Sydney in winter | Aiden Darling Harbour

Hotel in Sydney
Aiden Darling Harbour

20 best winter warmers for a weekend in Sydney

While Sydney is often seen as a summer destination, our city has just as much to offer in the cooler months too. If not more. You might not be diving into ocean pools on the daily (unless you’re game) but you’ll be drinking red wine by the fire, seeing some of the best art and culture the city has to offer, and getting amongst the winter festivals.




Whether it’s your first visit to Sydney or your fifteenth, there’s never nothing to do. And with winter festivals, more indoor activities than you can count, mulled wine, water activities (yes, even in winter) and cosy pubs and bars galore, we say make the most of the colder weather and discover a different side of Sydney.  


Need some inspiration on where to start? We’ve mapped out a two-day itinerary including 20 different ways to make the most out of your time in Sydney in winter. The best part? All of these are just a hop, skip and jump away from us at Aiden Darling Harbour in Pyrmont, just opposite the CBD.




Kick off your Sydney in winter extravaganza with a visit to our neighbouring suburb, Glebe. Grab a hot takeaway coffee from us at Wayfarer’s and walk your way over. Then snuggle up with a good book over some pancakes at Sappho Books Café and Bar on Glebe Point Road. As the name suggests, this hidden gem is a bookstore and café in one with a range of hidden rooms and levels full of books. Keep your eyes peeled for Charlie the cat who’s coined ‘the guardian of the books’. 


Up for something more adventurous? Book yourself onto a whale watching trip with Ocean Extreme departing from Circular Quay. Around May/June, humpback whales begin passing by Sydney on their northern migration coming from Antarctic waters to the south. This means winter is the best time to get up close and personal with these beautiful creatures.


Winter is peak whale watching season off Australia’s East Coast



Sydney is home to an array of art, historic and cultural hotspots. If you’re looking for a unique art gallery, you can’t go past the White Rabbit Gallery in Chippendale. Not only does it have interactive and intricate exhibitions, it’s home to one of the world’s largest and most significant collections of Chinese contemporary art. Stop by the Tea House on the ground level for a cup of warm Chinese tea and some handmade dumplings on your way out. Try the Princess Flower Tea for a special surprise.  


Another great stop is the Museum of Contemporary Art in The Rocks. This is one of Australia’s leading museums exhibiting the work of today’s artists. It’s home to more than 4000 works by Australian artists and has a range of temporary exhibitions throughout the year. After you’ve taken in all of the art, stop by the café on the rooftop for some coffee and cake served with the perfect view of the Sydney Opera House. There’s indoor seating with glass windows in case you need a little more warmth. 


Visiting Sydney for the very first time? You have to take a Sydney Opera House tour. These tours take you inside the different areas of the architectural icon as you learn more about the history of the building. It’s a must do when visiting this harbour city!


Take a behind-the-scenes tour inside the Sydney Opera House



If you happen to be visiting during May or June, you’re in for a treat. Vivid Sydney is one of Sydney’s biggest and most well-known festivals transforming the city into a kaleidoscope of colours. Picture art installations and light projections across Sydney’s most famous icons. Wander the streets taking in all of the art installations or buy a ticket to a musical performance or panel event. 


Interested in dining at one of the top-rated restaurants in Sydney? Head to cosy Restaurant Hubert for some of the best French cuisine you can get outside of France. Hidden behind an unassuming wooden door on Bligh Street, this restaurant is decked out in vintage décor and has live jazz for an intimate and special dinner. A friendly reminder to book this popular place well in advance.


If you’re feeling more New York than Paris, book a table at Employees Only in the city for dinner and cocktails. This New York-style cocktail bar and restaurant is home to a range of sophisticated mains and features live burlesque shows on the bar every Friday and Saturday night.  


Not finished yet? Visit some of the best bars in Sydney to keep the night going. If you’re looking for a warm mulled wine in a cosy spot, The Doss House is for you. Looking for breathtaking views? Head to Dean & Nancy on 22 for playful cocktails and city lights or over to the luxurious Aster Bar for harbour hues unlike any other. 


Warm up with dumplings and wine




Take the light rail or an Uber over to Reuben Hills in Surry Hills for breakfast. Not only do they make a mean bacon burrito, they’re home to one of the best hot chocolates in Sydney. Yes, we’re talking the Nutella hot chocolate. There’s really no better pairing than a winter’s day and a hot chocolate. 


Prefer to stay in the city? The Grounds of the City makes for a cosy breakfast and lunch spot or stop by for some coffee and cake. Situated in The Galeries on George Street, this is a Parisian-bistro-inspired café with vintage décor.



Get some much-needed rest and relaxation in at The Day Spa by Chuan. Take your pick from a range of luxury facials, relaxing massages or go all out with the Champagne and gold indulgence package. Don’t forget to take a picture in their Instagram-worthy pool featuring a painted roof made to look like the night sky. 


If you’re more of a foodie, tick off a Sydney bucket list item and have high tea at The Tea Room in the Queen Victoria Building. Set inside the stunning heritage-listed building, this high tea features a delectable selection of finger sandwiches, petit fours, pastries, and scones created by their award-winning pâtissier. If you’re up for a drink after, stop by Reign at the QVB  and try one or two of their 150 Champagnes and sparkling wines on offer. 


The magnificent Queen Victoria Building in Sydney’s CBD


If you happen to be visiting in July, head down to Circular Quay for the Bastille Festival for a huge celebration of French culture. Expect more food than you can eat, some of the best wine in the world, and special dining experiences including cheese igloos. 


To round off your Sydney weekend, jump onboard a food or bar tour with Local Sauce Tours. Venture through some of Surry Hills and Darlinghurst’s best bars as you hear stories of local heroes and villains and learn more about the general history. Plus, you’ll get to meet locals and other travellers. 


If you’re feeling like a night at the theatre, get dressed up and head to one of the theatres nearby. The Sydney Lyric Theatre, Theatre Royal, Capitol Theatre or even the Sydney Opera House will do the trick. If you’re looking for a before show dinner, you can’t go past the BLACK Bar and Grill for seafood and steak or Cucina Porto if you’re in the mood for Italian, both at The Star.  



Stay warm with a Local Sauce Tours bar hop


Prefer a low-key evening? Grab a spot right by the fire at The Duke of Clarence in the city. Inspired by an 18th-century London Tavern, this spot is bound to warm you up and is home to one of the best Sunday roasts in town. Or visit one of the many pubs around Pyrmont and warm up closer to your bed.



Our team of hosts would be delighted to assist with creating and booking a tailored itinerary of local activities for your trip. Get in touch with questions and requests, as well as other insider tips and suggestions on what to see and do in Sydney.


Please note, businesses and tour operators may have adjusted opening hours during special event periods and major holidays. Some activities require pre-booking and are subject to availability. It’s always best to check first!


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