Sydney offers a mix of beaches, concrete and nightlife. Many of my friends and acquaintances have been visiting Sydney since borders opened so I decided to check out this Australian city for myself. Here’s our Sydney itinerary with what we did while we were in the capital city of the state of New South Wales.

Note: this Sydney Itinerary starts on a Wednesday (day 1) and is arranged in a way that you’re able to check out spots that only open on certain days (more on that as you read on).

Overview of this Sydney Itinerary

Day 1: Bondi, Diamond Bay Reserve, Watsons Bay

Bondi

Start off your Sydney adventure in Bondi, home to the most famous beach in Australia. Besides lounging on the beach, you can also try out a number of walking trails too. One of the most common walks people do is the Bondi to Bronte Coastal Walk, which is around 2.5km. We actually had this planned in our itinerary but were too tired and decided to take it slower instead.

We took a short walk along Bondi Beach and checked out the Bondi Icebergs Club. Since the reviews on the service and food weren’t good, we gave this club a miss, but I’ll still recommend walking over to get glimpse (or photo) of the club.

Diamond Bay Reserve

A short bus ride (or a long walk) from Bondi Beach, the Diamond Bay Reserve area is an area of luxury residences and is known for its dramatic cliff top views of the ocean. We took a bus from Bondi Beach and walked over to the cliff side. If you are up for it, you can also take an hour long walk from Bondi Beach as well. Do be mindful as there are many people living in the area and not to disturb the residents.

Getting there (from Bondi Beach): Take bus 380 from Bondi Beach to Old South Head Rd at Billong Ave, followed by a 400m walk along Diamond Bay Road

Watsons Bay

Watsons Bay was once a fishing village and has now become a waterside venue with magnificent harbour views. Besides eateries and a beach club, there are also a number of treks you can do at Watsons Bay. If time allows, check out the South Head Heritage Trail which leads you to the Hornby Lighthouse, which is located on the tip of South Head.

If you choose to walk from Bondi to Diamond Bay Reserve and then to Watsons Bay, you will also walk by the Macquarie Lighthouse, the longest serving lighthouse in Australia. Do note that the walk will take at least 1 hour 20 minutes and there are some up and downhills, so do take that into consideration when planning your itinerary.

If trekking is not your thing, you can take a ferry into the CBD area from the Watsons Bay wharf.

Getting there (from Diamond Bay Reserve): Take bus 380 from Old South Head Rd at Billong Ave to Old South Head Rd at Salisbury St (this is the final stop of the bus service, so it’s unlikely you will miss it)

Note: If you plan to do walks or check out trails, I’d recommend doing Bondi in a day, Diamond Bay Reserve and Watsons Bay on another day as it can get quite rushed, especially if you want to stop for breaks and photos!

Day 2: Sydney Seaplanes, Sydney Opera House, Sydney Harbour Bridge

Sydney Seaplanes

Take your sightseeing experience to new heights (haha) at Sydney Seaplanes, the largest seaplane operator in Australia. We chose the Sydney Highlights flight, which is a 15-minute flight over Sydney attractions such as Bondi Beach and the Sydney Opera house. We paid AUD 230 per pax, but at the time of writing this, it seems that the price has increased to AUD 260 (≈SGD 244.80). During the flight, the pilot pointed out the various attractions and islands to make sure we knew what we were looking at.

This seaplane experience was the highlight of the trip for me and if you do have the budget to spare, I’d really recommend going for this experience. I booked via their website and a staff member, Hanna, got in touch with me via email to confirm the booking. Do take this into account and not book last minute as the booking confirmation is not immediate. They do not fly on Mondays to Wednesdays. You can ask the staff whatever questions you have via email, Hanna was really patient with my questions and also responded really quickly.

Address: Lyne Park, Rose Bay, NSW 2029 Australia
Website

Circular Quay and the Sydney Opera House

After seeing some of Sydney’s sights from up above, it’s time to take a look at them up close. We took a public ferry from Rose Bay, where Sydney Seaplanes was, to Circular Quay. Circular Quay is a harbour with the main ferry terminal of Sydney. Many ferry services, both the public and private services, pass through Circular Quay.

At Circular Quay, you will also find the iconic Sydney Opera House and Sydney Opera bridge. We took a walk around the area but if you want a nice photo at the Opera House, I’ll suggest coming earlier as the area was crowded.

Public ferry fare from Rose Bay to Circular Quay: AUD 6.43 (≈SGD 6.06)

The Rocks and The Sydney Harbour Bridge

Adjacent to Circular Bay is The Rocks — a neighbourhood rich in history and also where you can get up close with the Sydney Harbour Bridge. A popular activity seems to be climbing up the Sydney Harbour Bridge and we saw many people on it while we were there. We did not try it as it was really expensive and was really out of our budget. Price seem to start around AUD 320 (≈SGD 301) for a 2.5 hour experience.

Aslan Coffee Roasters – The Rocks

We chanced upon Aslan Coffee Roasters while looking for a spot to eat. We got a Toasty with Ham & Cheese to share and a cup of latte each. The total came up to AUD 17.50 (≈SGD 16.50). The toasty tasted alright, I’d give it a 3.5/5, but I’m not a fan of bread so do take that into account. I’d say this cafe is great to get some quiet in as it’s located in a quiet spot of The Rocks, though the cafe itself may be crowded. The service at Aslan was also warm, staff were friendly and more than happy to answer your questions.

Opening hours: Mon to Fri 7am – 3pm, Sat to Sun 8am – 3pm
Address: 25 Nurses Walk, The Rocks NSW 2000

Museum of Contemporary Art Australia

If you’re a fan of museums, you can consider checking out the Museum of Contemporary Art Australia. My friend enjoyed her visit and viewing really interesting art, while I was back in the hotel working.

Opening hours: Tues – Thurs and Sat – Sun 10am – 5pm, Fri 10am – 9pm, Closed on Mondays
Entrance fee: Free
Address: Tallawoladah, Gadigal Country, 140 George Street, The Rocks, Sydney NSW 2000
Website

Maybe Sammy

Winner of the Best Bar in Australasia Award 2021 and 22nd in the World’s Top 50 Bars, Maybe Sammy is a real treat for cocktail fans. We visited on Saturday night at 8pm and queued for around 20 minutes. As Maybe Sammy is a walk-in only venue, the queue during peak periods can get pretty long based on what I’ve read online.

When we visited, Maybe Sammy was running a female-inspired menu — Stardust, with drinks inspired by well-known women throughout history, such as Audrey Hepburn and Marilyn Monroe. As a lover of sweet drinks, I got ‘My Fair Lady’ (AUD 26, ≈SGD 24.50) , as recommended by the waitress and my friend got ‘Natural Woman’ (AUD 23, ≈SGD 21.67) a cocktail with a strong hint of truffle. We both loved our drinks and my drink even came with a little bubble “performance”. Bartenders also started dancing to Rihanna’s ‘Umbrella’, with, Umbrellas, when the song played in the bar. Maybe Sammy definitely lives up to its titles in my opinion.

Opening hours: Wed – Thurs 4.30pm – 12am, Fri – Sat 4.30pm – 1am
Address: 115 Harrington St, The Rocks NSW 2000, Australia
Website | Facebook | Instagram

Day 3: Sydney Fish Market – Surry Hills – Chinatown Night Market

Sydney Fish Market

Sydney Fish Market is an iconic spot definitely a must-visit for all seafood lovers. The highlight of the market is definitely the seafood section. There are a number of stalls in the seafood section, with many of them selling sashimi, sushi and you can even pick out some seafood to have them cook for you. After walking around for a bit, we decided to have our meal at Peter’s.

We ordered 3 sushi (AUD 2.50 each, ≈SGD 2.40 each), sashimi box (AUD 22.50, ≈SGD 21.30), lobster roll (AUD 11, ≈SGD 10.40) and half dozen oyster (AUD $12, ≈SGD 11.36). Oh and if you want Tobasco sauce with the oysters, it’s AUD 2 (≈SGD 1.90) for a tiny bottle.

Though everything we had was fresh, I’d say don’t get the sushi because they are way overpriced. The lobster roll was too salty for my liking, possibly due to the mountain of cheese on it. I’d say the oysters were well worth the price, considering that many spots in Singapore sell 1 oyster for $2.

Opening hours: 7am – 4pm (individual stores may have varying hours)
Getting there (from CBD): Take Lightrail L1 to fish market station

Surry Hills

The suburb of Surry Hills is a creative hub filled with cafes and clothing stores. If you’re into streetwear, you can check out Above the Clouds, P.A.M Store Sydney and Supply Store, to name a few. Thrift lovers can pop into Uturn Recycled Fashion and C’s Flashback.

Getting there (from Sydney Fish Market): Take Lightrail L1 to Central Grand Concourse. Walk towards Elizabeth Street and you’ll be in the Surry Hills area.

Single O

We stopped by Single O for a coffee because we saw great reviews online. Though we are not coffee connoisseurs, we enjoyed the coffees and found the price (AUD 5/cup, ≈SGD 4.73) to be really reasonable for Sydney’s standards.

Opening hours: Mon – Fri 7am -3pm, Sat – Sun 8am – 3pm
Website | Instagram | Facebook

Gelato Messina

Gelato Messina is a pretty famous gelato chain with a number of outlets all over Australia and there happens to be one in Surry Hills. Do try the pistachio praline flavour as it’s really one of the best pistachio-flavoured dessert I’ve had in my life. We actually tried Messina at their Darling Square outlet but I decided to include this in the Surry Hills section as having a gelato break whilst shopping sounds great.

Opening hours: Sun – Thurs 12pm – 10pm, Fri – Sat 12pm – 10.30pm
Address: 389 Crown Street, Surry Hills 2010
Website | Instagram | Facebook

Chinatown Night Market

The Chinatown Night Market is a small Asian night market that opens only on Friday nights was one of my favourite activity of the trip. This little night market is modelled to feel like the Taiwan night markets and quite frankly, although it is nowhere near what a Taiwanese night market is like, I’d say it’s a good experience for foreigners who miss home or those who want a taste of a Taiwanese night market.

Personally, I feel that the food at this night market is pretty expensive but it was already expected as Asian food tend to be expensive in the Western World. I got 2 sticks of squid for AUD 9.50 (≈SGD 8.94), it was really pricey but one of the best food items I had during the trip! Highly recommended. We also got xiao long bao and pan fried dumplings to share (AUD 11 for a box of 4 dumplings, ≈SGD 10.35), but they were only average.

Opening hours: Fridays 4pm – 11pm
Address: Dixon St, Haymarket NSW 2000, Australia

Sydney Seaplanes – Circular Quay and Sydney Opera House – The Rocks and Sydney Harbour Bridge – Maybe Sammy

Day 4: Blue Mountains National Park

Day Trip to Blue Mountains National Park

We got up early to go on a day trip to Blue Mountains National Park. We booked a day tour with Coast Warriors and met up with our guide, Trent, in the morning who took us into the Blue Mountains National Park. Unfortunately, the day was super foggy and rainy, so it spoiled the fun and views.

Glenbrook was our first stop during the trip. The town is about 1 hour from Sydney CBD and a good pitstop for a coffee and toilet break. Next, we did a 90-minute hike to see Wentworth Falls. Though rated moderate, I found the hike to be really tough. What made it worse was that since it was so foggy, we saw nothing throughout the hike. We also tried visiting Lincoln’s Rock and the Three Sisters lookout, but saw nothing. It did clear up for a short while at Three Sisters and by a short while I mean a minute.

Do take the weather into consideration if you’re planning to head to Blue Mountains National Park, especially during the wet seasons as the trip could be all for naught, like ours did.

Tip: Bring a rain jacket, or a warm jacket because it can get cold in the mountains. I didn’t and ended up buying one in Glenbrook.

Price: SGD 103/pax

Koi Dessert Bar

We were dropped off at Central earlier than planned because the horrible weather did not look like it was easing. Since we were in the area, my friend and I decided to try out Koi Dessert Bar, which is owned by 3 brothers, with the youngest of them being a Masterchef star. We ordered a Tiramisu and “Like a Boss”, a cube-shaped cake that has plum, mango and green tea as its main flavours. Each cost AUD 18 ( ≈SGD 16.98) and though the cakes were good with the right level of sweetness, I do not think they are worth the price tag.

Opening hours: 11am – 10pm daily, closed on Mondays and Thursdays
Address: 6 Central Park Ave, Chippendale NSW 2008
Website | Facebook | Instagram

Lukumades

Just a few steps away from Koi Dessert Bar is Lukumades, which sells Greek doughnuts with a large variety of toppings. Unlike the usual doughnut that has a ring in the middle, Lukumades serves small doughnut balls with fillings and topping. We got a box of 10 balls containing 5 Plain Jane and 5 Dark Delight. A tray is AUD 12.90 and you can top up AUD 2 for “half and half”, which allows you 2 flavours in 1 box. I really enjoyed the Plain Jane flavour, which is coated with cinnamon sugar, reminding me of a fluffier version of a churro. The Dark Delight was a little heavy on the flavour and I definitely would not be able to eat more than 2 in a single sitting.

Opening hours: 12pm – 11pm
Address: Shop/2 Central Park Ave, Chippendale NSW 2008, Australia
Website | Facebook | Instagram

Day 5: Manly, Newtown, The Grounds of Alexandria

Manly

Bondi Beach may be Australia’s most famous beach, but did you know that the world’s first surfing competition was held at Manly Beach? Manly is also where you’ll find many shops selling fish and chips. We really enjoyed exploring Manly, much more so than Bondi, because there were more shops and food options here. The Corso (path from the wharf to Manly Beach) has many shops selling surf-wear, souvenirs and food. We spent a long time in the clothing stores and I felt that shopping here was much better than in the CBD because I loved the brands I found here.

Getting to Manly: Take public ferry F1 from Circular Quay to Manly Wharf (30-minute ride)

Manly Fish Market

We were on a hunt for affordable fish and chips and walked past Manly Fish Market, which sells fresh seafood, but also offered a cooked menu. We paid AUD 15.90 ( ≈SGD 15) for a portion of Fish and Chips to share. If you’re not extremely hungry, I would say the portion is enough for 2. The fish was flakey, but skin was not as crispy and fried as my friend would like it to be. On the other hand, I found it to be just nice.

Opening hours: 10am – 8pm
Address: 1/25 S Steyne, Manly NSW 2095, Australia

Bluewater Cafe

We were looking for a spot to have coffee and saw that Bluewater Cafe was packed so we decided to head in. Besides coffees (AUD 4 each, ≈SGD 3.77), we also decided to order a potato rosti (AUD 24.90, ≈SGD 23.50) to share. The rosti was crispy and we chose salmon for our side. The food at this cafe was a tad pricey but it is to be expected as you’re facing the beach.

Opening hours: 6.30am – 8.30pm
Address: 28 S Steyne, Manly NSW 2095, Australia

Manly Markets

The Manly Markets comprises of a fresh produce market, which is only open on Sundays and a craft market, which is open on Saturdays and Sundays. We were very disappointed when we got there, because there were only about 10 stalls, and I felt so deceived by the photos I’ve seen online. The stalls were not interesting either and I definitely would not make a trip to Manly just for the market.

Coastal Walks

Besides chilling on the sand, there are also coastal walks if you can do if you’re a fan of trekking. The 3 most popular ones are Spit to Manly Walk (10km), Walk North Head Sanctuary Walk (8km) and The Manly Coastal Walk (50km). As the walks were all pretty long, we did not have time to try out any of them as we wanted to check out another part of Sydney.

Newtown

Newtown is an area filled with indie shops and thrift stores. Fans of vintage and thrift shopping will be thrilled here. We spent half a day shopping in the area and some of our favourite shops included Storeroom Vintage, Tree of Life and Artisan’s Nest.

Fans of street art can also go street art hunting in Newtown. There are guided walking tours or you also try a self walking tour with all the resources online.

Getting there: Take the train to Newtown station

The Grounds of Alexandria

If time permits, pay a visit to The Grounds of Alexandria, which around 15 minutes of traveling time away. The Grounds of Alexandria is known for its cafes with whimsical decorations and the Lululemon outlet. I suggest only checking this place out only if you have a lot of time to spare and nothing else to do.

Honestly, the Lululemon outlet had nothing in my size (size 4), I even looked at sizes 2 and 6, but nothing good. If you’re coming here just for the Lululemon, with specific clothing models in mind, I would say, don’t bother visiting. The shop was small with few selection. My friend that visited the outlet a month prior also felt the same.

In addition, only 1 bus, with a long waiting interval to boot, serves the bus stop outside The Grounds of Alexandria, making it extremely painful to get to this location unless you are driving.

Dinner at Betty’s Burgers

An Australian answer to Shake Shack, Betty’s Burgers has outlets across Australia. We got the Betty’s Classic, which is an Angus beef burger (AUD 11.50, ≈SGD 10.74), a chocolate shake and vanilla shake for AUD 8 (≈SGD 7.47) each. The beef was juicy and the special sauce was also tasty, I think it’s definitely worth a try while you’re in Australia. On the other hand, the shakes were just average and they taste like liquid ice cream.

Address: Check website for nearby outlets. Sydney outlets include Market Street, Circular Quay and Darling Harbour.

Other spots you can consider checking out

Darling Harbour

Darling Harbour is a waterfront precinct a short walk from the CBD. If you’re looking for a place for a chill evening walk, consider checking out Darling Harbour.

The most popular attractions at Darling Harbour is the SEA LIFE Sydney Aquarium, WILD LIFE Sydney Zoo, which can be a great location to get away from the rain during the wet seasons. Yes, the zoo is fully sheltered! I was also surprised when I found out that the zoo was fully indoors. I’d say the aquarium and zoo are pretty small and can each be covered in less than an hour, but I really enjoyed the engaging animal talks with the keepers.

The admission fees were a pretty expensive though, but they offered discounts if you purchase tickets for more than 1 attraction. The attractions offered are — SEA LIFE Sydney Aquarium, WILD LIFE Sydney Zoo, Madame Tussads and The Sydney Tower Eye.

Entrance fee: AUD 39.20 for 1 attraction, AUD 65 for 2 attractions, AUD 75 for 3 attractions, AUD 85 for 4 attractions
Opening hours: Generally, they are open from 9.30am – 5pm, but opening hours vary, so check the website before heading down

SEA LIFE Aquarium Website | WILD LIFE Sydney Zoo Website | Madame Tussads Website | The Sydney Tower Eye Website

Cantina Ok!

Cantina Ok! is a Mexican-inspired standing bar, that is also one of the Top 50 Bars in the world! Margarita should definitely check this hole-in-the wall bar out but this cozy bar only fits around 20 people so you might have to wait a while to get into the bar.

We got a Margarita Ok! and a Sour Ok! — which a drink topped with whipped coconut, really interesting! They also serve seasonal drinks and you can check out their website for the menu.

Opening hours: 4pm – 2am
Address: Council Pl, Sydney NSW 2000, Australia
Website | Instagram

Getting around Sydney

Public Transport

There are a number of public transport options in Sydney — the train, light rail, bus and ferry are the most common options. Relying on public transport in Sydney is sufficient to get to most places in Sydney and there are even services that take you into Blue Mountains.

To use these services, you would have to get an Opal Card, which is available at convenience stores and transport customer service centres. You can check out the Opal website for more information and find a location to purchase your Opal Card.

From my experience, the intervals between buses can get pretty long and we waited about 20 minutes after missing a bus at The Grounds of Alexandria. Many bus stops in Sydney are marked out by just a pole with an information card stuck to it, so you’ll have to keep an eye out for it.

In terms of navigating around the city, Google maps did a decent job at directing us to the transport service we should use and also provided sufficient information about the next train/bus.

Taxi Services/Private Hire

There are a few taxi services in Sydney — 13cabs and Uber are the most common ones. Prices can get steep during peak hours, but otherwise I think it is affordable, about the same price you would pay in Singapore. We paid AUD 25 (≈SGD 23.30) for a 15 minute ride.