Bondi
I live here, like every other New Zealander in Sydney. My favourite things to do include going to the Bondi Markets (second hand clothes mostly) which are on every Sunday.
There's also a great Italian place called north bondi italian food (below North Bondi RSL, north end of Bondi Beach) which has a beautiful view of the beach. I recommend the 'Crab in a Bag', it's delicious.
The shopping on Gould street can be good, albeit very Bondi – stores like Tuchuzy and Grandma Takes A Trip are always full of pretty things. The Ksubi store is tucked along here as well.
It's also well worth going to the Cheap Monday shop off Hall Street, they have every colour and fabric of jeans (purple! pink acid wash! white velvet!) you can imagine and all are $80.
On Bondi Road are two really nice tapas/wine bars, one is called The Rum Diaries and one is called the Flying Squirrel, both are good, but I like the Rum Diaries better cause the barmen wear bowler hats and it's named after a Hunter S. Thompson book.
My favourite cafes are the organic shop on Gould Street for coffee and Gertrude and Alice which is a second hand bookshop/café for relaxing on a rainy Sunday.
Darlinghurst
Is a good place to go out for dinner. I like to go to Phamish: busy busy vietnamese – you'll have to wait for a table but it's worth it. It's cheap-ish and you can BYO wine. Yummiest dishes include the rice paper rolls, vietnamese omelette and the salt'n'pepper squid. I also like A Tavola, which is on Victoria Road - their handmade pasta is the best.
Also in this area is my favourite bar, Darlo Bar on Darlinghurst Road. It's upstairs at the The Darlo Pub. It's all decked out like a fifties Miami backyard, with astro turf and white painted wrought iron furniture and a flamingo! And you can get cheap beer, and they bring in any takeaways from a couple of restaurants near them. It's the only place you can smoke outside in the courtyard but still in the bar, which is a bonus if you are a filthy smoker like me (edit: no longer a filthy smoker). And, they screen movies on a Tuesday - I've seen Heathers, Blow Up, Blue Velvet and more.
Round the corner is a bar called the Victoria Tea Room, which is a major wank fest at night, but on Saturday and Sunday they do the best high tea. It's $35 a head but you get so much food. I'm obsessed with high tea. You need to book a week or so in advance though but it's really worth it. It's decorated in kind of British Raj style, so dark wood, lots of leather couches and potted palms and framed pictures, and then tea tables with white lace cloths and pretty china.
Paddington
Paddington has all the main chainstores and Australian designers – Willow, Sass and Bide, Ksubi. My favourite stores here are Incu (for imported stuff like Marc by Marc and Karen Walker as well as local designers including Lover). I also like Kit (a cosmetic store who stock Monoi, Jemma Kidd and other nice bits and pieces) and there are heaps of other cosmetic stores and fashion boutiques along here.
There aren't many cafes I like on Oxford Street itself, apart from The Sourdough Sisters and the Love Supreme. You have to go there for hot chocolate and something sweet, or for one of their amazing pizzas, or even just lunch. Yum. There's also a really cute café on William Street called Alimentari. It's a really small Italian deli with really good espresso and all eclectic.
William Street also has the Corner Store who stock Isabel Marant, Lover, Therese Rawthorne. And the London for a sneaky pizza and wine (good on a Saturday afternoon in the courtyard).
Also check out the Fringe Bar markets on Oxford Street on Saturday mornings, cheap jewellery and bags and clothes in the fringe bar which by night is a dark bar with sort of art deco fitout and chequered tile floor, chandeliers and red velvet. I have found all my jewellery here - a LOVE story style gold pendant, chain bracelets, a watch pendant, vintage sunglasses.
Surry Hills
Best pub here is the Cricketers – always busy and really good menu as well, cheap and delicious. Shopping around this area is awesome, so many vintage shops on Crown Street. Other cool shops include whendavidmetnicole for homewares stuff. Kawa is a nice café on Crown. Restaurantwise, I like Il Barretto for cheap and nice Italian.
Gallerywise, for emerging artists, Black and Blue and Somedays in Surry Hills are good. I also like going to the Museum of Contemporary Art in the Rocks, and the Gallery of NSW in the Domain.
If you like Chinese food, head to Chinatown (you think?). The best yum cha is at Marigold near the Haymarket, and if you like cheap dumplings/noodles there is a place called Din Tai Fan on the first floor of the World Square building on George Street. You have to get the soup dumpling (if you eat meat), it's amazing.
If you want to do any walks, the best one is Bondi to Bronte beach, take the ferry from Circular Quay over to Manly on the North Shore, there's a really pretty beach and lots of organic cafes.
Other good websites to check out for Sydney visits are:
www.twothousand.com.au
www.superfuture.com
www.fasterlouder.com.au
