How to spend 3 days exploring Sydney’s most iconic precincts

Sample world-class food and coffee, marvel at eye-opening cultural moments and meet friendly locals on a three-day tour of Sydney’s iconic precincts.

Destination NSW

Destination NSW

Sep 2023 -
min read

There’s no better way to get to know Sydney than by exploring the characterful inner-city spots where its residents dine, shop and play. Each area has a distinct personality, from sophisticated Surry Hills to bustling Barangaroo and edgy Newtown. Each pocket boasts fabulous food, strollable streets and abundant architectural beauty.

Together, these suburbs sum up what makes Sydney so special. Here’s how to discover them.

DAY ONE: Barangaroo, Darling Harbour & Darling Square



Shortstop Coffee and Donuts is located at

  • 3/23 Barangaroo Avenue
    Barangaroo NSW 2000
  • It’s a 10min walk from Wynyard Station
Shortstop Coffee and Donuts Darling Square


Begin your journey of discovery in a revitalised harbourfront zone that’s steeped in history. Once home to a sprawling container terminal, Barangaroo is now a vibrant mini-city dotted with apartments, offices, luxury hotels, and some excellent dining and shopping options.

Pick up breakfast at Shortstop Coffee and Donuts, a Sydney doughnut favourite loved for its glazed treats and specialty coffee. Then stroll along the water’s edge to Barangaroo Reserve, a park landscaped with 75,000 native trees and shrubs. Here, you can join a Barangaroo Aboriginal Cultural Tour and learn about the harbour’s rich Aboriginal history, or go for a swim in the harbour pool, Marrinawi Cove.

Credit: Shortstop Coffee and Donuts Darling Square

Donut and coffee at Shortstop Coffee and Donuts Darling Square - Credit: Shortstop Coffee and Donuts Darling Square

Don’t leave Barangaroo without exploring the southern laneways, where you’ll find boutiques selling threads by local and international designers and the expansive Title bookstore.


It’s a short walk from Barangaroo to buzzy Darling Harbour, where some of Sydney’s top cultural attractions rub shoulders with an array of restaurants and cafes. Grab lunch from one of the popular open-air eateries that overlook the water at the Harbourside shopping centre.

Once you’ve refuelled, stroll over to the Australian National Maritime Museum, which maintains a spectacular collection of historic vessels including a Cold War submarine. Or, for a different kind of aquatic adventure, visit Sea Life Sydney Aquarium and marvel at more than 700 different species of sea creatures.

Dugong in SEA LIFE Sydney Aquarium

Dugong at SEA LIFE Sydney Aquarium, Darling Harbour


In recent years, the area adjacent to Darling Harbour, known as Darling Square, has emerged as one of Sydney’s liveliest after-dark destinations. Kick off your evening with a drink at Batch Brewing Company where you can explore its extensive beer range (plus some of the team’s favourites from other breweries).

Darling Square - Little Hay Street

Darling Square, Little Hay Street - Credit: The Streets of Barangaroo

For a memorable dinner experience, book a table at The Eight, a cavernous Cantonese restaurant sitting at the top of Market City, and which has become famous for its roast duck, fresh seafood and fantastic yum cha since it opened its doors. Alternatively, head to Arisun for Korean fried chicken, Mamak for wafer-thin roti and Dopa for a fast, fresh and unexpected Japanese dining experience.

Dopa - Credit: Concrete Playground | Devon Garden City Pty Ltd Darling Quarter

Dopa - Credit: Concrete Playground | Devon Garden City Pty Ltd Darling Quarter

Cap off your evening with a scoop of gelato from the Darling Square outpost of Messina, the cult Sydney ice-cream chain famous for its one-off flavours, such as mango pancake and cream cheese with red velvet.

Gelato Messina, Darling Square

Gelato Messina, Darling Square - Credit: Gelato Messina

DAY TWO: Kings Cross, Potts Point, Darlinghurst & Surry Hills



Shady Pines Saloon is located at

  • 4/256 Crown Street
    Darlinghurst NSW 2010
  • It’s a 10min walk from Museum Station
Inside the Shady Pines Saloon - Darlinghurst


Kings Cross, an atmospheric enclave within the suburb of Potts Point, is Sydney’s original 24-hour neighbourhood. No matter what time your day begins, you can count on Pina for excellent coffee and breakfast fare.

Soak up the Parisian atmosphere as you wander the avenues of Potts Point and nearby Elizabeth Bay, which are lined with homewares stores (like Macleay on Manning and Becker Minty), art deco apartment buildings and colonial mansions dating back to the 1830s.

Friends enjoying a day of shopping at Becker Minty in Potts Point, Sydney City

Becker Minty, Potts Point


Hop in a taxi or ride share and head for nearby Surry Hills, a leafy locale that has long served as Sydney’s restaurant mecca. For lunch, look no further than Bills, the original home of super-chef Bill Granger, whose repertoire of brunch classics – including ricotta hotcakes and corn fritters – is available til midday.

Ricotta hotcakes from bills

Ricotta hotcakes from bills, Surry Hills

Bills is on Crown Street, which also hosts some of the city’s best independent retailers, from contemporary interiors store Hay to men’s and women’s fashion emporium The Standard Store.

Once you’ve had your retail fix, get a dose of culture at the Brett Whiteley Studio, where one of Australia’s most celebrated creatives lived and worked in the 1980s and 1990s. Alongside a selection of Whiteley’s work, there’s a trove of personal effects and sketchbooks that shed light on the enigmatic artist.

A man admiring artworks at Brett Whiteley Studio in Surry Hills, Sydney

Brett Whiteley Studio, Surry Hills


Adjacent to Surry Hills, hip and happening Darlinghurst provides dining and entertainment options galore, much of it located along Oxford Street. This is where the world-famous Gay & Lesbian Mardi Gras Parade takes place each March, and where Sydney’s LGBTQIA+ community congregates all year-round. Whatever your identity, you’ll be warmly welcomed.

Sydney Gay and Lesbian Mardi Gras - Sydney

Sydney Gay and Lesbian Mardi Gras Parade - Credit: Jeffrey Feng

Kick off the evening with a drink at the trendy Shady Pines Saloon, if you can find it: this speakeasy-style bar is hidden behind an unmarked door. Then stroll to Bar Vincent, a Euro-style bistro offering Italian fare and natural and minimal-intervention wines.

Credit: Shady Pines Saloon

Inside the Shady Pines Saloon - Credit: Shady Pines Saloon

Afterwards, settle in for the night at one of Darlinghurst’s renowned entertainment venues, such as live-music den Oxford Art Factory or the beloved Darlinghurst Theatre Company, which hosts edgy theatrical and musical performances.

Patrons enjoying live music at the Oxford Art Factory in Darlinghurst, Inner Sydney

Oxford Art Factory, Darlinghurst

DAY THREE: Newtown & Enmore



Route 66 is located at

  • 2/82–84 Enmore Road
    Newtown NSW 2042
  • It’s a 6min walk from Newtown Station
Out the front of Route 66 in Newtown, Inner Sydney


Students, musicians and bohemian families have long flocked to Newtown and its neighbour Enmore, giving the area a distinct vibe. It’s also where you’ll find top-notch casual food from all over the world.

Street art in Newtown - Phillip Street mural

Street art in Newtown - Phillip Street mural

Begin on Enmore Road with breakfast at Azuki, a Japanese bakery known for its artisan bread and cakes. Then amble towards Newtown, popping into shops such as Route 66 for vintage clothing and Collectika for a mix of vintage and new homewares and furniture.


You’ll soon arrive at King Street in Newtown, where the shopping is eclectic, the people-watching is fantastic and the dining options are endless. Work up an appetite by walking to the lesser-visited southern end of the strip and checking out niche retailers such as The Wilde Merchant (for vintage clothes) and Repressed Records.

For lunch, choose from one of Newtown’s numerous Thai restaurants such as institution, Ladda’s, or seek out Continental Deli Bar and Bistro and order charcuterie, smoked anchovies and cheese to graze on. Wherever you dine, skip dessert and proceed to the final stop on your tour of Sydney’s iconic precincts: Mapo, one of the best gelaterias in the city where the ingredients are all natural and many of the gelato flavours are vegan, but don’t seem it.

For an early dessert (the shop closes at 6pm), head to Black Star Pastry. It’s here you’ll find the legendary Strawberry Watermelon Cake, a heavenly creation topped with rose petals. Like Newtown itself, the iconic dessert is one of a kind. Endings don’t come much sweeter than this.

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