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Sydney, Australia: Insider’s Guide

by Stuart Rigg | September 6, 2014

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 $560 per day for two travelers.

Where to Stay and Eat

Best bang-for-your-buck hotel
The recently fully refurbished Langham Sydney offers secluded tranquility only moments from the popular restaurants, galleries, and markets of Sydney’s historic Rocks precinct. The rooms are the largest in the city—all with windows that open, many with harbor views—and the hotel also has a range of dining options and a world-class spa and health club. I can arrange for daily complimentary full breakfast for two and an upgrade to the next available room category.

Restaurants the locals love
Fratelli Paradiso is an ever-popular Italian restaurant in the hip suburb of Potts Point. No reservations and no individual menusbut the waiters offer a full explanation of the seasonal dishes. Don’t miss the signature fried calamari!

The Boathouse Balmoral Beach is the perfect place for a morning coffee by the water’s edge or a classically Sydney lunch of a bucket of fresh prawns while watching Sydneysiders at play. The relaxed and beachy setting, with indoor and outdoor tables at the end of the sand in Middle Harbour, is popular with locals for breakfast, lunch, and everything in between.

Must-have dish
Few locals would argue that an absolute must while in Sydney is breakfast or brunch at Bills for his ricotta hotcakes, served with banana and honeycomb—indeed, some say they warrant their own entry on the Australia Day honors list (usually reserved for deeds that benefit the nation!). There are two Sydney locations; my preference is the original Bills in Darlinghurst, which is just as sunny, casual, and infectiously fun as Bill Granger himself.

Ferries in Sydney Harbour, Australia

Ferries in Sydney Harbour. Photo courtesy Tourism Australia.

Prime picnic spots
Opened to the public in September 2015 for the first time in more than 100 years, the Barangaroo Reserve is a perfect place for a harborside picnic and foreshore walk. Head down in the late afternoon to watch the sun setting over the harbor. 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.

Head to Parsley Bay on the water’s edge of Sydney’s Eastern Suburbs to picnic with the locals. Tucked away between some of the city’s most expensive residential streets, Parsley Bay offers a tranquil swimming beach, with a suspended wooden footbridge spanning the bay as a focal point. Walk off your lunch to discover quiet waterfalls and native water dragons lazing in the sun. The Parsley Bay kiosk sells coffee, ice cream, snacks, and light lunches for those who don’t wish to pack their own picnic.

What to See and Do

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.

Andrew (Boy) Charlton Pool. Largely frequented by residents, this saltwater public pool has a stunning location, set on the harbor between the Royal Botanic Gardens and the Garden Island Naval Base. There’s also a very good café with a great view, and sunbeds for lounging.

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, Sydney Harbour Bridge

Pylon Lookout, Sydney Harbour Bridge. Photo courtesy Tourism Australia.

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.

Jump on a ferry to Watsons Bay, enjoying the views as you approach the southern entrance to Sydney Harbour. Once a tiny fishing village, Watsons Bay now offers walking tracks, beaches, and a lovely harborside park. Doyles Restaurant is famous for seafood, but you can also pick up take-away fish-and-chips from the kiosk. On Sundays, families enjoy greatly reduced fares on Sydney’s network of ferries and trains.

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Best Times 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

Following a private tour of the Sydney Opera House, meet with an Opera Australia vocal coach who has toured and worked with many world-renowned performersincluding the legendary Dame Joan Sutherland, one of the most remarkable female opera singers of the twentieth century. You’ll have afternoon tea in the coach’s home and marvel at her many behind-the-scenes stories.

Instagram Moment

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.

Perfect Souvenir

It can be a challenge to source locally made souvenirs, which is why I love Paddington Markets, open every Saturday at 10 a.m. There are more than 150 stalls of Australian-designed and -produced arts and crafts, much of it not available anywhere else. I particularly like Ricardo’s Pewter.

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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The trip went flawlessly!

Jacquie Yannacci | October 25, 2018
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