Make Your Next Trip Extraordinary

Sydney, Australia: Insider’s Guide

by | April 28, 2022

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.

Expect trips orchestrated by Stuart to start at $1,000 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 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
Sean’s, tucked away on the northern end of Bondi Beach’s golden sands, is a long-standing favorite with locals and in-the-know visitors. Daily-changing blackboard menus showcase the freshest seasonal produce from land and sea. The tiny, simply-decorated 45-seat dining room, adjacent cocktail bar and, handful of outdoor tables enjoy ocean views and a relaxed Sydney beachside vibe.

Celebrated Australian chef Neil Perry’s newcomer to the Sydney scene, Margaret, has enjoyed a warm local’s welcome to become an instant classic. Named after Perry’s mother and in honor of her caring spirit, this Double Bay neighborhood restaurant exudes comfort and generosity, from the deep leather banquettes to the beautifully plated dishes. This is the kind of place where you can enjoy a perfectly poured martini or mouthwatering burger at the bar, or settle into the dining room to enjoy a feast of freshly shucked Sydney Rock oysters, Paspaley pearl-meat sashimi, wood-roasted vegetables, rotisserie chicken, Easter Rock lobster, and prime Wagyu beef.

Go for a long lunch in Sydney’s leafy Eastern Suburbs to sample chef Matt Moran’s delicious produce at Chiswick; the salad greens and fresh herbs are grown in the kitchen garden that the restaurant overlooks, and the lamb is sourced from the Moran family farm.

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, feta, zaatar, chilli, and an optional poached egg; wash it down with a “flat white” coffee, another local favorite. Alternatively, head to Sammy Junior for great coffees and toasted banana bread with the locals.

Enjoy a fresh fish and chips or bucket of prawns by the beach at the Boathouse Shelly Beach, just a short—and scenic—stroll from Manly.

For a sweet tooth indulgence on the go, sample Flour and Stone’s take on an Australian classic with their panna cotta lamingtons.

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.

Hidden away among magnificent waterfront homes on the Sydney Harbour foreshore, the grassy terraced gardens of McKell Park in Darling Point offer a leafy vantage point from which to enjoy a harborside picnic served with views that reach from the Harbour Bridge to the west, through to the Heads where Sydney Harbour opens to the Pacific Ocean to the east. This is a great spot from which to watch harbor festivities and activities such as the New Year’s Eve fireworks or the start of the Sydney to Hobart yacht race.

Across the harbor, Sydney’s Balmoral Beach is another prime picnic spot from which to watch the start of the Sydney to Hobart yacht race. Year-round, the grassy beachside lawns, picturesque rotunda, and the tiny island accessed by a small stone bridge provide plenty of places for a beautiful waterside picnic. The calm waters offer a family-friendly spot to cool off in the warmer summer months, and a collection of local eateries offer take-away picnic favorites from fish and chips to delicious fresh salads.

What to See and Do

Don’t miss
Exploring the city on foot. Sydney offers a collection of fabulous coastal walks and foreshore trails that provide an authentic window into the local lifestyle. The Bronte to Bondi 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. Stop for coffee at the Tamarama Cafe to watch the locals strut their stuff along the aptly nicknamed “glamourama” beach, or reward yourself with brunch in Bondi (Bills’ hotcakes are a long-time favorite, Speedos Café delivers Instagram content in spades, or grab a Lox in a Box bagel to eat by the beach). Visit in late October or early November to marvel at the popular annual outdoor art exhibition, Sculpture by the Sea. For those seeking a less well-trodden coastal walk, the Rose Bay to Nielsen Park walk takes in picturesque bays and harborside parklands perfect for picnicking, beautiful beaches, stunning waterfront homes, and iconic Sydney landmarks.

Seeing this sparkling harbor city from the water is a must—whether you choose to take the Manly Ferry or charter a luxury cruiser to soak up a slice of the enviable local lifestyle and explore the harbor’s hidden bays and beaches; but taking to the skies with a scenic helicopter or seaplane flight is also one of the best ways to really appreciate the beauty of the city built around a maze of waterways, fringed by golden surf beaches, and surrounded by pristine national parks.

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.

Head to the suburb of Eveleigh on a Saturday morning to visit the colorful Carriageworks Farmers Market. Chat with the farmers and passionate producers (who often include some of Australia’s most celebrated chefs) and sample their delicious wares, from artisan breads to boutique wines to traditional Indigenous bush foods to freshly shucked oysters. If your visit doesn’t fall on a Saturday, celebrated Australian chef and Carriageworks ambassador Kylie Kwong also has a new canteen-style eatery in nearby South Everleigh: “Lucky Kwong” serves Kwong’s famous Cantonese-style cooking incorporating locally grown Australian native edible plants (think caramelized pork belly with Davidson Plums or stir-fried local Warrigal greens) at very affordable prices.

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 and are looking for some indulgent downtime, take a short scenic seaplane flight over Sydney’s Northern Beaches to enjoy a long lunch either at Cottage Point Inn, on the water’s edge surrounded by the tranquility of Ku-ring-gai Chase National Park, or at Jonah’s, enjoying breathtaking views over Whale Beach below and the Pacific Ocean beyond.


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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 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.

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”).

Only Stuart’s travelers can spend a day with one of Australia’s preeminent wildlife researchers, venturing well beyond the tourist trail in the Blue Mountains to assist in important bushfire-recovery koala research.

Instagram Moments

For a classic Sydney Harbour view that incorporates both the bridge and the Opera House, it’s hard to beat Mrs Macquarie’s 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 Insta-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 Circular Quay, Barangaroo, or Darling Harbour) also offers some stunning photo opportunities.

Capture 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. 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. If you can’t find the perfect memento here or your visit doesn’t fall on a Saturday, the surrounding streets (Oxford Street and the Glenmore Street intersection particularly) also offer a great range of Australian brands, including Bondi Wash, Sarah & Sebastian, Dinosaur Designs, and a collection of Australian fashion designers from Aje, Bassike, and Camilla to Scanlan Theodore and Zimmermann.

Alternatively, 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 is expected.

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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