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Travel + Leisure

Sydney’s Central Business District and its immediate surroundings are a magnet for visitors to the Australian capital. In just over one square mile, you’ll find some of the city’s most iconic sites, like Circular Quay harbor, the Sydney Opera House and The Rocks (a picturesque, historic area with buildings dating to the 18th-century). But it’s also a place to unwind, with a collection of pubs, lounges and clubs that have opened in the last few years, making it perhaps the most exciting drinking and nightlife destination in Sydney right now. Here, a few of our favorites places for a cocktail (or three)—all within walking distance of one another, which makes bar crawling a breeze.

Lobo Plantation

Inspired by exiled Cuban sugar baron Julio Lobo, the subterranean Lobo Plantation transports guests to Old Havana, utilizing lots of potted palms, dimly lit leather banquettes and a menu of over 150 kinds of rum sourced from around the world. Even the waiters and waitresses offer a throwback to Old Havana, clad in bowties (with waxed mustaches, natch) and floral, 40s-style dresses, respectively.

Ivy

So much more than just a place to grab a drink, this entertainment complex consists of restaurants, boutiques, event spaces and—best of all—a rooftop pool bar, where guests can reserve private cabanas while sipping on an Aussie Sauvignon Blanc and snacking on tuna tartare and caprese salads.

Easy Eight

The hearty, American-influenced food at Easy Eight is excellent (like the 12-hour smoked brisket and the expertly-prepared roast chicken), but it’s also a fine spot for a drink before moving on with the rest of your night. Standout cocktails include the Ultima, made with tequila, chartreuse, lemon juice and maraschino liqueur. 61-2 9299-3769

The Baxter Inn

Any bourbon drinker visiting Sydney should make it a point to stop by below-ground, speakeasy-style The Baxter Inn. There may be a line out front, but don’t let that stop you—with over 100 whiskeys from which to choose, the small wait is worth it.

Bennelong

Dinner at Bennelong is a no-brainer. It’d be enough that it’s located in the city’s icon, the Opera House. But the fact that it also offers the very best of Australia’s bounty—Sydney rock oysters with lemon and pepper granita, grilled Tasmanian octopus with smoked almonds—make it a culinary must.

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