I think the measure of a great city is one that changes slightly with each visit. Sydney passes that test with ease, offering previously undiscovered treasures as well as a fresh perspective on those classic views for anyone willing to head off the tourist trail.
Here are my top picks for cool things to do should you have a few days to spend in Sydney sometime soon.
Cockatoo Island
History geeks and ghost hunters alike will love exploring the bleak warehouses and creepy corners of Cockatoo Island. Sydney often feels like an extremely young city, but Cockatoo Island gives a rare glimpse of the desolate and deadly environment that would have greeted convicts arriving on her shores and the desperately harsh life they would have led.
A former convict prison camp turned ship building site, the island is dotted with colonial buildings and creepy WW2 tunnels. The best part is that you’re pretty much completely free to explore each building; walking around the old machinery and giving yourself the chills imagining all the lives lost over the years.
If history and ghosts don’t appeal to you, the island happens to host one of the coolest bars in Sydney, where you can sip rum cocktails on a sun-lounger with a great view of the harbour in the distance. So there’s always that.
Porteño
It’s probably fair to say Porteño is having a bit of a moment. Part traditional South American BBQ joint, part 50s cocktail lounge, Porteño has the good fortune to be set around a beautiful indoor courtyard with a nostalgic, Mexican vibe. Plus the perfectly-quiffed rock-a-billy staff bring just enough retro-cool without being kitsch.
Despite a long wait for a table when me and Alex went, we were happy to decamp to the bar upstairs, which serves a pretty decent whisky sour. From what I remember after drinking a fair few, the food was pretty good too. Luckily they sent us home with a doggy bag, as by that stage I wasn’t too much help at getting through the BBQ lamb and pork my husband ordered.
The Grounds at Alexandria
My favourite kind of places happen to be those that mix great architecture, design and foodie treats, so The Grounds at Alexandria is always on my list of favourite hang-outs. The kitchen garden and cute market stalls provide a great distraction while you’re waiting for a table in the converted former pie-factory inside.
Coffee lovers come here for the speciality roasts and space-age machinery but the food refuses to be overshadowed, with beautiful organic breakfasts and an incredible array of freshly baked breads, cakes and pastries.
Bronte and Manly Beaches
You can’t visit Sydney and not hit the beach. Although not particularly visually appealing, I’ve always found the surf at Manly to be even and reliable and you can rent boards right off the beach. Meanwhile Bronte is one of the city’s most beautiful beaches and also has pretty sweet waves. If surf hopping isn’t your style, why not try Paddle Boarding at Rose Bay instead?
Honorary mentions:
I also love stuffing my face at Black Star Pastry and Belljar Coffee (both Newtown) and Adriano Zumbo’s cafes.
Natalie Lasance 
Great round up – agree with all your picks. The Grounds is my favourite weekend haunt – just have to get there SUPER early! If you’re around in November the Sculpture by the Sea exhibition along Bronte-Bondi is also fantastic.
Thanks! I’ll definitely try and catch Sculpture by the Sea – sounds great!
Great post. Will def have to check out Cockatoo Island and Alexandria.