Two Days In Sydney: The Perfect (Grown-Ups) Weekend Itinerary

I’ve always had a love-hate relationship with Sydney. Yes, its beauty is unquestionable. But, being from a city a quarter of the size, I’ve always found its vibe too busy, and somewhat unfriendly. However, it’s been years since I really had the opportunity to explore Sydney for more than a few hours, and in that time I’ve grown. Experiencing some of the busiest cities on earth made me appreciate this sunny seaside metropolis with new enthusiasm. I had a blast. (Side note, we encountered so many friendly locals – a complete 180 from my previous experiences!)

Note: this post contains affiliate links. If you click through and make a booking, I earn a small commission at no cost to you.

Mr. W and I travelled to Sydney this past weekend to celebrate our wedding anniversary. That’s right – for 48 blissful hours it was Parents Gone Wild. We really needed this opportunity to reconnect after a busy couple of years… Next year we will welcome a full-time international student into our home and I will commence writing my thesis. Yep, this weekend was definitely what we needed – a glimpse of relative peace (or depending how you look at it, the eye of the storm).

We flew into Sydney on Friday night and stayed at the lovely Swissôtel on Market Street (near Pitt Street Mall). We caught the train in from the airport, checked in, and ordered some delightful room service. The next day, we were ready for Sydney action.

I’m quite proud of this little itinerary in that I think most things went off without a hitch. There’s nothing I’d really do differently.That means I can recommend you follow this itinerary without making anychanges. Easy!

Breakfast at Circular Quay

I think Circular Quay needs to be first on the list. I mean, to the left is the bridge, to the right is the Opera House, so no matter where you look there’s no doubt you’re in Sydney. It’s the point that orients you to the rest of the city. You don’t go to Paris and save the Eiffel Tower for the last day.

On the Western side of the Quay is the Museum of Contemporary Art (MCA) and out the front is their restaurant, Graze. An absolutely beautiful spot for breakfast. I ordered the eggs Florentine and Mr. W ordered the corn waffles, and we ate and chatted while we watched the ferries come and go from the Quay. The Royal Caribbean Explorer of the Seas was in port and we marvelled at its size as it sat right in front of us.

Shout out to the friendly lady at the table behind us who,completely unprompted, jumped in and took this photo for us.

Circular Quay lookout

Above the Circular Quay train station is the Cahill Expressway. If you walk over to the Eastern side of the Quay, there’s an elevator that will take you up onto the footpath next to the road. It’s here you’ll find the best view of the whole Quay. We actually set our tripod up here to get some good footage. If photography isn’t your thing no worries, but it’s something we’re trying to get better at so finding this spot was fantastic.

(Shout out to the friendly Scout leader who saw us setting up at the train station and told us about it.)

Take the Ferry to Manly

I wanted to take the traditional green and yellow ferry to Manly, but I also didn’t want to wait half an hour. The Fast Ferry was about to depart so we said “stuff it!” and bought a ticket… Only to find out 30 seconds later we could have used our Opal cards. So hot tip: the Fast Ferry is still public transport, and it still accepts your public transport card.

The journey takes 18 minutes as opposed to the 35 or so minutes on the regular ferry. I also found it a bit smoother… and there’s a licenced bar onboard!

Whichever option you choose, the journey is worth it. The views of the harbour, Kirribilli (where the Prime Minister lives) and many gorgeous little coves are unparalleled. Taking the ferry is a must just to get these views.

When you hop off the ferry you’ll hit Manly Cove/Cabbage Tree Bay. The water here is crystal clear and it’s nice and sheltered… the perfect spot for some standup paddleboarding or a more relaxing dip. 

While Manly is one of my absolute favourites, check out this guide to the best Sydney beaches.

Eat lunch in Manly

Manly is full of great lunch options.

Back in 2007, I visited one of my girlfriends who was living in Sydney (shout out to V by the way, who just got engaged!). She introduced me to the Manly Wharf Hotel and I have been obsessed for the past 11 years. Look, I’m sure there’s better pubs in the world, but who can say no to enjoying that view with a nice cold beer? You can actually watch the fish swim under you as you drink. The Manly Wharf Hotel has an excellent menu of the fancypants-pub-food persuasion and drink options to match.

Also on the Wharf is Queen Chow, a modern Cantonese restaurant. The vibe inside is super chic and again, if you sit by the window, the view is lovely.

Walking down The Corso there are a bunch of chain eateries and cool pubs. Alternatively, you’ll find a couple of cool Asian eateries on Wentworth Street and a delightful little Greek place (Terracotta Ouzeria) on Victoria Parade.

We also walked through a delightful little Christmas market and managed to pick up some gifts for the family. 

Manly to Shelley Beach walk

At the end of The Corso/Wentworth Street/Victoria Parade, you’ll find Manly Beach. It was super windy in Sydney last weekend and as a result, Manly Beach was really choppy (as opposed to Manly Cove on the other side by the Wharf, which was glorious). The beach was packed but people could only swim in a small patch due to waves crashing onto rocks on one side and a huge riptide on the other. Instead, there’s a lovely walkway that takes you ten minutes up the beach to Shelley Beach, a delightfully protected cove. The contrast was amazing: within view, we could see both surfers trying to avoid rocks at Manly, and snorkellers and paddleboarders in glassy water at Shelley. While both were packed, Shelley is my pick hands down (though be warned, eat first!)

Opera Bar

Okay, you want something full-on? Try Opera Bar at sunset on a Saturday when there’s a Bon Jovi concert in town. When you get off the ferry the Opera Bar is right there (you know, by the Opera House) but I elected to go back to the hotel and change first.

The Opera Bar serves snacks and meals, and the Opera Kitchen is a restaurant in the same complex. But knowing where we wanted to head for dinner we figured we’d just stop for a drink. It was beautiful watching the Royal Caribbean ship depart into the sunset while I sipped on a “Free to Rome” cocktail.

While there isn’t really any dance space, the DJ was fantastic (she was actually singing while spinning) and some days live bands play too. Let’s be honest though… when planning this itinerary I wanted so badly to find somewhere to go dancing, but that was a hard pass from Mr. W.

Hacienda Bar

Still on the Opera side of the Quay is Hacienda Bar, in the Pullman Quay Grand complex.

There were a couple of hens parties happening when we were there… Which is totally understandable as the décor is perfect for a hens!

Be warned, this place isn’t cheap (is anywhere in Sydney, especially on the Quay?). But the drinks were super fancy and the Cuban-inspired sharing plates were delicious. For drinks, I highly recommend the whiskey sours and anything on the tiki menu. Food-wise, we ordered the prawn skewers, arancini, tuna ceviche (anyone who reads this blog knows how much I adore ceviche), pumpkin flowers and hot wings. I could have kept eating and eating and eating, honestly. But just like that, we’d blown $300.

Walk through The Rocks

Were fast-forwarding to Sunday morning here because who knows what happened after Hacienda Bar (for you, if you’re following this itinerary… my memory is fine, thank you).

So, The Rocks is this beautiful corner of Sydney between the CBD and the Harbour Bridge. It’s the old part of town where you’ll find traditional colonial buildings, old pubs, and quaint little cafes and shops. You could really walk through here at any time but we thought we might try and find a cool spot for breakfast. Instead, we got distracted by the cook Sunday market that was happening and the next thing we knew, we’d walked away from the action. So, we kept walking around the coastline to Walsh Bay.

Breakfast at Walsh Bay

Walsh Bay is complete surprise. I never really knew it existed other than as the name of a seaside suburb mentioned on Water Rats (don’t worry about that 90s Australian pop-culture reference). Anyway, it’s a little enclave to the west of The Rocks that’s currently undergoing a bit of a spruce-up. Old docks are becoming trendy apartments and lovely eateries and bars line the waterfront. 

We ate breakfast at a Mediterranean cafe called Lavana. Ummm…. soooo good. We ordered the saucy eggs (I’m an absolute sucker for this dish anywhere) and the Middle Eastern breakfast. Think: a big breakfast but with olives, pita, and lamb sausages.

Walk through Barangaroo and Darling Harbour

I’ll admit I needed to walk off breakfast. Just like I had needed to walk off every single other Sydney meal! So we kept walking along the western shoreline from Walsh Bay down to Barangaroo. This is where the new Crown towers are being built to much controversy. And I could go on for days about all that, probably, but I will say… for all its modern soullessness, it’s certainly physically impressive. 

Keep walking, and Barangaroo will eventually turn into Darling Harbour. I loved just strolling along here, but I wanted to go into every single eatery. So if you feel like another coffee, or more breakfast, or brunch… here’s the spot to stop and recharge again. 

In Darling Harbour, there’s the aquarium and the maritime museum if either option appeals to you. We had a lunch reservation to make so we didn’t bother, but if we had the kids we’d definitely go to the aquarium. Of course, fish enthusiast Mr. W. insisted we go but we ran out of time (conveniently). Full disclosure: I’ve been twice before and it’s worth it to check it out.

Walk through Sydney Botanic Gardens

It’s about a half hour walk from Darling Harbour, across the city to Wooloomooloo for lunch. We decided to break it up by strolling through the Botanic Gardens.

Sydney Botanic Gardens is spectacular in that, just like everything else on this list, it’s right on the waterfront. We found a beautiful little lake (full of eels, apparently!) that was so peaceful. A shady spot to enjoy the views of the harbour.

Lunch at China Doll (or elsewhere in Wooloomooloo)

So in doing a bit of research prior to this trip (a rare weekend without kids requires mucho planning to get the most out of it) I got the impression that China Doll was THE place to eat. Given it was our anniversary I was happy to spend some money on a nice place for dinner. Unfortunately, we couldn’t get the Saturday night dinner reservation but Sunday afternoon worked well too.

I’ll be honest. It was really lovely: fresh food and anextensive cocktail list – and the wine list is huuuuge! But it wasn’t the mind-blowing experience I expected. Some of that comes from living in a famous food and wine region – we’re so spoilt. One thing though, I don’t usually eat pork. We ordered the banquet and there was quite a lot of pork in it, so I’ll give China Doll this – they got me to enjoy pork!

China Doll is on the famous Finger Wharf in Wooloomooloo. I don’t think we ate in a single establishment that wasn’t on the water the whole weekend, and Finger Wharf is just another iconic waterfront spot. China Doll is just one of many amazing-looking restaurants here, so make sure you head here for lunch and enjoy the sunshine.

Laze about in Hyde Park

It’s a little bit of a walk back to the hotel from Finger Wharf… though nothing we weren’t used to after covering such distances by foot all weekend.

We chose to walk back via Hyde Park, and just sit for a while and take it all in. A last-ditch effort to enjoy some serenity before going home to kids, maybe? 

I loved looking over at St Mary’s Cathedral while sitting in the shade and watching everyone walk by. A perfect spot to digest lunch! 

There are many places you could while away an afternoon in Sydney while waiting for your flight. If shopping is your thing, why not hit up Pitt Street?  But a laze in the park was perfect for us. After sitting in the park for a while, we went and picked up our luggage up and caught the train back to the airport. 

So there you go – our weekend itinerary in Sydney with no kids. A little bit of romance, a little bit of relaxing, a whole bunch of walking and waaaaay too much eating. 

Below are some tour ideas I love, too.

Next time we’re in Sydney we’ll probably be with the kids. Which is great – New South Wales is a fantastic destination to explore with kids. If you’ve been following this itinerary and you’re keen to explore more of New South Wales, my friend Emma over at Small Footprints Big Adventures has written a great post about Mungo, so go check that out!

Love a good Australian weekender? Looking for something other than Sydney? Why not try Melbourne or South Australia’s McLaren Vale?

Love this post? Do me a favour and share it!

Cover image by Chris Fuller (Unsplash)