Beyond the Yellow Brick Road

As the Emerald City, Sydney is the gateway to OZ.  It is a cosmopolitan city like no other, yet seemingly familiar at the same time. With stretches of heritage protected Art Deco buildings, common during America’s Happy Days, Sydney feels like L.A.’s love child from the 60s. Sydney is a big city with a small town vibe.  Its sunny skies seems to serve as some sort of invisible force field against anger, evident by its friendly, warm-natured locals.  With 70 beaches nearby, paradise is never far away.  Sydney’s white sandy beaches, clear blue skies and azul waters, beckon the most jaded of travelers.  

Tourist destinations are centrally located and public transportation will easily zip you around to most places.  However, if navigating the city on your own seems a bit daunting, start out with a free walking tour, offered daily at 10:30 a.m., 2:30 p.m. and 6:00 p.m.  For those who want to go it alone, Sydney is a safe, easy to navigate city.  With only a handful of “must see” sites, Sydney should be enjoyed at a leisurely pace.  Your natural inclination may be to charge full steam ahead to see Sydney’s iconic skyline.  The star power of Sydney’s biggest celebrities, the Harbour Bride and the Opera House, cannot be denied.  However, resist the urge to power through and enjoy the slow reveal of Sydney’s sites.

Begin your walking tour at the Anzac Memorial, a war memorial located in Hyde Park, dedicated to all Australians who served their country in war.  Wander through Hyde Park, Australia’s oldest park.  Be sure to stop off at St. Mary’s Cathedral, built in a medieval “Gothic Revival” style during the 19th century.  A free hour long tour is available Sundays after mass at 11:30 a.m.

Continue onto the Royal Botanic Gardens, an oasis of calm in the city center, which offers you a sneak peak of Sydney’s famous Harbour Bridge.  Look for fruit bats in the trees as you make your way down to Mrs. Macquarie’s Chair, a bench hand carved from sandstone by convicts in 1810 for Governor Macquarie’s wife, Elizabeth.  Legend has it that this is where Mrs. Macquarie would watch British ships enter Sydney Harbour.  It is no surprise then that this vantage point offers sweeping view of Sydney’s dynamic duo, the Opera House and the Harbour Bridge, just as famous as Batman and Robin in their own right.

As you continue along the waterfront, you will approach the Opera House’s white-winged sails from the rear.  Designed by Danish architect, Jorn Utzon, the Opera House, Sydney’s most recognizable landmark, was nearly $95 million over budget.  If you do not plan to attend a performance here, but still wish to see the inside of the Opera House, consider pre-booking a tour.

From the Opera House, it is a short walk to Circular Quay, the transportation hub of Sydney, where you can purchase your ferry ticket to Manly Beach, a picturesque 30-minute ferry ride away.  There are many ways to enjoy an afternoon in Manly Beach.  If you want to stretch your legs, the Manly to Spit Bridge Walkway offers a 10-kilometer scenic walk that will take you past Aboriginal sites, coastal heath, and sub-tropical rainforests.  Surf and sand also beckon.  Grab a board and learn how to hang ten at the Manly Surf School or join the locals and engage in a little Southern Hemisphere sun worshipping on Manly’s white sandy shores.  There are endless spots to grab lunch, but Hemingway’s offers an ocean view.

 

On the return trip, sit at the front of the boat for a bird’s eye view of the Opera House and the Harbour Bridge.  If you’re still going strong, consider a pre-dinner pub crawl at some of Sydney’s oldest drinking dens with the Lord Nelson Brewery, Fortunes of War, and Hero of Waterloo each laying claim to being Sydney’s oldest surviving pubs.

Have a siesta before venturing out for dinner.  Darling Harbour, a waterfront promenade is chocked full of bars and restaurants, including Momofuku Seiõbo, David Chang’s first Australian outpost in his New York centric restaurant empire.  The tasting only menu comes at a hefty price, but as the culinary equivalent of the reliable little black dress, Momofuku Seiõbo consistently receives rave reviews.  Café Sydney in nearby Circular Quay is a popular seafood restaurant serving potent cocktails and a million dollar view of the Harbour.  For tasty Thai food with a BYO policy, Thai-riffic at The Spot in Randwick offers an easy-on-the-purse-strings dinner.  Stay for a flick at the Ritz Cinema located in an historic theater built in 1937.

You’ve got a big day ahead of you for your second day in Sydney so you’ll need to fuel up with a hearty breakfast.  Although Bill’s in Surry Hills is always a popular brekkie spot with the locals, venture further a field to The Grounds of Alexandria, located in an old-pie factory, for a farm to table breakfast.  After your breakfast of champions, bounce on over to Bondi.  Hopefully, as part of your vacay due diligence, you’ve caught a few episodes of Bondi Rescue, the reality based T.V. show, centered on a day in the life of a Bondi lifeguard.  Step aside Baywatch this is the real deal with Bondi lifeguards saving over 2,500 people per year, most of whom are tourists!  Bondi Rescue fans will have an inside track on how to avoid the infamous rip currents known as Backpackers Express, an area of particularly fierce rip currents.  Have fun, but make sure you swim between the red and yellow flags!

Do as the locals do and take a stroll on the Coogee to Bondi Walk where the sun-kissed, finely chiseled bodies of the genetically blessed are showcased.  In addition to offering stunning cliff top views, this two-hour walk provides an introduction into some of Sydney’s most popular beaches.  On this walk, you’ll visit Tamarama, often referred to as Glamarama as it is usually littered with Sydney’s beautiful people; Bronte, popular with families and surfers; and Coogee, home to many beachfront bistros.  If you don’t want to walk back, take Bus 353 back to Bondi.

When you’re done with the sun, trade in the Bondi babes and six pack abs for a cold beer and a stunning view of the beach below from your coastal perch at the Bondi Icebergs Club  or engage in a little retail therapy at Bondi’s boutiques.  For one-off Aussie handbags, check out local designer Naomi Levi.

You’ve spent the day among Sydney’s glitterati, it’s time to shower off the sand and get glammed up for dinner.  Choose between one of celebrity chef Neil Perry’s restaurants Rockpool, a Manhattan style steakhouse which exudes the kind of confidence that inspires backroom business deals or Spice Temple, serving up haute chinois in a room so darkly lit, you’ll wonder if you’re the only one there who isn’t involved in a clandestine affair.

It’s time to tackle the Harbour Bridge on your third day.  Over it, under it, or on it, how will you handle it?  For those with money to burn and in need of an adrenaline rush, the Bridge Climb will give you the ultimate bragging rights.  $300 and 3 ½ hours later you can live the life of Jason Bourne as you climb the catwalks, ladders and stairs for a breathtaking view and join the ranks of Matt Damon, Sarah Ferguson and Kylie Minogue as those who have “climbed” the bridge.  The Pylon Lookout, 87 meters above sea level, is a more economical option and one that Cookie Monster, Elmo, and Stuart Little chose.  Or opt for the free option and walk across the bridge, only a thirty-minute journey.  When you get to the other side, a huge smiling clown face will be there to greet you at Luna Park, a traditional carnival amusement park that has been opened since 1935.  Indulge your inner child and take a spin on the Ferris wheel.

Take the train back to the Central Business District and spend the afternoon shopping at The Rocks, Sydney’s historical district lined with specialty shops.  For inexpensive aboriginal art, boomerangs, didgeridoos, and the like head to Chinatown.  If you’re in the market for something a bit more unusual then Surry Hills is your shopping destination du jour.  Elements I Love, stocks one-of-a-kind home wares and antiques.  A portion of all proceeds helps fund the Sambhali Trust, an organization committed to educating India’s women and children.  Other favs include Chee Soon & Fitzgerald and Edit.

Surry Hills, a nouveau bohemian inner suburb full of Victorian terraced house, converted warehouses, and quirky boutiques, is one of Sydney’s hottest hoods and the perfect spot to spend an evening.  Surry Hills is the epicenter of Sydney’s café culture, foodie scene, and small bar nightlife.  You can find all types of cuisine ranging from Italian, American, and Spanish to more exotic flare such as Mauritian, Malaysian, and Lebanese.  Pizza e Birra, a popular Italian eatery has locals declaring it the best pizza joint outside of Italy and it packs em in ever night.  For South American flare, Porteno, an Argentine restaurant is the place to be.

Sydney’s nightlife was once limited to mega-clubs and hotel bars with poker machines.  Thankfully, due to a recent liberalization in Sydney’s liquor laws, “small bars,” have been popping up.  These pint-sized watering holes, often tucked away in basements and alleyways with little or no signage, have a speakeasy feel.  There is no shortage of spots for pre-dinner cocktails in this area of town.  Lil Darlin is an intimate bar known for its potent elixirs, well priced wines, and tapas.  At the other end of the spectrum, Shady Pines Saloon, with its oversized taxidermy animals, aims for an upscale wild, wild, west American honky tonk bar, is also a fun option.   As you throw a few back, you’ll realize that Aussies truly know how to live the good life.  Now go mingle!  See if you can find a good Aussie Sheila or bloke with whom you can take up residence as you’re unlikely to ever want to leave and your visa won’t last forever!

 

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