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Sydney, Australia: Insider’s Guide

by | February 16, 2019

The insider advice on this page is from one of Wendy’s Trusted Travel Experts for Australia: Stuart Rigg of Southern Crossings.

Trusted Travel Expert
Stuart Rigg

Stuart, a native Brit based in Sydney, plans tailor-made travel to Australia, covering the length and breadth of the continent. He has personally tested nearly every property, heli-tour, yacht charter, and waterfront restaurant that he recommends. Stuart has the pull to arrange access to private homes, golf courses, and art collections, but his itineraries aren’t just for high flyers. He can work with a range of budgets, offering careful guidance on everything from self-drive itineraries through the Margaret River wine region to sailing trips around the Whitsundays. As for the Great Barrier Reef, Stuart has failsafe strategies for steering clear of the masses, and he knows exactly which island properties are best for hyperactive families, spa-loving hedonists, or Robinson Crusoe fantasists. If you’d like to combine Australia with New Zealand, his Auckland team will take good care of you. He does not arrange airline travel to Australia, so if you’re looking for a complete package including airfare, write to Ask Wendy.

Travel arrangements start at $750 per day for two travelers.

Where to Stay and Eat

Best bang-for-your-buck hotel
Built over the water at the foot of the Sydney Harbour Bridge, the heritage-listed Pier One Sydney Harbour blends history—the pier was originally constructed in the early 20th century to handle cargo and passenger ships—with contemporary style and comforts. Close to theaters, cafés, and the new Barangaroo parklands (see “Prime Picnic Spots”), the hotel’s character-filled guest rooms are well situated and provide excellent value for money. Enjoy stunning harbor views from the Gantry Restaurant and Pier One Bar; the hotel’s private pontoon offers the perfect launch pad to explore Sydney’s harbor by water taxi or private charter yacht. Book a Waterside Room on the second floor, as those have windows that open to let in the fresh air; 217, 218, and 219 have the best views over Walsh Bay.

Restaurants the locals love
Fred’s in Paddington is a great place to join the locals for daily changing menus of deliciously prepared seasonal produce and genuine friendly service. The warm decor and central open kitchen also give this restaurant a relaxed, homey feel. Head downstairs to Charlie Parker’s speakeasy-style bar for botanically inspired pre-dinner cocktails or an equally innovative nightcap.

The Boathouse Shelly Beach, in the beachside suburb of Manly, is the perfect place to enjoy a morning coffee or that classic Australian lunch—a bucket of fresh prawns—while watching Sydneysiders at play. The beachy setting, with indoor and outdoor tables at the end of the sand at Shelley Beach (a ten-minute walk from the more touristed Manly Beach), is popular with locals for breakfast, lunch, and everything in between.

bucket of prawns lunch meal at Boathouse Balmoral Beach Sydney Australia

Stop for a snack at the Boathouse Balmoral Beach, Sydney, Australia. Photo: Tourism Australia

Dishes to try
The decadent, eight-texture chocolate cake by celebrated chef Peter Gilmore at Bennelong Restaurant, which is housed under the sails of the Sydney Opera House. Even if you don’t go in for the complete fine-dining experience here, you can pull up a seat at the bar to enjoy dessert in one of the city’s most iconic locations.

Sydneysiders love to brunch, and smashed avocado on toast is a popular order. At The Grounds of Alexandria, the smashed avo is served on house-made bread with tomatoes, ricotta, and an optional poached egg; wash it down with a “flat white” coffee, another local favorite.

Other dishes worth a detour: the freshly baked banana bread at the Boathouse Balmoral Beach, fish and chips at Icebergs while watching the surfers off Bondi Beach, Black Star Pastry’s strawberry watermelon cake, and Bill Grainger’s ricotta hotcakes.

group enjoying a picnic in the Cremorne Park in Sydney, looking over Sydney Harbour in Australi

Enjoy a picnic with Sydney Harbour views from Cremorne Reserve. Photo: Destination NSW

Prime picnic spots
Take a ferry to Cremorne Point, a grassy, waterside park on the northern shores of the harbor that boasts views of the city skyline, Opera House, and Harbour Bridge. After picnicking with the locals, enjoy a cooling dip in the harborside MacCallum Pool, or stroll along the Foreshore Interpretive Walk to gain an insight into the Aboriginal and early European history of the area.

Sydney’s newest harborside parkland, Barangaroo Reserve, is the perfect place to enjoy a late-afternoon picnic while the sun sets over the harbor. (It’s also become a popular vantage point from which to watch the New Year’s Eve fireworks.) If you’re keen to learn more about the indigenous history of this land, you can join one of the Aboriginal-led cultural tours, which explore the site’s rich Aboriginal history and cultural significance.

What to See and Do

Bondi beach panorama Sydney Australia

Don’t miss Sydney’s iconic Icebergs Swimming Club. Photo: Southern Crossings

Don’t miss
The Bondi to Bronte coastal walk takes in some of Sydney’s most popular beaches and spectacular scenic headland views. Start in Bronte and follow the path alongside golden beaches and quiet coves, past surf life-saving clubs, and over stunning rocky headlands—with an endless parade of locals in lycra and countless photo-worthy moments along the way. Head down early to enjoy a delicious breakfast at the locals’ favorite, Three Blue Ducks. Alternatively, stop for coffee at the Tamarama Cafe to watch the locals strut their stuff along the sands of the aptly nicknamed “glamourama” beach, or reward yourself with a casual lunch overlooking Bondi from the iconic Icebergs Swimming Club. Visit in late October or early November to marvel at the popular annual outdoor art exhibition, Sculpture by the Sea. If you’re feeling especially energetic, continue to Coogee for more stunning coastal views and golden beaches. The Waverley cemetery makes an interesting diversion, as it’s the final resting place of some notable Australians: former governors and Olympic gold medallists, aviators and authors, pioneers and poets. Reward yourself with lunch at the Coogee Pavilion.

Get a bird’s-eye view of the city with a helicopter or seaplane flight over Sydney and its waterways and beaches. For a truly breathtaking experience, add a detour to the pristine Ku-ring-gai National Park for lunch. You won’t believe that you are only minutes away from Australia’s largest city.

Views of the Sydney Harbour skyline from the Manly Ferry, Australia

Views of the Sydney Harbour Bridge from the Manly Ferry. Photo: Destination NSW

Cheap thrill
The Sydney/Manly Ferry operates between Circular Quay and the suburb of Manly, with its beachfront cafés, pier-side pubs, and quaint boutiques. Visitors and local commuters alike get out on deck with a camera during the 30-minute ride to capture the Sydney Harbour Bridge, Opera House, Garden Island Naval Base, Fort Denison, and the Royal Botanic Gardens.

Pylon Lookout. Though the Sydney Harbour Bridgeclimb is very popular, for a fraction of the cost you can view exhibits about the history and construction of the iconic “coat hanger” while climbing 200 stairs inside one of the massive stone pylons. Afterward, take the 15-minute walk across the bridge itself for great Sydney vistas.

When you need a break from the buzz of the city, grab some fresh air and stretch your legs on one of the many harbor foreshore walks. The Spit-to-Manly walk runs along waterside bushland tracks that showcase Australian flora and spectacular views. Get a glimpse of the local’s life as you pass by beautiful waterfront homes and bays filled with yachts of all shapes and sizes. Take a cooling dip in one of the many quiet coves, and reward yourself at the Manly finish line with a refreshing beer or a chilled glass of wine overlooking the harbor.

Contact Stuart

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Best Time to Go

Sydney’s summer months (December to February) bring beach weather, as well as festivals and harborside celebrations: Boxing Day sees the start of the Sydney-to-Hobart yacht race, followed by our world-renowned New Year’s Eve celebrations, and then the Sydney Festival a monthlong celebration of the arts culminating with Australia Day. (Remember that prices are also at their peak in summer, with stringent hotel booking conditions over the New Year period.)

Worst Time to Go

While the weather isn’t cold during the winter (June to August), it is not the ideal time to experience this alfresco city.

Biggest Rookie Mistakes

Assuming that Sydney can be explored in two to three days. In addition to its numerous cultural attractions, outdoor activities, beaches, and excellent shopping and dining, Sydney is surrounded by stunning national parks (including the UNESCO World Heritage-listed Blue Mountains) and Australia’s oldest wine-producing region, the Hunter Valley. Ideally, allow four to five days to explore the city and surroundings.

A tour of the iconic Sydney Opera House is on many visitors’ agendas, however the regular one-hour tour does not visit the backstage areas. This is only possible during the two-hour tour, which operates daily at 7 a.m. The backstage tour also includes breakfast in the “green room.”

Bragging Rights

Stuart can arrange a private surfing lesson with a seven-time world champion in the relaxed beachside suburb of Manly, or—for the ultimate foodie experience—a class with one of the masters of Australian cooking, Peter Gilmore (see “Dishes to try”).

Instagram Moments

For a classic Sydney Harbour view that incorporates both the bridge and the Opera House, it’s hard to beat Mrs Macquaries Point in the Royal Botanic Gardens. Go around sunrise for both the best light and fewest crowds.

Walk across the Sydney Harbour Bridge for some of Sydney’s best Intsa-opportunities. The views from the “other” side of the bridge at Bradfield park, or from the Milsons Point Wharf in front of Luna Park, offer panoramic harbor vistas and opportunities for creative angles of the Sydney Opera House, bridge, and city skyline. This is a perfect vantage point at any time of day, but especially at sunset and after dark for the city lights. The ferry ride back to the city (from Milsons Point Wharf to Darling Harbour or Jeffrey Street to Circular Quay) also offers some stunning photo opportunities.

Capture some spectacular shots of the sun rising out of the Pacific, bronzed Aussie surfers, the all-season Iceberg swimmers, and stunning coastal scenery along the Bondi-to-Bronte walk. Finish with an Instagram-worthy breakfast at the fabulous Three Blue Ducks café in Bronte. Stuart can arrange for a local photographer to accompany you and provide professional tips and insider knowledge.

The Souvenirs

Paddington Markets has long been an incubator for up-and-coming Australian designers of fashion, homewares, jewelry, arts, and crafts—much of which you won’t find anywhere else; it’s open every Saturday starting at 10 a.m.

Or head for the beautiful, grand old Victorian Strand Arcade. An oasis in the heart of Sydney’s modern center, the Strand houses a collection of speciality shops including several iconic Australian brands: delicious Koko Black and Haigh’s chocolates, Aesop skin care, contemporary jewelry and homewares by Dinosaur Designs, plus a number of Australian fashion designers.

Tipping Tip

Waitstaff in Sydney do not depend on gratuities for their income, nor are service charges routinely added; however, a tip of up to 10 percent in recognition of excellent service has become common in the better restaurants. Tip tour guides or concierges only when service has been exceptional. Taxi drivers and hotel porters appreciate a small tip, but no more than AU$1 or AU$2.

Airport Intel

A train service links Sydney Airport with the city. It is quick and efficient, with journeys taking 10 to 20 minutes, depending on the desired destination. A downside is luggage storage: Normal commuter trains are used, without convenient spots for international visitors to stow bags.


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