Sydney is the first stop for most travellers when they come to Australia, yet despite growing up not far north, in Brisbane, I felt like I hardly knew the city. I’ve visited on a childhood trip with my family, a few work trips and a couple of weekenders, but felt like I was missing what made Sydney so special.

Since I moved from Brisbane to Melbourne, my oldest friend, Chloe, has visited me every year. This year, we decided to meet in the middle instead, during a weekend girls trip to Sydney.

Apart from catching up with my oldest friend, I had another ulterior motive – sussing out Sydney as a potential destination to move to one day. My boyfriend would love to move there one day, but so far I wasn’t sold. This time, I tried to keep an open mind.

Read more: Sydney Travel Guide

We stayed in a gorgeous Air BnB in Bondi, a short walk from the famous Bondi Beach. Bondi is one of the most famous and beautiful beaches in Australia, so I was prepared to be underwhelmed – instead, I found myself checking realestate.com.au and mentally justifying the extreme cost of living in the dreamy beach neighbourhood.

Bondi is not well-connected by public transport, so if you’re planning on sightseeing all over Sydney, I’d recommend staying in Surry Hills, the city (although it’s not my favourite area) or Coogee, which is a beach suburb farther south of Bondi with better public transport options.

Darling Harbour & the Sydney CBD

Sydney’s spectacular setting on Darling Harbour makes the city famous, and it’s an essential sight while you’re in town. It was Chloe’s first time in Sydney, so we made the requisite trip down to Circular Quay to see the Opera House and the Sydney Harbour Bridge.

It’s the most famous part of Sydney, but personally I find Circular Quay soulless. We walked up to The Rocks, which is the oldest part of Sydney and is just near the Harbour Bridge. The rain had washed out the regular markets, so we headed back down to Circular Quay and made our way past the Opera House and through the Botanic Gardens, to the Art Gallery of New South Wales.

The Art Gallery of New South Wales has collections of Australian, European and Asian Art. It’s housed in the Vernon Building, which was designed as a classical temple to art and is comprised of several courts, flooded with natural light.

We didn’t stay for long, which in my experience, is the best way to enjoy an art gallery. We wandered past Victorian landscapes and European watercolours, which were surprisingly mesmerising.

My favourite was the dramatic Milford Sound, New Zealand by Eugene von Guerard. It was a pleasant surprise to stumble across William Henry Margetson’s The Sea Hath Its Pearls (1897) in the flesh, after growing up underneath it in my parents living room (or, a print of it, anyway).

I surprised myself, when I immediately recognised a painting, Cymon & Iphigenia as the work of Frederic Leighton, whose magnificent Flaming June was on display at The Frick in New York, last time I was there. I’m hardly an art expert – Flaming June is such a vibrant artwork that I think it’s burned into my brain, and there are echoes of it in his works in Sydney.

By the time we left, we’d worked up an appetite so we made a beeline for Bungalow 8 on King Street Wharf. We went via leafy Hyde Park and the very pretty St James train station, which feels like it’s stuck in a beautiful, art deco time warp. If only all train stations could look this good!

Bungalow 8 is an iconic Sydney bar and restaurant, overlooking Darling Harbour from King St Wharf. It’s a much better option that some of the over priced touristy restaurants in Circular Quay, and the al fresco seating by the water is the perfect place to enjoy a lazy lunch in Sydney. I had the calamari salad, and we shared some vegetarian rice paper rolls, a side of greens and a seriously more-ish strawberry cocktail jug. Perfection!

After lunch, we headed back to the Air BnB for our usual afternoon snooze – an essential part of our travel routine, wherever we go.

Bondi

We decided to stay local, in Bondi, for dinner. I had so many great recommendations from friends on where to eat and drink, as well as a handy guide from our in-the-know Air BnB hosts. It was so hard to decide where to eat, there were so many great options!

We chose Bondi Hardware, which is a cool little bar on one of Bondi’s main restaurant strips, Hall Street. It was buzzing, and we were lucky to nab two spots at the bar. The food and service was excellent, we shared kingfish ceviche tacos, a side of fresh spring asparagus and what looks to be a mushroom (or some sort of vegetarian) pizza – my photos and now memory are both a little blurry. I highly recommend Bondi Hardware and would definitely return next time I’m in Bondi.

Our weekend in Sydney was at the whims of very unpredictable weather, and when we woke up the next morning it was very glum and rainy. We walked down to the famous Bondi Beach for the first time, which was a ghost town under grey skies. Fortunately, the Bondi Beach Graffiti Wall is colourful no matter what the weather, so we strolled along the waterfront admiring the art before breakfast.

On a recommendation of a former Sydneysider, we had breakfast at The Nine, a tiny hole-in-the-wall café with a menu that rivals cafes at least three times its size. I had a serious case of menu decision paralysis, because everything looked so good! I went with a breakfast bowl filled with vegetables, kale, a poached egg and beetroot hummus, which was delicious. I have to admit, I much preferred The Nine, to the famous Bill’s, which is the café of Australian chef Bill Granger, which has three outposts in Sydney, as well as London, Tokyo, Honolulu and Seoul. The service and ambience at Bill’s was lovely, but I found the menu to be a very classic version of brunch – Bill’s led the way in creating “Sydney food”, but these days I prefer cafes with more creative menu options.

Since it was raining when we finished brunch, we decided to wait it out while getting our nails done. We went to Bondi Nails, which has seriously mixed Google reviews, but I found completely up to my germ-phobic standards. They had SNS colours my regular salon in Melbourne doesn’t have, cue holiday nails!

Watson’s Bay

You can waste an entire holiday waiting for the weather to clear, so we decided to Uber down to Watson’s Bay anyway and hope for the best. Despite the gloomy weather, Watson’s Bay Boutique Hotel was still packed. We nabbed a waterfront table on the deck, overlooking the beach – something I’m sure that would have been impossible in better weather.

Watson’s Bay, like most inner city Sydney beach suburbs, is eye-wateringly expensive – so I had to try very hard not to envision a life in Sydney as living in Watson’s Bay. The median house price in Sydney is 1.15 million – in Watson’s Bay, it’s 3.8 million.

I had the smoked mackeral bruschetta with pickled celery, shaved fennel and radish which was the perfect light lunch, washed down with a frose. Again, another winning spot to eat in Sydney – 100% would return.

I tried not to let a suburb I would never live in influence my opinions on moving to Sydney, but it was pretty hard when we stumbled across The Gap lookout, not far from the hotel. From one side, the view looked over crumbling cliffs and a wild ocean, and from the other, the view was across Watson’s Bay to Sydney’s CBD, with views of the Harbour Bridge.

Surry Hills

We spent Saturday night in Surry Hills, one of Sydney’s most popular neighbourhoods for bars and restaurants. We made the mistake of not booking a table at The Winery, a Surry Hills institution that was jammed on a Saturday night. We waited for a table in the enchanting wine garden (enchanting is literally the only word for it), and were seated for dinner upstairs in the charming Champagne Room. We shared the buffalo ricotta with country bread and some arancini, and I had the watermelon and feta salad – my favourite! Naturally, the meal was matched with Champagne from the venue’s extensive Champagne list.

We finished dinner quite late, at around 10:30, and headed to The Dolphin Hotel (a bar, not a hotel, for non-Aussie readers), but we only had time for one glass of wine before we had a run in with Sydney’s infamous lockout laws. It was really strange seeing security guards empty a pub at midnight, when no one in the crowd was rowdy. We must have looked particularly confused, because one of the security guards started chatting with us, and recommended heading to the nearby Beresford Hotel, which for some reason, wasn’t required to close at midnight. We nearly didn’t go in, because from the outside, the ground level bar looks like a scummy pub, but when we entered we found stairs to club on the top level. I decided at the ripe old age of 24, that my clubbing days are pretty much over (unless it’s somewhere genuinely impressive…ie. probably not in Australia).

We spent just over an hour there, before the lockout laws took effect there at 1:30am. Rather than schlepping across town to find a venue which was still open (Sydney’s lock out laws are not only patronising, they’re also messy), we called it a night and went to bed. Touche, NSW government.

The Grounds of Alexandria

Inconveniently located in Alexandria, visiting The Grounds of Alexandria was an expensive Uber expedition. It was worth it, because it was easily the top brunch experience of my over-brunched existence. The Grounds of Alexandria is a whimsical precinct in the grounds of a former pie factory, featuring a cafe, markets and a garden. It is like Disneyland for Instagrammers. I wish we’d booked in advance – we waited nearly an hour to get a table for breakfast.

Hot tip: You actually don’t need to line up for a table if you want to eat at the outdoor tables. You won’t have tables service, but they’re the best seats in the house.

Newtown

Since we were already halfway across town, we decided to push on and check OUT Newtown. Newtown is what Melbourne’s Brunswick and Brooklyn’s Williamsburg once were, pre-gentrification. Arguably, Newtown is also gentrifying, as everywhere in Sydney feels expensive, but it was definitely still firmly outside the “Bondi bubble.”

We didn’t know where to go, and just asked for our driver to drop us off at King Street. We were armed with a few recommendations of places to eat, like The Continental and Stinking Bishops cheese shop, but as we’d come straight from brunch we weren’t hungry. We wandered up and down King Street, and saw a bit of street art, but apart from that didn’t really know what to do. Neither of us were in the mood for op-shopping, so we wandered aimlessly for a while. We stumble across Black Star Pastry, which is the pastry on every foodie’s lips (figuratively and literally) at the moment. I couldn’t not try their claim to fame, the Strawberry & Watermelon Cake, so bought a slice to take home for later. It completely lived up to the hype, and I think this might be what dreams taste like.

Sadly for Chloe, that evening when we went to eat our prized pastries, she realised they’d given her the wrong pastry, which tasted a little like soap if I’m being honest.

I’m never going to do the maths on how much we spent on Ubers on this day, because I have a rough figure and it makes me a little bit sick. The plan was to PT back from Newtown, but due to trains being down and bla bla bla it would have taken over an hour to get back to Bondi.

Sydney’s public transport is pretty terrible, and it’s something that makes me think twice about living there. I love living in a pedestrian and PT-friendly city like Melbourne, and don’t know whether I could go back to buses, cars and sitting in traffic.

Then again, I could really get used to the sunshine, warm weather and the lifestyle that comes with it.

Bondi

We had lunch at The Bucket List in Bondi, which was full to the gills in the warm weather. I sweated my way through a fish burger (in hindsight, a terrible choice in the heat) and then we retired to our Air BnB as per usual.

Another Bondi winner for dinner – a pintxos bar, CanCava. We had a light dinner, sharing bruschetta, a pear & honey dish and guacamole and tortilla chips. 100% would eat here again.

The Bondi to Coogee Coastal Walk, backwards

It was raining again on our final day in Sydney, but we were determined to do the Bondi to Coogee Coastal Walk. Back in 2013, when we travelled through Europe together, we took the trains between the towns of Cinque Terre and planned to do one hike, between the towns of Manarola and Riomaggiore on the last day. Had we planned it a little more enthusiastically,we would have known that that particular trail was closed during our visit. Instead, as we realised the on our last day in Cinque Terre, we shrugged our shoulders and shirked any physical activity. It is one of my few travel regrets and I was determined not to flake out this time!

The coastal walk runs through the beaches of Coogee, Bronte, Tamarama and Bondi and is an easy 4 kilometre (2.5mile) walk.

We started with breakfast at Porch & Parlour in Bondi, which was absolutely packed on a rainy Monday morning – definitely a good sign! We were not disappointed, the food was delicious and the perfect start to an active morning.

So that we’d end the walk in Bondi, we caught an uber to the other end in Coogee, and did the trail backwards. By the time we reached Bondi around midday, it was a beautiful day! I’ll do another post with more photos from the Bondi to Coogee, stay tuned.

Once back in Bondi, we saw the famous Icebergs sea baths, which are set on the cliff edge, semi-submerged in the oceans. We decided we were too underdressed to eat at Icebergs’ bar, so we returned to The Bucket List for fish tacos, to wrap up the trip.

   

For the first time, on this trip I could see the real appeal of living in Sydney, but also came head to head with the logistical nightmare that is catching public transport around the sprawling city. I’ve grown so used to living in a walkable, liveable city like Melbourne, although, as it’s been ranked as the Most Liveable City in the World for seven years running, I’ll need to make some adjustments no matter where I live next. Sydney’s sunshine and warm climate is a serious drawcard, and the possibility of living near a surf beach while still having access to big-city necessities (and work opportunities) is very appealing.

The jury is still out on living in Sydney, but as a weekend getaway it was a runaway success!

Have you been to Sydney? What’s your favourite thing to do there?

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