Autumn and Winter 7 Day Travel Plan


As the sunshine hours shrink to their lowest, the cold kicks in and Sydneysiders embrace the zest of the city day and night. Autumn and winter is blessed with sunrays and the weather rarely dropping below 10 degrees. The colder months although chilly, is charming with sunny clear days. Sydney is packed with a line-up of events, winter markets and the best dining experiences. The city is enchanted with lights, music and ideas as Vivid comes alive and Sydneysiders get in spirit to celebrate the rugby league season.


Monday glebepoint_02_1280x720A quaint inner-city suburb that emanates a small-town feel, Glebe has enchanted Sydney locals for years with its diverse restaurants, cafes, bars and boutiques that line Glebe’s main street. Nestled between the CBD and the beautiful Rozelle Bay, Glebe offers a plethora of things to do and sights to see for the wanderer. Be warned, the hourglass tends to shift a little faster than usual while in this bohemian paradise.

Who thought being spoilt for choice would be so difficult!? Glebe has a café on every street corner so an amazing coffee and perfectly poached eggs are always within arms-reach. Clipper Café should be high on your breakfast priority list; they’ve truly refined the art of the eggs benedict.

Do Tai Chi on the waters edge at Glebe’s Jubilee Park or take the scenic bay walk that wind around Rozelle and Blackwattle Bay. If vintage is your vice, Glebe is stocked with antique treasures and ageless threads at Junktique Emporium or St. Vincent’s de Paul.

Put down your shopping bags and pick up a well-deserved glass of wine at The Little Guy. While you nibble on the complimentary popcorn and sip on the local craft beer recommended by your bartender, mull over the abundance of restaurants and cuisines at your disposal. The Flying Fajita Sistas is a must if Mexican is your weakness or the Different Drummer for a spot of Tapas.


Tuesday   artgallery_02_1280x720While it’s usually packed on the weekends and afternoons, a Tuesday morning trip to the Art Gallery of New South Wales means you can tranquilly stroll around the historical museum and observe beautiful archival and contemporary, local and international artworks.

Enjoy an afternoon of fine dining at MorSul restaurant located within the gallery. Owned by leading Australian chef Matt Moran, MorSul offers modern Australian cuisine and stunning views over the Botanical Gardens and Sydney Harbour.

Admire the Sydney city skyline as you cut across the sprawling green Domain, through bustling Circular Quay towards the Museum of Contemporary Art. Educational and engaging, the museum offers a wealth of diverse contemporary visual art for you to get lost in.

Walk through the narrow lane of Suez Canal and onto the traditional shops on George, Playfair and Argyle Street where you will find a blend of traditional art, crafts and classic patisseries.
Finish the day with dinner at Sake Restaurant for a mixed contemporary and traditional Japanese menu at The Rocks.


Wednesday chinatown_01_1280x720Capture the excitement of the lively culture, vibrant colours and flavourful Asian cuisine of Chinatown. Only a 5 minute walk from Town Hall or Central Station, you will recognise it from the blaring soundtracks of Cantopop and the bustling of people bargaining deals in small shops and Asian grocers.

Over the tramline is Sydney’s original marketplace – Paddy’s Markets. At 150 years old, there is something for everyone in this eccentric, buzzing hall filled with aisles and aisles of food, clothing, jewellery, homewares and more for you to wind your way around. You will not come out empty- handed!

Chat Thai is the place to go for an authentic Thai lunch in Haymarket. This Sydney favourite is a great meeting place to socialise and indulge in food developed from the streets of Thailand.

As you venture out of Chinatown, walk down George Street towards the Queen Victoria Building. The cathedral scale QVB is rich in history and characterised by Romanesque architecture. Recently undergoing a $48 million refurbishment, the QVB houses over 200 of the finest fashion, jewellery and homeware boutiques as well as splendid cafes and restaurants.

Make your way down Market Street to Darling Harbour, where you can enjoy the sunset with waterfront views at Nick’s Bar and Grill. Offering exquisite seafood as well as grilled meats and an amazing vegetarian selection, Nick’s is the perfect place to wind down your busy CBD day. For the young at heart, make sure to catch a 3D movie experience at the world famous IMAX theatre.


Thursday  newtown_11_1280x720Begin to wind down the week in Sydney’s most culturally diverse district, the Inner West. Centered on the long but vibrant King Street, Newtown is overflowing with unconventially cool bars, eateries, theatres, cocktail terraces, quirky bookstores and even quirkier people. Once you alight the train from Central, you will be greeted by a stark contrast to the sleek and modern Newtown Station: an array of confident buskers, incense, unique clothing and thought-provoking hairstyles.

Don’t miss out on a trip to Cream on King as you make your way down King Street. Like most of the shops in Newtown, this groovy little spot always blasts the best playlists as you splurge on unique finds and beautifully restored vintage threads. Warning: if you spot something you love, snatch it up because it will probably have gone by tomorrow!

Head back down Enmore Rd to Sadhana Kitchen, one of Sydney’s favourite vegan cafes. This wholesome joint uses organic produce to deliver some of the best raw vegan food in town. With all dishes prepared below 40 degrees, Sadhana ensures nutritional value in all meals whether dining in or ordering lunchbox delivery. If you aren’t hungry enough for the raw vegan BLT (with coconut bacon!), try the super feast smoothie: with cacao powder, raspberry, goji berries, almonds and shredded coconut.

Head back to Newtown for a cheeky Thursday afternoon pub-crawl. Grab a spot on the sunny balcony of Newtown Hotel for some good old-fashioned Newtown people watching while kicking back with a beer or tap wine (you heard right – wine on tap!). Visit old faithful Courthouse Hotel and finish off at Earls Juke Joint, a New Orlean’s inspired bar of the Shady Pines and Frankie’s variety. Or, if you’ve got tickets, catch a music or comedy show at the Enmore Theatre down the road.


Friday surryhills_06_1280x720There’s no other way to kick off the weekend than with a hearty breakfast. Bill’s in Darlinghurst is so good it’s expanded out of Sydney to Japan and the UK – now the world can enjoy Sydneysiders’ adored ricotta pancakes. If you’re up for something on the savoury side, tuck into zucchini fritters or the full Aussie breakfast.

Wander down to the Brett Whiteley Studio in Surry Hills for a unique glimpse at the former workplace of one of Australia’s most interesting artists. The studio offers an inside perspective of Whiteley’s sketchbook, where evidence of his tumultuous life is revealed in the pages.

Around the corner is the heart of Surry Hills, Crown Street. Although long, Crown Street is home to some of the best pubs, bars, cafes, organic grocers and shops. For the avid thrift shopper, indulge yourself in C’s Flashback or Cream on Crown (sister to Cream on King) or rummage through the wacky Mexican Day of the Dead- themed boutique, Holy Kitsch.

If your stroll through Surry Hills has left you a little empty, the best burger in Sydney is sure to pick you back up. That’s no exaggeration. After 6 short weeks of its re- opening on Albion Street, Chur Burger was indeed dubbed Sydney’s best burger joint by the Sydney Morning Herald. At only $10 a burger, Chur offers all your favourites, including a delicious veggie patty.

If you’re still running on yesterday’s vibe, start your TGIF night at Surry Hills’ answer to Earl’s Juke Joint, Tio’s Cerveceria– where there is owl paraphernalia and tequila aplenty. Boogie your way to the old school playlists of The Soda Factory on Wentworth Avenue.


Saturday paddingtonmarketsSaturdays in Paddington exude Sydney’s creative flare at the famous Paddington Markets. From hippies to vintage-wearing hipsters to families to artists and fashion gurus, these markets draw people from all walks of life to shop around over 150 stalls of handcrafted goodies. Soak up the tunes of local muso’s and purchase some fresh local bread for Saturday lunch as all funds go back into the community and its talent.

Still peckish? Grab some homemade ravioli at Italian-inspired deli café Alimentari. Spend your lazy Saturday afternoon admiring the old labyrinth-style streetscapes and rustic terrace houses of Paddington, one of the most historically recognised suburbs in Sydney’s East. For the optimal shopping experience, explore the wealth of handmade, readymade, recycled and retro retail that lines Oxford Street.

Enjoy a sunset dinner and drinks at the Walsh Bay waterfront of Sydney Dance Lounge before attending a spectacular show at Sydney Theatre Company or Sydney Dance Company – look out for famous faces!


Sunday centennialpark_13_1280x720Wind down at the end of the week with a cozy breakfast at Brown Sugar in Bondi. This romantic little gem provides homemade comfort food as well as relishes, jams, stocks and lemonade.

For the ultimate Sydney market experience, stroll around the coolest and funkiest stalls at Bondi Markets. Turning 20 this year, these markets have helped kicked off some of Australia’s best designers and is home to the best of Sydney’s mix of eclectic and laid back flair.

End the day at Centennial Park. Surrounded by statues, swaps and native Australian flora and fauna, these beautiful parklands are one of the simultaneously peaceful and productive places in Sydney. Escape the winter chill by having a picnic in the sun or hiring a bike to ride around and perhaps catch some of the equestrian horses trotting past.




St. Patricks Day  

St. Patricks Day in Australia is celebrated with vibrant street parades in the CBD, family and friends, Irish dancing, and an abundance of green attire. Grab a pint and join the fun.

When:17th March
Where: Family Day in Hyde Park; parade along George St, Park St, Elizabeth St and James St.
Contact: 0414 647 909


Sydney Royal Easter Show  

Sydney Royal Easter Show has a bit of everything from arts & culture, agriculture, free live entertainment and hundreds of food stalls and rides. There’s something for the whole family.

When: 26th March – 8th April
Where: 1 Showground Rd, Sydney Olympic Park
Contact: 9704 1000




BMW  Sydney Carnival  

Spanning 6 weeks through autumn as one of Sydney’s most prestigious sporting events, the BMW Sydney Carnival will bring the best in horseracing over two premier racecourses.

When: 4th April
Where: Rosehill Gardens and Royal Randwick, Rosehill 2142
Contact: 1300 729 668


Fashion Week

Once a year, Sydney hosts the premier Mercedes-Benz Fashion Week, an international fair representing the very best in fashion. Here leading, cutting-edge designers unleash their collections to an international audience.

When: 12th April – 16th April
Where: Carriageworks 245 Wilson St, Eveleigh


Sydney Comedy Festival  

Sydney Comedy Festival brings the funniest acts from Australian and international comedians. Previous guests have included Greg Fleet, Stephen K. Amos and Fiona O’loughlin.

When: 20th April – 12th May
Where: Various venues throughout Sydney




Sydney Writer’s Festival 

There will be over 300 events around Sydney that will tackle various topics and feature keynote talks from intellectuals and writers from around the world.

When: 18th May – 24th May
Where: Walsh Bay (Pier 4/5 and Sydney Theatre), Sydney Town hall, City Recital Hall, Sydney Opera House and The Mint
Contact: 9252 7729


Vivid Sydney  

Vivid Sydney features a mesmerising collection of public exhibition of outdoor lighting, sculptures and installations around the city and harbour.

When: 22nd May – 8th June
Where: Sydney City
Contact: 9931 1111




Sydney Film Festival 

Sydney Film Festival is a 12-day festival that screens feature films, docos, animations and short films from around the world in various venues across Sydney.

When: 3rd June – 14th June
Where: Various cinemas around Sydney and the City (visit for details)


State of Origin  

Rugby’s battle between the Blues and Maroons can be caught at ANZ stadium or Suncorp Stadium. If you can’t get tickets then be sure to catch it on TV.

When: June
Where: ANZ Stadium or Suncorp Stadium
Contact: 0412 298 124



Hit the street to enjoy musical performances during Katoomba’s Winter Magic Festival. Many Blue Mountains’ restaurants and hotels will offer special Yulefest packages in mood of the festivities.

When: June – August
Where: Blue Mountains




City to Surf Run  

The annual City2Surf is open to both competitive and non-competitive runners and will take runners through Sydney’s East to a finish at Bondi Beach.

When: 9th August
Where: Hyde Park to Bondi Beach


Sydney Design

Held in the Powerhouse Museum the Sydney Design brings together an exciting array of contemporary design, workshops, talks and exhibitions, drawn from across Sydney’s creative industries.

When: 16th August – 24th August
Where: 500 Harris Street, Powerhouse Museum, Ultimo
Contact: 02 9217 0111

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