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Wine Banq
This place looks like an architect's dream bunker and a brilliant wine list only adds to the appeal. It's the sexiest spot to hear live jazz in Sydney. Past performers have included Wynton Marsalis, Barbara Morrison and Harry Connick Jr, but you'll catch lesser luminaries several nights a week.
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Woollahra Hotel
It's a bit snooty and suity most of the time, but it's certainly worth checking out the free live Latin, jazz and Brazilian funk on Sundays and Thursdays.
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World Bar
Three floors of cool spaces attract the backpacking crowd (especially on Tuesday's Krapp Karaoke night) to this former bordello, and cheap drinks keep them rockin'. There's an airy tropical terrace out the front, different genre DJs nightly (electro, indie, hip-hop, boogie house) and live indie bands on Fridays.
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Zanzibar
Eastern opulence continues all the way to the roof in Newtown's late night option. Catch the sublime sunset views from the rooftop, settle into a cushioned couch or shoot some pool in the downstairs bar.
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Zeta
Ride the Hilton escalators up to Zeta, which captivates a chic young city crew with its white vinyl lounges, discrete curtained booths (what was Snoop Dog smoking in there?) and enormous gas inferno. Sip grilled-fruit cocktails and eyeball the QVB dome from the terrace.
