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Sydney in 5 Days

Flying from Toronto to Sydney, Australia alone for only five days is crazy right…is it?  This is my five day journey to Sydney through the sleepy, hazy eyes of wicked jet lag.

FYI: I had a $400 credit from United Airlines and I found an $880 flight from YYZ to SYD with a layover in LAX, thus the flight only cost me $440. I had gold status with United Airlines (Star Alliance) which enabled me to upgrade to Premium Economy; extra legroom at the front of the plane for no additional cost.  More importantly Gold Status on Star Alliance gives you access to Business Lounges during your entire journey roundtrip.

Day 1: Arrive at 6:30 AM after time traveling across the globe. First things first I need to take the train to Sydney then a bus to Bondi Beach. You will need to purchase an Opal Card in order to use the transit system. You can use the card to pay fares on the train, bus and ferry.  A one-way from the International Airport Terminal in Sydney to the Circular Quay-Harbor Front stop is $17.38 AUD or $12.37 USD.  The subway and bus are very easy to navigate. Considering I was jet lagged and on some serious anti-air-sickness medication when I landed I was still able to find my Hostel without any issues. I put $30 on my Opal card knowing I was going to be going in and out of downtown Sydney from Bondi Beach for the next 3 days and eventually back to the International Terminal at Sydney Airport.

STAY: The first 3 nights I stayed in a private room at the Bondi Backpackers Hostel. You cannot beat the location as it is right across the street from the beach. It appears as though they have renovated since I visited. I’m not sure if they still offer private rooms however, they now offer free rooftop yoga classes along with free breakfast.

My last 2 nights were spent in Sydney Harbour YA Hostel-The Rocks. It’s more expensive than a regular youth hostel, but it shares the view of Sydney Harbour with the Shangri-La Hotel, which goes for $250+ a night.  This Sydney YHA is built above and a archeological colonial site.  The rooftop deck offers stunning sunrise and sunset panoramic views of the Sydney Harbour, Opera House and the Harbour Bridge.

Arriving at Bondi Beach I take a long deep breath. The salt air wakes me up briefly, and I decide to do the famous Bondi to Coogee Coastal Walk. After all it is still Springtime in Australia and that can mean rain, so overcoming jet lag to enjoy a beautiful day was a no brainer.

The Bondi to Coogee Coastal Walk is a unique cliffside walk with spectacular views of the Pacific Ocean. If you are not up for the long walk op instead for the Bondi to Bronte portion.  This portion of the walk is only 3 km round-trip.  You can continue on to Coogee to complete the full coastal walk. Be sure to walk through the cemetery for some spectacular views.  Along the way there are restaurants, restrooms, pools, cliffs, and beaches for a quick dip to cool off. Keep going as long as you can as the views and serenity are priceless.  My body finally succumbed to jet lag around Gordon’s Bay.  I turned around bee-lined it for the hostel and slept straight until 2 AM.

Bondi to Coogee Coastal Walk

Day 2: You must I mean absolutely must get breakfast at Bills| Restaurant. Lucky for me they have a Bondi Beach location right up the street from the hostel.  Don’t over think it.  I ordered the scrambled eggs, sourdough bread, fresh tomato-cumin roast tomatoes and miso mushrooms. I don’t know what they do to the eggs here, but my god these are the beast scrambled eggs I have ever eaten. I think they could just be scrambled in pure cream.  Either way they are spectacular.

I talked to the server at Bills, who turned out to be from a few towns over from where I grew up.  He gave me a list of some really good bars, restaurants and coffee shops to check out while in Sydney.

PRO TIP:  Always ask servers and bartenders at the trendiest places for food, drink and entertainment suggestions. They have their finger on the pulse of the city.

Here are his suggestions:

Since time was of the essence on this trip I chose the recommendations in Surry Hills over the ones in Potts Point. Location and time to and from Bondi were the main reasons for this decision.  Surry Hills is a stylish area of town with trendy cafe’s, bars and restaurants.

Following breakfast I headed straight to Ruben Hills in Surry Hills for an excellent cup of Joe. Ruben Hills is a micro roastery located in a beautifully designed space. Did I mention drinking a cup of coffee in Sydney, Australia isn’t like anywhere else in the world.  Sydney is to Coffee as Bordeaux is to wine and drinking a cup of coffee at Rueben Hills is a well thought out journey of single sourced beans from lands far away to single herd Australian milk.  You are also going to pay an enormous amount of money for this coffee as food and drink are not cheap in this country/continent located down under. A short cup is going to be upwards of $4 AUD.  On the plus side you will never have a coffee experience quite like this again.

After a “get to know you” stroll around Surry Hills I head over to Nomad for lunch.

PRO TIP: A great way to get into a hot and trendy restaurant without a reservation is to go to an early or late lunch or an early dinner-90% of the time I usually get seated right away. I have waited up to 30 minutes to be seated before, but I have never been turned away for a table.

Since I was a solo diner I was seated at the kitchen bar, which ended up being a treat. From my viewpoint I could watch head chef Jacqui Challinor at work with her team.  She quietly and methodically directed her large kitchen staff from the expo station all the while chopping up Brussel sprouts for their famous appetizer and finishing off dishes for diners with a sauce drizzle or sprinkle of spice.  Having first hand view of this performance made my dining experience that much more special.  The food was divine and yes I ordered the Brussel sprouts.

My vantage point of Chef Jacqui Challinor located in the top right of this pic reaching for a order ticket

Before leaving I asked my server for any bar suggestions in the area. You see Sydney is full of hidden speakeasy bars. My goal is to spend my nights seeking out these top notch bars.  I already new about area favorite, The Wild Rover, but she suggested The Button Bar, a bar I did not know about prior to my trip,  which I hit up later in the evening.  It is only 1:45 PM, so I decide to walk down to the new trendy up and coming arts/entertainment area called Chippendale aka the Chippo. Scott Marsh, a local street artist had recently put up the controversial “Kanye Loves Kanye” mural in the area. I decide to go on a scavenger hunt to try and find it.  I find the exact wall where Marsh had painted it, but another mural has replaced it.  You see, Marsh had agreed to paint over the mural if he was paid a $100,000 ransom. Marsh claims Kanye West paid him the fee. Kanye claims he didn’t. Either way the mural has been replaced with another piece.

Located down Teggs Lane diagonally across from The Chippo Hotel; “Kanye Loves Kanye” on the left and the replacement mural on the right
Biggie Smalls by Scott Marsh on Chippen Lane

The area is host to cool eateries and bars as well as a great Chinese contemporary art gallery named The White Rabbit, which was closed for a changeover in artwork (they have two pieces by Ai Weiwe).  It is raining, a lot, so I hit up The Chippo for refuge and a beer after the 50 minute walk from Surry Hill. They have fantastic burgers and a cool vibe.

I start my walk back to Surry Hill for Happy Hour at The Wild Rover.  It is raining so hard I cave and buy an umbrella. Not just any umbrella, but a long walking stick style umbrella. (I brought it all the way back to Toronto with me on the flight home).

The Wild Rover is not easy to find, but it’s worth the search. Use the pics below as helpful clues while walking down the street.  I walked in a little after 4PM knowing the bar gets packed quickly.  Sure enough right before 5PM the bar was packed and there was a line to get in.  Since I arrived early I asked the bartender to make me something interesting with whiskey.  He provided me with this fire fueled potent whiskey concoction. It was fantastic. The atmosphere, drinks and food at this cleverly clad bar are fantastic.  The drinks range from $17 to $21.  This is standard cocktail fair in Sydney. The price is high, but the drink is usually strong and delicious.

The Wild Rover
The Front Door
Custom Wallpaper

Fire Drink at The Wild Rover from One Bag Wanderlust on Vimeo.

Bottoms Up!

After The Wild Rover I walked my way over to The Button Bar, which is a pretty small pirate themed bar.  I was there by 7 PM and there wasn’t a seat to be had. The drink I chose is no longer on the menu, but so delicious.

The Button Bar
Button Bar Cocktail

Day 3: I started the day at the Museum of Contemporary Art Australia. Admission is free and the harbour views from the MCA Sculpture terrace are stunning (located outside of the MCA cafe).

I really wanted to see the inside of the Sydney Opera House, but admission is $40 per person to tour the building when it’s dark.  So, instead I got lucky and found an event taking place in the main hall; Festival of Dangerous Ideas was going on and I booked a ticket to see Break A Rule A Day by Lionel Shriver (Author-We Need to Talk About Kevin).  Not only did I get to see inside of the Sydney Opera house I was able to see and enjoy the acoustics during a live performance.

Festival of Dangerous Ideas

PRO TIP: Search local papers and online for Things To Do Today or This Week while you are in a city. There are a number of listings ranging from free things, to arts, food, concerts and sports . It’s a great way to discover fun things to do while traveling.

Following the event at the Opera House I headed up to the Art Gallery of New South Wales. Since I had checked Things To Do Today and This Week I discovered the gallery was hosting a video installation entitled MANIFESTO by renowned German artist Julian Rosefeldt starring famed Australian actor Cate Blanchett.  Since Cate Blanchett is an Australian national treasure I gladly paid the additional exhibition admission fee to see it. You can watch the entire film installation broken down into it’s original display segments here. The film is worth the time and is a perfect example of why Kate Blanchett is a two-time Oscar winner.

After the museum I headed downtown to Frankie’s Pizza a very famous local late night establishment with great pizza, pinball and live music to refuel after a day of walking and to prepare for some night drinking at a few downtown speakeasy’s.

Frankies has a hidden bar of its own.  There’s a backbar-within-a-bar tucked away inside 50 Hunter Street. The Backbar was originally set up as a space for bands to hang out after their sets. Now it is open to those who know how to find it. Ask the bartender when it opens since it tends to open later at night.

When you’re in the main concert room, head past the bar to the fire door to the right of the stage (see the high white light to the right of the stage pic above) open it up and head downstairs. Don’t worry you won’t set an alarm off. Open the door at the bottom, where you’ll find a tiny bar with three booths, beer on ice and a nearly private bar to chill in.

Now it’s off to The Baxter Inn a standard on The World’s Best 50 Bars list for the past few years.  It’s one of the most difficult bars to find on my list of Sydney speakeasy’s. I tried to find it based on the clues I read online, but found myself back out on Clarence Street staring at my written instructions stumped. At that moment, a whooping of laughs and jeers comes around the corner. A man is dressed as a cheerleader wearing terrible makeup followed by a gaggle of happy guys; a bachelor party… that I am certain is heading to The Baxter Inn.  I decided to confirm my hunch with the last straggler in the bunch. “Are you heading down to The Baxter Inn?”  The jovial party participant replies  “Yes, follow us!”.  So I do and realize where I made my mistake trying to find the entrance. I didn’t turn and walk all the way to the right. There was now a bouncer standing outside of the tricky door.

Apparently, the bar now puts a red rope que outside the door every night for the lineup waiting to get in.

I arrive at opening in order to ensure a spot at the bar. The Baxter in is “Whiskey Heaven”.  The bartenders climb the bar like an in-house library pulling down whiskey’s from around the globe, which are posted on a board that looks like it use to be hanging on an old stock exchange wall.  The bartenders are knowledgeable and helpful when it comes to choosing a whiskey from the very heavy and thick leather-bound menu.

After a drink it was on to The Lobo Plantation and Papa Gedes Bar. Two more underground speakeasy bars that wow with unusual decor, fantastic drinks and all around good vibes.

The Lobo is the easiest to find thanks to the giant sign above the door.  When you step down through the winding staircase it serves as a time machine harking back to a southern charm-style bar with fine leather seating and even finer drinks.  The ambiance beckons you to stay for a while.

The Lobo Plantation staircase

Next and the final stop of the night before catching the bus back to Bondi Beach is Papa Gedes Bar. This bar is one of my favorites.  It’s hidden well, designed well from decor, to glassware to a very stylized menu.

Alley leading to Papa Gede’s
My drink-Smokey South Julep

Day 4: Time to head into Sydney for good. I wake up early for breakfast and for one last stroll around Bondi Beach before I pack up my bags to take my last bus ride to the Harbourfront .  Next stop:  Sydney Harbour YA Hostel-The Rocks. I was able to secure a bed in an all-woman’s dorm room (6 bunks). Only 3 of the 4 beds were occupied, which made for nice sleeping.

Sydney Harbour YA Hostel-The Rocks
Sydney Harbour YA Hostel-The Rocks-Rooftop View

Today will be spent on a free walking tour.  I’m Free Walking Tours provides 2 daily Sydney Sights Tours (Every Day at 10:30 am and 2:30 pm) and 1 Nightly Rocks Tour (at 6PM).

The Sydney Sights tour is a 2 1/2-3 hour tour starting at Town Hall Square (George St. between Sydney Town Hall and St Andrew’s Cathedral).

Rocks At 6PM Tour is a 1 1/2 hors tour starting at Cadmans Cottage (water side) The Rocks District/Circular Quay.

I ended up taking both tours in one day.  The amount of history you will receive on these tours is fascinating. You will get deep background into the Sydney Opera House and the tour brings you to the perfect sunset picture spot.

PRO TIP:  Free Walking Tours are offered in most major cities. I highly recommend taking one as they will help you get acquainted with the city quickly while teaching you interesting historical facts that you might otherwise never learn.  You can pay what you like, but be fair. I normally give the equivalent of $15-$20 USD when I take a tour.

Sydney Town Hall
Queen Victoria Building-Sydney
Hyde Park Fountain-Sydney
St Mary’s Cathedral-Sydney
St. James Church-Sydney
The “Rum” Hospital-Sydney
Red Dress Scene from The Matrix-Martin Place-Sydney
Red Dress Scene from The Matrix-Martin Place-Sydney
Angel Place Bird Cages-Sydney
Sydney Tower Eye
Cadmans Cottage-The Rocks
The Harbour Bridge-Sydney
The Sydney Opera House-Sydney

It’s nighttime again and you know what that means…off to another of Sydney’s hidden bars.

Tonight I am hitting Grandma’s Bar. A retro-sexual rum den decorated in what can only be described as grandma style.  The drinks here are interesting and rum soaked.  If The Baxter Inn is “Whiskey Heaven” than Grandma’s is “Rum Purgatory”; one must purify the soul with glorious barrel aged rum before moving on to the next life.

I instantly hit it off with the fine bartenders at Grandma’s. So much so they bust out the good stuff for me to sip on. Needless to say Grandma’s was my last stop of the night.  I ordered the Peanut Butter Colada and a Chicken Jaffle for counter balance. Jaffles are Australians version of bar food. They are long toasted bread concoctions with different toppings and cheese. Mine had chicken, cheese, onions and jalapeño mayo.  The rest of the night was spent talking with the bartenders and sampling various drinks they were making for other customers. It was a good thing I moved down to the Rocks this morning as the Bondi bus trip back may have been a wee bit treacherous.

Grandma’s Bar-Outside
Grandma’s Bar Door
Grandma’s Bar Staircase
Grandma’s Bar-Inside
Peanut Butter Colada

Day 5: For one of the best views of the Sydney Harbour simply take a ferry ride.  I took a 12 minute ferry ride over to Sydney’s Taronga Zoo from the Circular Quay terminal. The round trip ticket is $7.32 AUD or $5.20 USD.  You can pre-pay for your Zoo ticket online and save 20% off or you can pre-purchase your Zoo tickets at the Wharf 4 ticket booth before you board. Having your ticket in advance will enable you enter the Zoo via the Sky Safari located just to the left of the Ferry Terminal exit.  I did not pre-pay for my ticket which resulted in waiting for a bus to bring me up the mountain to the Zoo entrance.

Zoo Entrance Outside of Ferry Terminal

Sydney’s Taronga Zoo One day entry rates:

Adult $47.00 $42.30
Concession $37.00 $33.30
Child (4-15 years) $27.00 $24.30
Infant (under 4 years) FREE FREE

Sydney’s Taronga Zoo Hours:  9.30am – 5.00pm. Taronga is open every day of the year, including Christmas Day.

PRO TIP: When the Zoo opens go directly to the Koala Habitat and wait for activity.  According  to the Zookeeper the Koalas sleep about 18 hours a day due to all the Eucalyptus leaf consumption. As you can see they were up and about eating for only 30 minutes and then went right back to sleep for the rest of the day.  I kept checking throughout my time at the Zoo for activity. Each time I popped in for a visit they were all cuddled up and snoozing.

Active Koalas
Sleeping Koala


Hands down Taronga Zoo is the coolest Zoo I have ever visited. First of all the Emu, Wallaby and Kangaroo area was a walk through zone. This means exactly what you think it means. You are in the pen with an animal known for punching humans and the worlds biggest bird with only one way out.

Tasmanian Devil

I spent considerable time at the Zoo reading, exploring and catching the spectacular views of downtown Sydney.

After 4 or 5 hours at the Zoo I took the ferry back to the Quay where I spent the remainder of the day walking around the Harbour Front and through the Botanical Gardens.  The Botanical Gardens are free and a great place to hang out on a warm spring or summer day.  Be sure to check out the Wollemi Pine-thought to be extinct for millions of years it was discovered by a hiker in 1995 only 150 km NW of Sydney in Wollemi Valley.

Views from the Botanical Garden
Art installation at the Botanical Garden

Following the day long walk-about I head to my final bar of the trip – Stitch Bar. You need a few clues to find this bar as from the street it looks to be an old run down alterations shop.  It is not.  The clue are the signs that read capacity 80 along with the no-one under 18 sign.  Stitch Bar is yet another speakeasy that worships the whiskey.  I choose the “High & Tight” for the name as well as the ingredients.

Tonight is my last night in Sydney and I am exhausted, however I have unfinished business at Grandmas’ Bar, so I quickly calculate the whiskey to coffee ratio in my drink hoping the caffeine will overtake my sleepiness.  It does and I stay out until midnight talking with the barkeeps and patrons of Grandmas’.

Walk through these beat up doors to reach the stairway that leads down to the bar

Day 6: Time to leave Australias’ most populous city and head back to Toronto.  I ride the train back to the airport earlier than necessary to check out the two business class lounges. Air New Zealand and Singapore Airlines both have business class lounges in my departure terminal.

Air New Zealand had the most amazing breakfast I have ever seen, while Singapore Airlines had a very zen like feel to it.

PRO TIP:  If you are new to an airport ask the check-in agent for a terminal lounge recommendation. My check-in agent told me hands down Air New Zealand has the best food. She was 100% correct.

The End of A Journey:

I understand that five days is not long enough for most people to take the 15 hour flight to Australia. Once I arrived in Sydney I realized the countries greatest export – it’s people.  During my five day visit I was told I needed to see Melbourne, the Blue Mountains, to drive up the Gold Coast or to head cross-country to the desert and onto Ayers Rock. I realize my trip was incredibly short, but I also know the I am not finished exploring this vast and beautiful country.  On this trip I was simply compelled to dip my toes in it’s sparkling sapphire waters.


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