WHAT TO DO
Sydney is the state capital of New South Wales and the most populous city in Australia and Oceania. Located on Australia’s east coast, the metropolis surrounds Port Jackson which contains the waters of picturesque Sydney Harbour. Indigenous Australians have inhabited the area for at least 30000 years, and thousands of engravings remain throughout the region, making it one of the richest in the country in terms of Aboriginal archaeological sites. During his first Pacific voyage in 1770, Lieutenant James Cook and his crew became the first Europeans to chart the eastern coast of Australia, making landfall at Botany Bay and inspiring British interest in the area. In 1788, the First Fleet of convicts, led by Arthur Phillip, founded Sydney as a British penal colony, the first European settlement in Australia. Phillip named the city Sydney in recognition of Thomas Townshend, 1st Viscount Sydney. Over the next century, it transformed from a colonial outpost into a major global cultural and economic center. After World War 2, Sydney experienced mass migration and became one of the most multicultural cities in the world. Today, this wonderful place is the first stop on many Australian itineraries, and for good reason. It’s an inviting blend of the exhilarating and easygoing – where you can enjoy fine museums, impressive architecture, delicious food and excellent beaches.
Start your adventure in Circular Quay and The Rocks. The birthplace of both the city and the nation, this compact area combines the historic with the modern. Nearly every visit to Sydney begins at the magnificent Sydney Opera House. Designed by Danish architect Jorn Utzon and opened in 1973, this UNESCO World Heritage listed building is Australia’s most famous landmark. Visually referencing a yacht’s sails, it’s a soaring, commanding presence. The complex comprises five performance spaces for dance, concerts, opera and theater. The best way to experience the building is to attend a performance, but you can also take a one hour guided tour. Note: ongoing renovation work, scheduled to be completed in 2022, may disrupt visits. Southeast of the Opera House, the Royal Botanic Garden was established in 1816 and features plant life from around the world. Within the gardens are greenhouses with palms and ferns, as well as The Calyx, a striking exhibition space featuring a curving glasshouse gallery with a wall of greenery and temporary plant themed exhibitions. The gardens include the site of the colony’s first vegetable patch, but their history goes back much further than that – long before the convicts arrived, this was an initiation ground for the Gadigal people of the Eora Nation (indigenous Australians). Note: park maps are available at any main entrance. From the park, it’s a short stroll over to the Museum of Contemporary Art. The MCA is a showcase for Australian and international contemporary art, with a rotating permanent collection and temporary exhibitions. Aboriginal art features prominently. The art deco building has had a modern space grafted on to it, the highlight of which is the rooftop cafe with stunning views of Sydney Harbour. Note: the museum is open every day from 10a-5p.
Nearby is the fascinating Rocks Discovery Museum. Divided into four displays – Warrane (pre-1788), Colony (1788-1820), Port (1820-1900) and Transformations (1900 to the present) – this small, excellent museum, tucked away down a Rocks laneway, digs deep into the area’s history on an artifact rich tour. Sensitive attention is given to the Rocks’ original inhabitants, the Gadigal (Cadigal) people, and there are interesting tales of early colonial characters, not to mention some historical pubs (more on this later). Note: the museum is open every day from 10a-5p. After gaining some knowledge about The Rocks neighborhood, wander its cobblestone lanes and check out the open air markets in the shadow of the Sydney Harbour Bridge. Sydneysiders love their giant ‘coathanger’ bridge, which opened in 1932. The best way to experience this majestic structure is on foot. Stairs and lifts climb up the bridge from both shores, leading to a footpath on the eastern side (the western side is a bike path). Getting the train to Milsons Point and walking back towards the city is the most spectacular. Climb the southeastern pylon to the Pylon Lookout or ascend the arc on the popular BridgeClimb. The Harbour Bridge is the largest steel arch bridge in the world. The two halves of chief engineer JJC Bradfield’s mighty arch were built outwards from each shore in what was a huge source of Depression employment. In 1930, after seven years of merciless toil by 1400 workers, the two arches were only feet apart when high winds set them swaying. The coathanger hung tough and the arch was finally bolted together. Extensive load testing preceded the bridge’s opening two years later. Wrap up The Rocks with a visit to the Sydney Observatory, located at 1003 Upper Fort Street (Millers Point). Built in the 1850s, Sydney’s copper domed, Italianate sandstone observatory squats atop Observatory Hill, overlooking the harbor. Inside is a collection of vintage apparatus, including Australia’s oldest working telescope (1874), as well as background on Australian astronomy and transits of Venus. The observatory was originally built to determine the correct time via astronomical observations. On the roof, a signal ball still drops at exactly 1p. The hill was also used to signal to ships from two high flagpoles, one of which has been reconstructed. Note: the observatory is open every day from 10a-5p.
The Art Gallery of New South Wales can be found on Art Gallery Road in The Domain. Opened in 1874, it is the most important public gallery in Sydney and one of the largest in Australia. With its neoclassical Greek frontage and modern rear, this much loved institution plays a prominent role in Sydney society. Blockbuster international touring exhibitions arrive regularly and there’s an outstanding permanent collection of Australian art, including a substantial Indigenous section. While the permanent collection has a strong collection of 19th century European and Australian art, the highlights are the contemporary Indigenous gallery in the basement and the collection of 20th century Australian art, with some standout canvases by the big names of the local painting scene. Look out for Albert Tucker’s scary Apocalyptic Horse, Russell Drysdale’s brilliant gold town street Sofala and half a room full of Sidney Nolans, usually including one or more of his extraordinary Ned Kelly (famous Australian bushranger) paintings. The cafe and restaurant are fine places to hang out, with outdoor seating and views over Woolloomooloo Bay. Construction of a second building is due to be completed in 2021. Occupying space to the north of the existing building, it’s a major project, to be known as Sydney Modern, that will be centered on a new Indigenous gallery and a dedicated space for major touring exhibitions. The construction work shouldn’t affect gallery visits. Note: the gallery is open every day from 10a-5p.
Next, make your way over to Darling Harbour and the Sydney Sea Life Aquarium. As well as regular tanks, this impressive complex has large pools that you can walk through – safely enclosed in Perspex tunnels – as an intimidating array of sharks and rays pass overhead. Other highlights include a two minute boat ride through a king and gentoo penguin enclosure, a dugong, disco lit jellyfish, evolutionary throwbacks and the brilliant finale: the enormous Great Barrier Reef tank, which cycles you through different times of day in the life of coral, turtles, rare sharks and numerous fish. The aquarium’s dugong (similar to a manatee) was rescued after washing up orphaned on a Queensland beach. Attempts to return it to the wild failed, so the Dugong Island enclosure was built. As sad as it is to see such a large marine mammal in captivity, it offers a fascinating and rare opportunity to get close. Needless to say, kids love this place; arrive early to beat the crowds. It’s cheaper to book online, and there are various combo deals with other attractions run by the same company, including the adjacent zoo. Note: the aquarium is open every day from 10a-6p. Complementing its sister and neighbor, Sea Life Aquarium, the Wild Life Sydney Zoo houses an impressive collection of Australian native reptiles, butterflies, spiders, snakes and mammals (including koalas and a walk through kangaroo area). The nocturnal section is particularly good, bringing out the extrovert in the quolls, potoroos, echidnas and possums. The up close look at a sizable saltwater crocodile is also memorable, while upstairs visitors line up for cute koala selfies. Note: the zoo is open every day from 10a-5p. Located at 2 Murray Street in Darling Harbour is the Australian National Maritime Museum. Beneath a soaring roof, the Maritime Museum sails through Australia’s inextricable relationship with the sea. Exhibitions range from Indigenous canoes to surf culture, and from immigration to the navy. The worthwhile ‘big ticket’ includes entry to some of the vessels moored outside, including the atmospheric submarine HMAS Onslow and the destroyer HMAS Vampire. The high production value short film Action Stations sets the mood with a re creation of a mission event from each vessel – excellent free guided tours explain each vessel’s features. Note: the museum is open every day from 10a-5p. Not far away on Bank Street in Pyrmont is the Sydney Fish Market. This piscatorial precinct on Blackwattle Bay moves over 33 million pounds of seafood annually, and has retail outlets, restaurants, sushi and oyster bars, delis and a highly regarded cooking school. Chefs, locals and overfed seagulls haggle over mud crabs, Balmain bugs, lobsters and salmon at the daily fish auction, which kicks off at 6a on weekdays. A new market is being built a little further west, due to open in 2023. Note: the market is open every day from 7a-4p.
Conclude your tour of Sydney by getting out of the city and visiting some outstanding beaches. Definitively Sydney, Bondi is one of the world’s great beaches. It’s the closest ocean beach to the city center (5 miles away), has consistently good waves and is great for a swim. If the sea is angry, try the saltwater pools at either end of the beach. Two surf clubs – Bondi and North Bondi – patrol the beach between sets of red and yellow flags, positioned to avoid the worst rip tides. Thousands of unfortunates have to be rescued from the ocean each year, so don’t become a statistic – swim between the flags. Surfers carve up sandbar breaks at either end of the beach; it’s a good place for learners, too. Note: be sure to stop in at Bondi Icebergs Club, located at the southern end of the beach, for a dip in its famous pool and an adult beverage. Lovely Watsons Bay, east of the city center and north of Bondi, was once a small fishing village, as evidenced by the heritage cottages that fill the suburb’s narrow streets. Note: take the ferry from Circular Quay to Watsons Bay and head straight for Doyles on the Beach Restaurant. Enjoy a dozen Sydney Rock Oysters along with a glass of white wine as you take in the city skyline in the distance. Another lovely ferry ride from Circular Quay takes you north (past the Harbour Bridge and Opera House) to Manly Beach. Sydney’s second most famous beach is a magnificent strand that stretches over one mile, lined by Norfolk Island pines and low rise apartment buildings. About two miles south of Manly, spectacular North Head offers dramatic cliffs, secluded beaches, pretty paths through the native scrub, and sweeping views of the ocean, the harbor and the city. It’s great to explore by bike or on foot, along the Manly Scenic Walkway. Grab a map and plot your own path through the headland, which takes in former military barracks, World War 2 gun emplacements, a quarantine cemetery and a memorial walk commemorating Australia’s military. At the tip, Fairfax Lookouts offer dramatic clifftop views. North Head is believed to have been used as a ceremonial site by the native Cammeraygal people. These days, most of the headland is part of Sydney Harbour National Park.

WHERE TO EAT
Sydney has several great places to eat and enjoy a drink. Start your day at Bourke Street Bakery, located at 633 Bourke Street in Surry Hills. This tiny bakery sells a tempting selection of pastries, cakes, bread and sandwiches, along with legendary sausage rolls – go with the pork and fennel roll. There are a couple of spots to sit inside, but on a fine day you’re better off on the street. Note: there is another location in the city center on Barangaroo Avenue. Not far away at 83 Foveaux Street is Le Monde. Some of Sydney’s best breakfasts are served between the demure dark wooden walls of this small street side cafe. Top notch coffee and a terrific selection of tea will gear you up to face the world, while dishes such as matcha pancakes and truffled poached eggs will satisfy your soul. Also in Surry Hills at 80 Commonwealth Street is Paramount Coffee Project. Polished concrete floors and modern styling make this foyer cafe in the former headquarters of the Paramount film company an appealing space. Light and optimistic, it rotates its coffee so there’s always something interesting brewing. Infinity Bakery can be found at 274 Victoria Street in nearby Darlinghurst. One of Sydney’s standout artisan bakers, it has delicious sourdough and Turkish breads, as well as coffee and a small selection of cafe fare: rolls, pies, croissants and the like. Note: there is another location in Paddington on Oxford Street. My favorite cafe in town is Fine Food Store, located on the corner of Mill and Kendall Lanes in The Rocks. Staff are genuinely welcoming, make very respectable coffee and offer delicious panini, sandwiches and other breakfast and lunch fare. The outside tables on this narrow lane are the spot to be. Note: if you happen to be in town on the weekend, do visit the Carriage Works Farmers Market on Saturday. Be sure to seek out the following vendors: Pepe Saya (butter), Single O (coffee) and Flour & Stone (bakery).
For Lunch, head to Pony at the corner of Argyle Street and Kendall Lane in The Rocks. This stylish spot offers a modern Australian menu featuring the finest cuts of meat, freshest seafood and an array of shared and larger plates. They also have a nice selection of wines and cocktails. I recommend trying the seared kangaroo and beetroot tartare with pepperberry dressing and raspberries. To drink, get the lemon myrtle spritz – proceeds are donated to the New South Wales Rural Fire Service, to aid with the recent bushfires in Australia. Up the road at 225 George Street is The Morrison Bar & Oyster Room. Occupying the heritage listed Johnson’s Building (built in 1912), The Morrison has become a favorite with locals for its contemporary New York inspired interiors, the freshest oysters and spirited atmosphere. Start with a dozen freshly shucked oysters then move on to the duck fat fish and chips with mint and gherkin mayonnaise. Wet your whistle with the Wild Child – a herbal fusion of Tanqueray, eucalyptus and rosemary, blended with the sweetness of raspberries topped with Prosecco. Sake can be found at 12 Argyle Street in The Rocks. Colorful sake barrels and lots of dark wood contribute to the allure of this large, buzzy restaurant. Prop yourself around the open kitchen and snack on delectable popcorn shrimp and maki rolls, or grab a table to tuck into multicourse banquets of contemporary Japanese cuisine.
If you’ve never tried Sri Lankan food, you really should. The place to try it in Sydney is Lankan Filling Station, located at 58 Riley Street in Darlinghurst. A menu of traditional favorites like pol sambol (coconut chili salad), short eats (snacks) and the house speciality, hoppers. These bowl shaped rice flour pancakes are spongy in the middle and crispy on the outside when they’re done right – and they’re done right at this narrow joint. The flavors, spiked with the secret ingredients of Sri Lankan cuisine, like Maldive fish, mustard seeds, freshly grated coconut and curry leaves, are authentic and delicious. Note: this concrete and steel space is always packed, so put your name on the list and grab a drink nearby. If you fancy some afternoon delight, there are a few spots that will gratify your cravings. Close by at 241 Victoria Street in Darlinghurst is Messina. Join the lines of people who look like they never eat ice cream at the counter of the original store of Sydney’s most popular gelato shop – clearly even they can’t resist quirky flavors such as pear and rhubarb, or panna cotta with fig jam and amaretti biscuit. Cow & The Moon is located outside the city center at 181 Enmore Road in Enmore. This cool corner cafe has an array of sinful truffles, tasty tarts and some darn good gelato. For the best chocolate in town, make your way to Haigh’s Chocolates. There are several locations throughout the city, but the one to visit is inside the beautiful Queen Victoria Building on George Street in the Central Business District (CBD).
For dinner, head to Saint Peter at 362 Oxford Street in Paddington. Sydney is synonymous with seafood, but what chef Josh Niland does at his restaurant is take the treasures of the deep to another fathom. Not only does he source with great care and attention, but he also does things to fish that nobody else does: dry aging fillets, using eyeballs as chips, turning offal into things you often end up enjoying more than the flesh. Note: don’t skip dessert – the custard tart is a masterpiece. Just a few doors away at 380 Oxford Street is the excellent Fred’s. Chef Danielle Alvarez’s minimal intervention approach to cooking lets the top quality produce do all the talking at this farm to table hot spot. Watch it unfold in the dreamy open kitchen from the confines of a comfy seat in the rustic dining room or better yet, the chef’s table. I enjoyed the chilled tomato and eggplant soup with pickled eggplant relish and basil, the lamb cutlets with warm tapenade, anchovy butter and tomatoes, and for dessert the fig leaf panna cotta with marsala roasted figs and langue de chat. Note: the restaurant is closed on Monday. Aria can be found at 1 Macquarie Street in Circular Quay. It is a star in Sydney’s fine dining sky – an award winning combination of chef Joel Bickford’s stellar dishes, floor to ceiling windows staring straight at the Opera House, a stylish interior and faultless service. This harborside institution is home to one of the most awarded wine lists in the country. Note: a good value pre and post theater menu is perfect for a special meal before or after a night at the Opera House. Nearby on Level 3 of the Overseas Passenger Terminal is the outstanding Quay. What many consider to be Sydney’s best restaurant matches a peerless bridge view with brilliant food. Chef Peter Gilmore never rests on his accolades, consistently delivering exquisitely crafted, adventurous cuisine. Note: go with the superb ten course menu and be sure to book reservations online well in advance.
Tetsuya’s is located at 529 Kent Street in the city center. Hidden in an art filled villa overlooking a Japanese garden, behind a historic cottage amid the high rises, this extraordinary restaurant is for those seeking a culinary journey to nirvana. Settle in for ten plus courses of French and Japanese influenced food from the genius of legendary Sydney chef Tetsuya Wakuda. Note: the restaurant is closed on Sunday and Monday. Azuma is tucked away on Level 1 of Chifley Plaza on Hunter Street. It is one of Sydney’s finest Japanese restaurants. Sushi and sashimi are of stellar quality and too pretty to eat – almost. Other options include sukiyaki and hot pot DIY dishes and top notch tasting menus. It’s a great place to get acquainted with high class modern Japanese fare. Note: they have a fine selection of sake and Japanese whisky. Finish up at the very popular Mr Wong, found at 3 Bridge Lane. Classy but comfortable in an attractive, low lit space on a CBD laneway, this modern Cantonese eatery has exposed brick colonial warehouse chic and a huge team of staff and hanging ducks in the open kitchen. I highly recommend the roasted Peking style duck and wok fried pippies (surf clams) in XO sauce. Note: reservations are essential.
End your evening in Sydney with a drink or two. Opera Bar can be found on the lower concourse next to the Opera House. Situated on the harbor with the Opera House on one side and the Harbour Bridge on the other, this perfectly positioned terrace manages a very Sydney marriage of the easygoing and the sophisticated. It’s an iconic spot for visitors and locals alike. Not far away at 10 Bulletin Place is the super cool Bulletin Place. A discreet entrance on this little street of cafes and bars conceals the staircase up to one of Sydney’s most talked about cocktail bars. Personable, down to earth staff shake up five great daily creations that are high on zinginess and low on showiness. It’s a small space, so get there early. Note: the bar is through the door to the left of Cabrito and up the ramshackle staircase – it is closed on Sunday. Another rad spot is Frankie’s Pizza, located at 50 Hunter Street in the city center. Descend the stairs and you’ll think you’re in a 1970s pizzeria, complete with plastic grapevines, snapshots covering the walls and tasty pizza slices. But open the nondescript door in the corner and an indie wonderland reveals itself. Bands play here at least four nights a week (join them on Tuesdays for live karaoke) and there’s another bar hidden below.
I think it’s safe to say Aussies like to drink beer. Sydney has plenty of pubs to enjoy a pint or schooner and I would like to share some of my favorites. The Old Fitzroy Hotel is a gem hidden in the backstreets of Woolloomooloo at 129 Dowling Street. This totally unpretentious theater pub is also a decent old fashioned boozer in its own right, with a great variety of beers on tap and a convivial welcome. Sit at the bar, grab a seat at a street side table or head upstairs to the bistro, pool table and couches. Many of the classic Sydney pubs are in and around The Rocks – the oldest part of town. Harts Pub is on the corner of Essex and Gloucester Streets. Pouring an excellent range of Sydney craft beers in a quiet corner near the beginning of The Rocks, this historical building has real character. The dishes are quality pub food, with generous salads, fish and steaks. On weekends, this is enjoyably quieter than other Rocks boozers. The Glenmore Hotel is at 96 Cumberland Street. Downstairs it’s a predictably nice old Rocks pub with great outdoor seating, but head to the rooftop and the views are beyond incredible: Opera House (after the cruise ship departs), harbor and city skyline all present and accounted for. Fortune of War is located at 137 George Street. Operating right here since 1828, this pub was rebuilt in the early 20th century and retains much charm from that era in its characterful bar. It has a solid mix of locals and tourists, and features live music on Thursday, Friday and Saturday nights and weekend afternoons – it’s a good time. Found at 81 Lower Fort Street is the Hero of Waterloo. Enter this rough cut 1843 sandstone pub to meet some locals, chat with the Irish bar staff and grab an earful of the folk and Celtic bands (Friday to Sunday). Downstairs is a dungeon where, in days gone by, drinkers would sleep off a heavy night before being shanghaied to the high seas via a tunnel leading to the harbor. Lastly, there is the Lord Nelson Brewery Hotel at 19 Kent Street. This atmospheric boozer is one of three claiming to be Sydney’s oldest (all using slightly different criteria). The on site brewery cooks up its own natural ales – a pint of dark, stouty Nelson’s Blood is a fine way to partake.

WHERE TO STAY
Sydney offers a number of places to call home during your stay and there are 2 that I especially enjoyed. Both are in prime locations and provide exceptional service, modern amenities and comfort. The first is The Langham, located at 89 Kent Street in The Rocks (Millers Point). This elegant hotel on a quiet street is a brief stroll from the Museum of Contemporary Art and the Sydney Opera House. Featuring harbor or skyline views, the sophisticated rooms offer free WiFi, flat screen TVs, minibars, and tea and coffee makers. Upgraded quarters add living areas and some have private terraces or balconies. Amenities include a refined restaurant, afternoon tea and a high end spa.
A second option is QT Sydney, located at 49 Market Street. Housed in the landmark State and Gowings buildings in the city center, this polished hotel is next to the lovely Queen Victoria Building and not far from the Art Gallery of New South Wales. Stylish rooms with custom furnishings and walk in showers have flat screen TVs and complimentary WiFi, as well as minibars. Upgrades add soaking baths, balconies and separate living rooms. Other perks include a sleek restaurant, a sophisticated lounge and a deluxe spa.
Sydney has wonderful culture, excellent museums and fantastic restaurants. It treated me well and I look forward to returning.