who would’ve thought that there’d be a tropical oasis in the middle of Pittsburgh? Well, Kaya is just this. Refresh yourself with fruity sangria, margaritas, a mai tai, mojitos, and more fun Caribbean drinks, all complete with a tiny umbrella. If you want to keep it simple, beer, wine, rum, scotch and tequila are also featured on the extensive drinks menu. Be sure to check out their daily happy hour to get half-off the regular price. Additionally, Kaya serves delicious, eclectic Caribbean cuisine. Stop by for lunch, dinner, or weekend brunch. Brunch comes complete with early-morning drinks, like mimosas and Bloody Marys.

You’re guaranteed to find one or two James Bond-esque gentleman at this intimate martini bar and lounge. At Olive or Twist, you can have your drink shaken not stirred, sweet or tangy, and strong or stronger. The lounge provides an alluring atmosphere, with industrial brick walls and chic, modern decor. Curl up in a private booth or sit at the bar, and engage in stimulating conversation with a few Pittsburgh locals. There are more than 20 different kinds of martinis on the menu, in addition to wine, beer and other ‘on the rocks’ drinks. For food, order anything from nachos to filet mignon. But, whatever you do, don’t miss out on the almond cream cake.

Less is more at Bar Marco. Step into a classy yet comfortable environment and enjoy a refreshing cocktail alongside a tasty bite to eat. The Bar Room features a few specialty cocktails and delicious meals, such as scallop risotto and steak. Also open on the weekends, this is a popular place for brunch, where guests may dine on smoked salmon Benedict and corn pancakes. But this is just the Bar Room – Bar Marco is made up of both the Bar Room, and the Wine Room. More on the exclusive side, the Wine Room is reservation only with a tasting menu and wine pairings. The prix fixe experience is two-hours of dining on a seven-course, seasonal menu, with wine specially paired for each course. This is no honky-tonk or tavern, but it’s a great place for a special, elite experience.

Set in the OMNI William Penn Hotel, this cosy spot really lives up to its name. With dark interiors and an authentic look, you’ll like you’re stepping into the past as you enter via a discrete doorway. The high-end lounge inspires a 1920s ambiance thanks to plush, rouge upholstery and think carpets. The drinks, which is what we’re really after, are period appropriate with relevant modifications where necessary. This isn’t the cheapest offering on our list – you might end up wishing you were back in the prohibition era when the bill arrives – but you won’t regret it.

Reminiscent of a warehouse, this industrial-styled pub isn’t what you think. Rather than dank and dark, the pub is open and inviting. The brick walls are beautifully paired with creative lighting, large windows and open seating. The menu features more than 15 signature cocktails, 40 beers on tap, more than 20 wines, and what seems to be an infinite amount of whiskey. Bring your friends and coworkers to happy hour to enjoy drinks and food at a reduced price. Speaking of food, Industry Public House serves delicious American fare such as wings, flatbreads, burgers, and even tastier dishes. This is also a popular place for brunch, so make a weekend reservation to enjoy all the morning drinks available.