By Sea, by Sky, by Land, by Wine | 24 Luxurious Hours in Sydney, Australia

Upon descending into Australia, there’s nothing more exciting than a window seat – allowing your inner-child to release as you gaze below, marvelling at the magnificent trio of Sydney Harbour, Sydney Harbour Bridge, and Sydney Opera House.

Within Australia, embrace that inner-child spirit: explore, be inquisitive, absorb the magic of Australian culture. Beyond that iconic trio there is depth to Sydney – a vibrant and constantly evolving city. Let yourself be guided by local wisdom with days that seamlessly flow in the most exquisite harbour city in the world.

Here’s 24 hours of the sights and sounds of Sydney with a splash of luxury and style.

Lose yourself within The Rocks District – the birthplace of Australia. In May of 1787, 11 ships and 1,400 passengers (roughly half convicts) left Portsmouth England, arriving in The Rocks District on 26 January 1788. Sydney Harbour was described as “beautiful, thick bush and rock landscape” extending to the water’s edge. The land (home to the Gadigal people) was mostly covered in dense vegetation and rocky terrain.

Today The Rocks is filled with weekend markets, historic pubs, and opal shops… but walk slowly and hear stories of convicts like Elizabeth Hayward who stole clothing at the age of 13 – her punishment being the journey to Australia as a member of the First Fleet… and James Squire who received “150 lashes” (now a popular beer brand) for stealing ingredients to brew beer… Stroll through hidden, cobblestone laneways to soak in the culture and architecture of Australia’s origin.

Coast past Sydney Opera House and arrive at Sydney’s oldest airport where champagne pours during check-in for an unforgettable 15minutes Sydney Seaplane flight. As you soar from Rose Bay Terminal, you will marvel as Sydney Harbour forms beneath you… sandy beaches, National Parks, and views to dozens of beaches. The returning scenic loop is magical as you fly directly over Sydney Harbour Bridge and Sydney Opera House before descending back at Rose Bay Wharf.

Stepping out of your Sydney Seaplane, a Sydney Water Taxi awaits to showcase 90 minutes on lively Sydney Harbour – glide past sailing races, our endearing ferries and party boats, perhaps spot a seal, dolphin, or harbour penguin. Watch locals kayak and SUP where whales pop in for a sheltered rest from their Antarctic journey.

Cruise past glamourous suburbs such as Point Piper and Vaucluse… take in views at secluded beaches such as Milk Beach and Kutti Beach… then “escape” Sydney with a quick journey under Spit Bridge for a taste of the posh-and-peaceful area known as Middle Harbour before arriving at Manly Beach.

“Seven Miles from Sydney and a Thousand Miles from Care” lies Manly Beach, Sydney’s most charming beach suburb. As the crow flies, Manly Beach (named after the First Fleet opined on the manly looking Aboriginals) is only 11kms from Sydney Opera House, but it is mind-soul-body away from city life. Home to 17,000 Sydneysiders, Manly is a bustling suburb yet paradisiacal oasis as it blends bars and restaurants through its local beach and surf culture with hiking trails that cross onto deserted beaches within magnificent National Parks.

Start with lunch at Hugo’s Manly, a Sydney institution that has perfected al fresco dining on the water with harbour views and delicious Italian-Aussie cuisine besides a cocktail and wine list to match.

A 30minute meander to Shelly Beach is the perfect way to burn off lunch. Water dragons bask in the sun, and nearby fit beach bodies tan on the rocks beside the idyllic Fairy Bower Rockpool. In the distance is a variety of splendid beaches that make up Sydney’s Northern Beaches, and above the trail lies multi-million dollar mansions reminiscent of the Italian Riveria.

Enjoy a ride back to Circular Quay with Sydneysiders on the “Most Beautiful Ferry Ride in the World”. Pair it with a wine or beer as you pass picturesque harbourside homes, National Parks, and of course Sydney Harbour Bridge and Sydney Opera House.

Steps from disembarking the ferry is Customs House – opened in 1845, it served as the primary entrance into Sydney for goods and people for well over 100 years. Walk on the glass floor within as an iconic model of Sydney lies below, offering a bird’s eye view of the CBD.

From there, explore the labyrinth of laneways around Establishment Sydney and Ivy Precinct… stand under a photogenic sculpture of Sydney’s lost wildlife called “Forgotten Songs”. Pop out at Martin Place, now Sydney’s financial hub but once a fresh flowing river of water and the primary reason the First Fleet settled in The Rocks District. Explore Sydney’s historic Post Office which spills out onto Sydney’s main shopping district called Pitt St Mall.

Westfield Sydney (founder Frank Lowy is a rags-to-riches Sydney story) is home to well-known brands such as Chanel, luluLemon, and Hugo Boss. Just steps away and built in 1898 is a vast and angelic structure filled with cafes and similar brands: The Queen Victoria Building. Yet the finest gallery oozing charm and Parisian style was constructed in 1891 – The Strand Arcade – with hammer, nails, and leather the lads love Andrew McDonald’s bespoke crafted shoes and boots while fashionistas delight in shopping at Australian brands Camilla and Marc, Scanlan Theodore, and Bassike.

Under a shining sun, Sydney is the ultimate “beer at a beach bar” culture. Yet after sunset? It’s time to find something cool, hidden, and uniquely Sydney. Two floors below sea level lies The Caterpillar Club – the perfect sanctuary to raise a glass after an active and luxurious day on Sydney Harbour.

Behind the bar is an enormous vinyl inventory – the largest record collection in the Southern Hemisphere. On any given night, there might be live jazz or slick lounge tunes spun by a DJ… Caterpillar Club is stylish, it’s relaxed, and it’s a throw-back in time that requires an Old Fashioned or Manhattan as your surroundings transport you to an episode of Mad Men.

Sydney’s food scene can be described as dynamic, diverse, and delectable – a foodie’s paradise. From beach views to sunsets overlooking Opera House views… from swish rooftops to swanky basement joints, there’s a destination and cuisine for every palate. Some highly rated establishments certain to tickle your taste buds are:

• World-class rated with Sydney Opera House views / degustation at Quay;
• Lux and local on the water at Otto Woolloomooloo Wharf;
• Colonial Hong Kong ambiance underground at Mr. Wong’s;
• View over Bondi Beach at Iceberg’s Dining Room and Bar;
• Neighbourhood vibes and local dining at Ursula’s Paddington; and
• Swanky and hip in Surry Hills at Porteño.

Upon waking, you’ll think the past 24hours was a dream. I’d say: It’s only the beginning of exploring the most beautiful city in the world. Waiting is a day trip via chauffeured vehicle or helicopter to The Blue Mountains, Hunter Valley, or Southern Highlands. A tour and performance at Sydney Opera House. The views and heart-raising experience of Sydney Bridge Climb. A full day on a luxurious yacht on Sydney Harbour. And Sydney’s best kept secret? 100 kilometres of coastal walks and hikes to choose from with secluded beaches, breaching whales, and Sydney Opera House views just in the distance – including lobster and champagne lunch to refuel.

The hardest part is leaving Sydney. As months pass memories might fade, but like a boomerang they return with another journey to Australia.