A 3-day itinerary in Sydney for arts & culture

Morning 

Start your day with a visit to the White Rabbit Gallery in Chippendale, which presents four floors of vibrant, original, thought-provoking art. The gallery’s collection includes paintings, photography, sculpture, video art, drawings and installations. It also houses one of the world’s most significant collections of Chinese contemporary art. The Teahouse on the ground floor offers simple dumplings and tea, in case you need to fuel up before perusing the exhibitions. 

White Rabbit Gallery, Chippendale

If you still have some time on your hands before check in, just two minutes away from White Rabbit you’ll find Harrington Street Gallery, another free-entry gallery. Established in 1973 by artist John Ogburn in Harrington Street, The Rocks, this artist cooperative moved to its Chippendale location in 1986. Conceived as an independent way to showcase work by both established and up-and-coming artists, the gallery remains a beloved destination for local art enthusiasts. 

Harrington Street Gallery, Chippendale

Afternoon  

Replicating the bustling, casual atmosphere of a Southeast Asian hawker market, Spice Alley is a great inner-city spot to try a range of street food come lunch time. Nab a plate of dumplings, a smoky char kway teow, a roti with curry or a hearty ramen and explore the hollowed-out old Kensington Street homes and the alleys in between. 

Spice Alley, Chippendale

Arrive at The Old Clare Hotel and check in to the Showroom Suite, complete with a heritage bar, salvaged and restored from the former brewery building on site. The beautifully appointed, design-forward room includes vintage furniture and lamps, a super king-sized bed and a modern oversized bathroom complete with a tub. Before heading out for the evening, head to the hotel’s rooftop bar to dip your feet in the pool with a cocktail in hand. 

The Old Clare Hotel in Chippendale - Credit: The Old Clare Hotel

Evening 

Book in for an early dinner at Chin Chin, a Surry Hills restaurant melding Australian and Southeast Asian flavours in a modern converted warehouse space. Try its tasting ‘Feed Me’ menu for a selection of the venue’s favourite dishes to share. 

Chin Chin, Surry Hills - Credit: Steven Woodburn

Catch an evening show at Belvoir St Theatre, one of Australia’s most respected theatres, with Cate Blanchett and other stars gracing its stages. Since 1984, this much-loved venue has engaged prominent and promising playwrights, actors and directors for an evocative annual artistic program. 

Couple enjoying a night out at Belvoir St Theatre, Surry Hills

Morning 

Soak up the culture of the Inner West, starting with breakfast in Newtown. Nestled in the suburb’s leafy backstreets, Soulmate is a much-loved, sunny cafe serving delicious brunch and really great coffee with generous service. Don’t leave without trying the McHenry – a hot or cold black coffee topped with whipped cream. 

Soumate Cafe, Newtown

Take a self-guided walk through Newtown’s back streets and alleyways to check out its ever-changing street art. Or let the experts show you the way by joining the three-hour guided ‘Newtown Chewtown - Food and Street Art’ tour with Local Sauce Tours. Either way, be sure to get a picture of the iconic ‘I Have A Dream’ mural by artists Andrew Aitken and Julie Prior on King St, which is now heritage listed (for more street art in Sydney, follow our guide here). 

Street art in Newtown - Phillip Street mural

Afternoon  

Head to the buzzing Enmore Road for lunch, where you can pick and choose between a huge range of cuisines and price points. Try Bar Louise for Spanish share plates; Colombo Social for Sri Lankan roti tacos and lassis; Cairo Takeaway for Egyptian street food; the Duke of Enmore for a pub feed; The Stinking Bishops for cheese and charcuterie; and Little Turtle for vegan Thai, just to name a few. 

Cairo Takeaway, Enmore

Now it’s time to shop til you drop among the unique boutiques, bookstores and vintage shops in Newtown. Explore Reunion, SWOP and U Turn for second-hand clothes; Hands for lifestyle gifts; P&V Wine & Liquor for Australian and imported natural wines; Better Read Than Dead and Elizabeth’s for books; Repressed Records for vinyl; and much more. 

Elizabeth's Bookshop, Newtown

Evening 

Find your inner drag queen at The Imperial, a jewel of the Inner West and the LGBTQIA+ community. Join the fun at a Drag and Dine show (running every night from Wednesday to Sunday) – you may even be called on stage for an impromptu performance. After dinner, head downstairs to the Basement to dance the night away. 

The Imperial Erskineville, Erskineville

Morning 

Make tracks for Henry Lee's in Redfern for breakfast, a truly creative space located in the 16 Eveleigh Creative Precinct. Admire original artworks including ‘Lucky Penny’ designed by Vince Frost of Frost Collective. 

Afterwards, head over to the Art Gallery of NSW to see its latest exhibitions and its latest space, the North Building – a new standalone building that nearly doubles the gallery's architectural footprint and exhibition space. 

People visiting the Art Gallery of New South Wales, Sydney 

Afternoon  

Walk through the scenic Royal Botanic Garden and make your way to The Rocks, enjoying views of the city’s icons – the Opera House and Harbour Bridge – along the way. With the arrival of European settlers in 1788, it was here that the convicts originally set up house and shop. The best way to discover the area’s colonial history is on foot as you amble along cobbled streets and follow little laneways that house everything from markets to museums. 

Come lunchtime, pull up a stool at the pubs where Sydney’s first settlers used to drink (and are some of the oldest in the city) , like the Fortune of War, The Hero of Waterloo, The Glenmore Hotel and the Lord Nelson Brewery. 

The Glenmore Hotel, The Rocks - Credit: W. Short Hotel Group

Afterwards, discover one of Sydney’s major modern art venues, the Museum of Contemporary Art (MCA), which hosts regularly changing exhibitions by major international artists such as Annie Leibovitz, Anish Kapoor, Yoko Ono and Grayson Perry. Free guided tours are conducted each day, visit the information desk on Level One for the scheduled times. 

Museum of Contemporary Art, Circular Quay - Credit: Anna Kučera

Evening 

End you arts and culture play-cay with drinks, dinner and a show at The Vanguard, located back towards your accommodation in the Inner West. An intimate venue holding less than 100 people make it well-suited for a night of blues, jazz and folk music, but performances also range from burlesque to author workshops, so be sure to check the calendar to see what’s on during your visit. For an after-show, late-night tipple and boogie, stop by the Pleasure Club, the first Newtown bar to be granted regulatory approval to trade until 4am, seven days a week, in more than 100 years. 

Patrons enjoying drinks and live music at The Vanguard, Newtown