Play hide and seek in secret bars 

From whisky-soaked speakeasies to exuberant jazz dens hiding in plain sight, Sydney’s secret waterholes reward those who know where to look – and are bold enough to push the door. Start in the YCK Laneways precinct – stretching between Wynyard and Town Hall in the city centre – where more than 20 small bars and eateries are packed into a colourful labyrinth of historic alleys. 

On the edge of the city, following the Inner West Ale Trail through Newtown, Marrickville and Camperdown leads to 17 of Sydney’s best breweries, each with their own take on tippling, from the industrial charm of Wayward to the warehouse chic of Batch, and the rock’n’roll vibe of Young Henrys. While you’re in the neighbourhood, swing by Jacoby’s Tiki Bar for tropical drinks and glowing décor, and LazyBones Lounge for live jazz, an eclectic cocktail list and velvet-draped interiors that make every winter night cosy.  

Closer to the harbour, the hidden bars are just as theatrical. In The Rocks, The Doss House pours 150-plus whiskies in a 170-year-old sandstone building that once housed an opium den. In the city’s heart, Apollonia is tucked beneath Hinchcliff House – a moody, candlelit bar with Italian cocktails and cured meats, while around the corner, Double Deuce Lounge channels 1970s swagger with red leather booths, a furry wall and a funky playlist. 

Across the water in Manly, The Cumberland hides behind a fridge door and leads to an intimate, Spanish-style bar with more than 250 whiskies and an inviting interior lined with stone, brass and leather. In a city known for its bold views and bright lights, these tucked-away spots invite you into Sydney’s invigorating winter energy – one artfully muddled sip at a time.  

Drink in the world-class views 

Refresh your winter perspective at one of Sydney’s rooftop bars, where you can become part of the skyline while the city’s lights unfurl below like an open invitation. On the harbour’s edge, you’ll find a host of hotspots where the views are elevated in every sense. Aster Bar is located on the 32nd floor of the InterContinental Sydney and offers 270-degree views of the Royal Botanic Garden and Sydney Opera House – best enjoyed with a bespoke martini in its glamorously appointed lounge. Over on Millers Point, Henry Deane crowns the Hotel Palisade with creative cocktails, plush lounges, sun-drenched balconies and uninterrupted views in every direction. And at Smoke, atop Barangaroo House, the imaginative drinks list matches the glittering winter backdrop, with signatures like the Chilly Evenings (milk-washed Wild Turkey, St Germain, cloves and lemon) and the Skyline Spritz (Bombay Sapphire, raspberry, mango and bubbles). 

Nearby, The Library Bar enhances the intrigue of its secretive location with Hunter Valley wines, local gin and views stretching over the Domain and Sydney Harbour, while The Rook remains one of the city centre’s most sought-after eyries, celebrated for its standout cocktails, gin events and neon skyline panoramas.  

On the inner-city fringe, Lottie brings mezcal and modern Mexican to the rooftop of The EVE Hotel in Redfern, with an alfresco setting built for all seasons and urban views that feel close enough to touch. In Potts Point, The Butler presents sprawling city vistas from its charming terrace, alongside a zesty Ibero-American menu and thoughtful cocktails in a space layered with history and character. Further west, Nick and Nora's rises above Parramatta with a touch of Gatsby opulence – chandeliers, drinks trolleys and jaw-dropping views stretching all the way to the Blue Mountains.  

Cosy up in a buzzing a pub 

Whether you’re up for a round of community trivia, banter-filled brews with the crew or a quieter one chatting around the neighbourhood’s favourite fireplace, wherever you land in Sydney, the refreshments and memories are both on tap in its cosy pubs. In the heart of the city, The Duke of Clarence channels the feel of an 18th Century London tavern, complete with antique accents, dark wood, leather banquettes, cask ales, creative cocktails, and an award-winning menu of British fare. Across the harbour at Manly’s Hotel Steyne, locals get together in beachside courtyards, sports bars and rooftop terraces to catch live DJs, watch the game, and flex their ping pong skills. 

Flanking the city centre, buzzing neighbourhood bars invite you into heritage buildings that feel like the community’s rumpus room. With its roaring fireplace, sunny dining room and relaxed upstairs lounges, Glebe Hotel has been wetting local whistles since 1862. Likewise, Waterloo’s Cauliflower Hotel has been the heart of its community since 1838, now serving craft beer and trivia alongside an 18-screen sports bar. 

Moving east, the heritage pubs go back even further. The Paddo Inn has served good drinks and tasty pub classics since 1814, its huge windows still offering a front-row seat to the fashion, colour and creativity of Oxford Street. Nearby, the Lord Dudley leans into its old-world charm, with a red-brick façade, timber bar, crackling fireplaces and famous pot pies – a traditional English-style pub tucked into the backstreets of eclectic, electric Paddington. 

Where to cheers and cheer on your team 

Sydney’s jam-packed calendar of sporting events spreads the winter cheer far and wide – and watching a showdown from one of its legendary sports bars feels like plugging into the city’s heartbeat. Strangers become teammates, and mates turn into friendly rivals, when the action heats up. 

With more than 50 LCD TVs, three mega-screens, stadium-style sound and a lively atmosphere, The Star casino’s 24/7 Sports Bar is a prime spot for everything from international MMA bouts to footy clashes and motorsport showdowns. In the city centre, Cheers Sports Bar is a 24-hour hub for local and international fixtures across football, basketball, surfing, soccer, golf, hockey, tennis, cricket and more – with three levels making it a go-to for any game, any time. Just a short walk away, York 75 delivers a classic sports bar vibe with private booths seating up to eight, each with its own TV for a personalised viewing experience. 

Further afield and overlooking the beach, Coogee Bay Hotel’s Sports Bar adds a coastal twist to the big-game buzz, with 15 screens – including two mega-screens – and an elevated pub-grub menu to keep you cheering, while tap beers, local spirits and a solid wine list help soothe a voice well-used. And in the Inner City, Surry Hills’ Clock Hotel and Newtown’s Marlborough Hotel both offer multiple screens and effervescent, character-filled spaces that draw in like-minded fans and regulars alike.