Five Days in Sydney: Things To Do, Places to Eat & Drink

Sydney has been on my travel to-do list for as long as I can remember and it was always going to feature prominently in my Australian itinerary. I had planned to spend five nights (four-and-a-half days) in the city, but Qantas had other ideas. They cancelled my flight to Auckland on Monday morning and rebooked me on a much later one. Although I wasn’t exactly unhappy to have more time in Sydney, it was unfortunate that I then lost half a day from my much briefer stay in Auckland.

I spent three nights staying with some very good friends of mine who have lived in Sydney for several years and who acted as excellent tour guides — conducting me to all of the best food and (especially) coffee the city has to offer. For my first two nights, I stayed at the Sydney Harbour YHA in the Rocks. My private en suite room was the most expensive of my entire trip and, although large and clean, was pretty basic. However, I could see the Sydney Opera House from my window (if I stood on tiptoes; I'm short) and the view from the rooftop was even more impressive. Its location in the historic Rocks neighbourhood was good too, particularly for the central attractions around Sydney Harbour and Circular Quay, although like many parts of central Sydney, it is pretty hilly and has plenty of small passageways and unexpected staircases.

Things to do
As will soon become apparent — and goes without saying for regular readers — I spent a lot of time in Sydney visiting speciality coffee shops and enjoying Sydney’s culinary delights. I will be producing a separate post about the coffee, and you can scroll on down to see where I ate and drank other things. Here’s what else I got up to while I was in town.

Sydney Harbour and the Harbour Bridge
I took the airport train into Circular Quay, the not quite circular quay that serves as a launchpad for many of the city’s ferry services and that offers the closest views of the Sydney Harbour Bridge and Sydney Opera House. It was pouring with rain but by the time I’d checked into my lodgings and headed back out, the rain had stopped and a glorious sunset was in progress. I took dozens of photos of the bridge, the Opera House and the harbour, roping an unsuspecting local into taking a photo of me leaping.

You can walk across the bridge (indeed, I ran across one morning) and scale the southeastern Pylon Lookout for wonderful views across the harbour, but I booked a ticket for BridgeClimb Sydney, a three-and-a-half-hour experience where you are kitted out, given a safety briefing and, as part of a group, allowed to climb up to the top of the bridge. This is expensive, particularly if you opt for one of the ‘dusk’ sessions as I did (I paid $363), but I wanted to treat myself. After agonising for a week over the weather, I booked a ticket for Thursday evening and then, of course, a massive thunderstorm was predicted to hit right in the middle of my climb. 

The climb wasn’t cancelled but the BridgeClimb folks allowed me to reschedule for Sunday (this entailed an additional $20 weekend charge) and I was so glad because the weather on Sunday was wonderful and the sunset was absolutely glorious. Note: you can’t take your phone or a camera and although you get one free printed group photo, if you want any more photos, you have to buy them. In a moment of weakness, I paid $25 for one additional photo of me, although the USB stick also included a ‘free’ 8-second video they took of me. Finally, you also get a free ticket to go up to the top of the Pylon Lookout (‘where you can take as many photos as you want’), so if you’re planning to do that too, wait until after your bridge climb. Was the whole thing worth $383? I would say yes, but we were really lucky with the weather and sunset; I may have been more sceptical had it been a grey, rainy night.

Manly
A few miles to the northeast of central Sydney, the small town of Manly is an easy ferry ride from Circular Quay. The ferry ride itself (and you can take one of the iconic yellow and green ferries, which take 30 minutes and cost $7.10 (you can use the Opal card that also works on buses and trains), or a Manly Fast Ferry, which cost $8.70 and take 20 minutes) is part of the fun as you get fantastic views of Sydney’s eastern harbour. Try to sit at the front of the boat (on the right on your way out and left on the way back, for the best Opera House views).

In Manly, you can stroll to the main beach or to Shelly Beach (keep an eye out for little penguins on the rocks), where you can surf, swim or sunbathe. I got takeaway fish and chips from The Boathouse, which I ate on the beach. I didn’t swim because my kit was in the wash, but I did follow the Manly Clifftop Walk, a beautiful ramble up and over the clifftops overlooking the sea and the city. I ended up going all the way to North Head, which took me a couple of hours, and then took the shorter (40-minute) but less scenic road back to the harbour.

Bondi Beach
I’d planned to go to Bondi Beach on a weekday when I thought it might be quieter but neither Thursday nor Friday had suitable beach weather, so I caught the bus over on Saturday afternoon (both the 333 and the 380 take about 35 minutes from the CBD). Although it wasn’t hot by Sydney standards, it was warm enough to sunbathe and take a dip. The waves were pretty huge, though, so it was better suited to body-surfing and wave-jumping than swimming. The Qantas cock-up that left me with an extra day in Sydney on Monday, happened to occur on an extremely hot day — the mercury hit 36C in the afternoon — and so I headed back to Bondi to try to cool off. The sea was a bit calmer and I also visited the Bondi Icebergs Ocean Pool to do some proper swimming.

From Bondi, you can follow a four-mile walk along the coastal path south to Coogee Beach via several other beaches. It’s a stunning piece of the coast and if you get too hot along the way, you can always cool off in the sea. At the moment, an annual art exhibition called Sculpture by the Sea is in progress, which means you can see dozens of interesting art works while you walk.

Australian Museum
I didn’t manage to fit in a walking tour but I enjoyed my visit to the interesting and well-organised Australian Museum. The focus is on Australian natural history and anthropology, and there are some fascinating exhibitions on Australia’s first people and its diverse flora and fauna. The Australian Geographic Nature Photographer of the Year exhibition was taking place too, and there were dozens of stunning photographs that made me want to explore even more of this beautiful country.

White Rabbit Gallery
The White Rabbit Gallery has been described as one of the world’s best collections of contemporary Chinese art. There were some varied and thought-provoking pieces on display, from a ‘bondage cathedral’ (!) to video work. We spent an hour or so wandering through the well-curated rooms.

Food and drink
As I mentioned before, I created a separate speciality coffee post, but I’ve included below coffee shops and cafés where I also had particularly good breakfast and/or brunch.

Cafes
Rising Sun Workshop (Newtown) — excellent ramen in a motorbike workshop.

Reuben Hills (Surry Hills) — superb coffee and kickin’, Latin-influenced all-day food menu. I had a ‘broken omelette roll’, which was spicy, filling and delicious.

Haven: Tailoring Coffee Joyously (Surry Hills) — a stone’s throw from Central Station, this wonderfully named speciality coffee shop also tailors brunch dishes joyfully, adding an Asian — and often inventive — twist to classics. I had a creative take on an eggs Benedict, but my friend’s Amazing Kimcheese — egg waffles with kimchi, parmesan, sesame and vanilla ice cream — had to be tasted to be believed. It was actually delicious and strangely compelling.

Trafalgar St Espresso (Annandale) — the espresso (from The Little Marionette) is great here, but we came for the pies, which are from Black Star Pastry, one of Sydney’s best. My braised beef and beer pie was delicious.

Bourke Street Bakery (Surry Hills) — great for sweet treats, pies, sausage rolls and other baked goods.

Restaurants
Maybe Frank (Surry Hills) — I’d run out of planning momentum on my first evening in Sydney but luckily, I’d preloaded my Google Map with plenty of diverse eateries for precisely this reason. I settled on Neapolitan pizza and cocktail joint Maybe Frank, which was a 30-minute walk from Circular Quay. The pizza was very good and the cocktails — some Italian classics and some quirkier, like the Fish Outta Water that I tried — were also well-done.

BL Burgers (Darlinghurst and Parramatta) — on the way to Maybe Frank, I passed this burger bar and made a note to investigate further. As it happened, I returned just before heading back to the airport, and had their award-winning Blame Canada burger, an unabashed, maple-bacon and poutine-filled construction that was as delicious as it was gluttonous.

Spice I Am (Surry Hills) — there’s usually a line at this popular, cash-only, BYOB Thai restaurant. Three of us shared three dishes — one (pork belly) extremely spicy, and the other two slightly less so — and everything tasted superb. It’s not a fancy place but the food is great.

Acme (Rushcutters Bay) — Italian-influenced starters and delicious, creative pastas are the order of the day at Acme. After a few meaty starters, we ordered three pastas between the three of us: one with roast garlic and burned chilli, one with pumpkin and coffee, and one with black squid-ink and prawns. Each dish was immaculately prepared and the restaurant is cool but relaxed.

Automata (Chippendale) — if you’re struggling with decision fatigue, a tasting menu can be your saviour. I had no regrets with any of the five delicious courses at Automata. There’s a Japanese influence in the cuisine but the theme is really just simple but perfectly paired and prepared food. The minimalist décor and super service make this a lovely place for a special meal.

Bars
Gin Lane (Chippendale) — we popped down Gin Lane for a cocktail before heading to dinner at Automata across the street. Although the music was a little out of place, the cocktails were good and my cucumber, rose and gin drink came served in a snow globe. Because why not?

Bulletin Place (CBD) — tucked away on an upper floor on bustling Bulletin Place, this titular cocktail bar has a regularly evolving menu of cocktails in general and martinis in particular. Our drinks were well made and it’s a small and fun but still intimate spot.

Love, Tilly Devine (Darlinghurst) — cosy wine bar with excellent snacks and sharing platters.

Shopping
I didn’t end up doing a lot of shopping in Sydney, although had a few gifts to buy. The stretch of Oxford Street that runs from Paddington to Darlinghurst and Surry Hills, and some of surrounding streets, had the best range of independent shops and boutiques. Workshop Makery is a good bet for locally produced and themed gifts.

There are also a few design stores on George Street in the Rocks, like Shab & Shadi. Most of the big Australian and international brands and chains can be found in the CBD, in and around George, Pitt, Castlereagh and Elizabeth Streets. There’s a big Westfield Mall, although the Strand Arcade and Queen Victoria Building offer a more historic and visually appealing shopping environment.

One afternoon, we also headed down to Precinct 75, a collection of warehouses in St Peters selling, well, their wares — there’s a particular focus on homewares and interiors. If you’re in need of refreshments after your shopping, there’s a branch of Sample Coffee Roasters within the complex.