The locals’ guide to Sydney

WT Writer
Feb 14, 2018
One of the world’s unmissable destinations, we get the lowdown on the Harbour City from three well-heeled locals



Caitlin Stewart, style icon and image consultant, shares her tasteful tips for where to see and be seen in the city.

Where’s the best spot for shopping?

Pitt Street Mall is a bustling metropolis with many high street and department stores and local and international brands. Nearby in Paddington, Glenmore Road and William Street offer high-end Australian boutique labels – my favourite is Di Nuovo. King Street in Newtown is great for vintage stores and unique designers, while Bondi Beach is the place to go to wander around beach-vibe boutiques.


Pitt Street Mall

What’s Sydney street-style like?

On the whole, it’s fairly casual thanks to our relaxed lifestyle: we love our sneakers and distressed denim. That said, the style varies depending on the suburb. The Inner East has an urban chic feel, the Inner West is a touch more ‘arty’ with a move toward sustainable and ethical fashion. Sydney city and the north shore tend to be more refined with a preppy feel. Closer to the beach suburbs like Bondi, things are more casual: short shorts in summer, oversized knits in the cooler season.

What’s a stylish way to spend an evening?

One of my favourite places to bring visitors is Café Sydney, in the old Customs House precinct. Afternoon drinks at Opera Bar, just below Sydney Opera House or Blu Bar on 36 at the top of the Shangri-La Hotel are also good picks.

What’s a good souvenir to bring home?

As a stylist, I’d suggest a beautiful piece of jewellery from an Australian designer like Samantha Wills, Amber Sceats or Jan Logan. If jewels aren’t your thing, get an original print from an Aussie artist: find these in some of the little art galleries in the Eastern suburbs and the Inner West.

Tell us something about the city that only the locals know?

A tip for coffee lovers: some of the best brews around town are tucked away in unlikely spots, so do your research before going for your morning caffeine hit.


Jay Santiago ,a Sydney based food blogger, is always on the hunt for her next ‘eatventure’. She lifts the lid  on where to go for the city’s best bites.

What’s your go-to restaurant?

At Sokyo, head chef Chase Kojima is incredible. Taking the high quality and balanced taste of Japanese cuisine, he gives it a classic Sydney twist. Using the best in-season ingredients, he intertwines the two cultures and I’ve never had anything less than a 10 out of 10 dining experience there.

What’s trending food-wise?

It’s the ‘year of the poke’ in Sydney at the moment and you can find this Hawaiian-inspired sashimi bowl popping up across the city.

The must-try local food?

The best thing about Sydney is how diverse the culture is, so it all depends on where you find yourself. That said, I would absolutely recommend an early morning visit to the Sydney Seafood Market.


Dining at Sydney Seafood Market

What’s the city’s most stylish restaurant?

Both Quay and Bennelong – handily located directly opposite one another – are among the most stylish eateries. Both offer great food and fantastic views.

What’s the city’s best-kept foodie secret?

Seek out the underground bars, which are not only great for drinks and that speakeasy vibe, but have surprisingly smashing food too.


Justine Simpson, operations manager at I’m Free – a company specialising in local walking tours of Sydney’s cultural highlights – knows the city better than most.

On a stopover, what are the must-do’s?

Number one would have to be the Manly Ferry. From Circular Quay head over to Manly. On the way you’ll see the CBD, Sydney Opera House and the Botanic Gardens disappear as you head toward the picturesque seaside town. Back on dry land, walk through the historical Rocks district to the opera house for lunch. Next, take the 333 all the way out to Bondi where you can set off on a hike to Coogee. An amazing 90-minute walk packed with scenic vistas; keep an eye out for humpback whales migrating off the coast. Catch the bus back into the city and hop off at Oxford Street then head to Surry Hills for great local food.

What’s the most exciting cultural aspect?

There’s a whole range of people that call Sydney home and we’re very proud of this and our diverse culture, especially when it comes to food. We’ve got a great range of local produce and an experimental attitude with everything from delicious vegan pizza to mac and cheese waffles on offer.

The best area for exploring?

That’s a tough one. There’s something for everyone and it depends on your likes.

Walking from the Opera House through the Botanic Gardens toward Potts Point and Darlinghurst, then finishing up in Surry Hills will give you a good taste of the city.

Any hidden cultural gems?

Newtown. Rough around the edges but soft and gooey on the inside, it’s where the majority of the city’s students reside and is filled with street art, buskers in gold leotards and street performers strumming air guitars. It’s also home to some great vegan restaurants – try Gigis; countless Thai eateries; and some famous bakeries such as Black Star Pastry and Cow and Moon. There’s also great shops, rooftop hangouts and the famous Enmore theatre.

Tell us something about Sydney that only the locals know.

We call ourselves Sydneysiders, we don’t do Starbucks as we have a booming local coffee culture and our favourite breakfast food is a black tar-looking yeast extract that you may know as Vegemite. Oh, and you can try Kangaroo or emu pizzas at The Australian Hotel.