How best to spend 48 hours in and around Sydney

With its spectacular harbour, gorgeous beaches, surrounding national parks and world-class restaurants, few places compare to Sydney. We suggest our clients begin their trip with a few days here to recover from their jet lag, to enjoy the city’s many treasures and to get ready for their Australian adventure.

I was fortunate enough to live in Sydney for a year and a half, and can vouch that there is so much to do, which makes it very difficult to narrow it down to just 48 hours. However, we have outlined below a fun and varied way to spend two days in the city. Of course, in reality, everything is completely flexible and we can hone your itinerary endlessly, depending on your interests.

Day 1

Your insider guide will collect you from your hotel and take you to Mrs Macquarie’s Chair for a wonderful, panoramic view of the city, Sydney Opera House and Sydney Harbour Bridge. This is the perfect spot for your guide to point out some of the highlights and set the scene.

Next, you will be driven through Paddington, an older neighbourhood where the streets are lined with pretty terrace homes and leafy trees, en route to Coogee. Australians love their coffee and, in this laid-back coastal suburb, in my opinion, the best place to go is Barzura. This is a great place to kickstart the day, take in the vistas of the broad, sandy beach and watch the surfers crash over the waves.

A wonderful way to enjoy the coast is to set off on a 6km walk from Coogee to Bondi. This takes about two hours and features stunning views, beaches, parks, cliffs, bays and rock pools. Along the path, at Bronte Beach, we will arrange for you to meet Tim Ella, an aboriginal guide from the Dharawal people who grew up embracing his culture and learning the ways of his ancient ancestors.

A knowledgeable and brilliant storyteller, Tim will recount tales of his people. In the past, this little beach would have provided plentiful food for the local tribes, and he will point out the spots where, in years gone by, they would have dived into the ocean to spear fish and lobsters, and collect abalone and other shellfish. In the gully, there is a little brook that, for thousands of years, provided fresh sweet water. Being with Tim is fascinating and brings bygone era to life.

During his school holidays, Tim used to go ‘walkabout’ with family and friends, camping up and down the east coast, from Newcastle in the north to Eden in the south. But never once did he forget his origins. Now, he is a highly respected teacher of the Yuin people and an Aboriginal guide, wishing to share all he knows with visitors. You can sip a bush tucker morning tea with him, before continuing to Bondi Beach.

At Bondi, it’s time to hit the waves. A private surf lesson is certainly one of the most exhilarating experiences in and around Sydney. I used to recommend this to all my friends when they visited. We know the best local instructors, so, no matter what your skill level is, you will be in safe hands. In my view, there is nothing better than experiencing Aussie beach culture from a board on Bondi Beach.

Afterwards, you’re bound to be hungry, so I would suggest strolling along the promenade to Porch & Parlour, one of our favourite Bondi lunch spots, where the dish to die for is smash ‘n’ hash (potato rosti with a poached egg, hollandaise, yucatan onion, house relish sautéed greens and bacon, salmon or haloumi). Then walk to Gelato Messina Bondi, which serves quite possibly the best ice cream in Australia! If you’re an art or photography enthusiast, a fun stop-off here is the nearby gallery, Aquabumps, where you can browse fabulous aerial beach photographs, before jumping back into the car to head north to Watsons Bay for a refreshing drink as the sun sinks into the ocean.

Back in Sydney that evening, we recommend dining  at one of the city’s many fantastic restaurants. One of my favourites is Firedoor, which is located in the suburb of Surry Hills. The chef, Lennox Hastie, has recently been named Citi Chef of the Year in Australia’s Good Food Guide Awards.

Day 2

On your second morning, your guide will take you e-biking along the Sydney Harbour foreshore and to the historic Rocks in the inner-city neighbourhood, Barangaroo, where you can stop for a delicious coffee at Micro by Coffee Alchemy. From there, it is an easy ride up to Observatory Hill and over Sydney Harbour Bridge to the lower north shore. Here, younger children might enjoy a ride at Luna Park, where you can also discover Wendy Whiteley’s Secret Garden.

Wendy’s husband was the late Brett Whiteley, a renowned artist. They lived here in Lavender Bay for two decades and Brett painted many of his iconic Sydney Harbour pictures in their home. Following his death in 1992, his grief-stricken widow began to clean up the land-filled valley at the foot of her house. Once she had cleared the site, she began to create a garden like a giant painting. Rather than being horticulturally inspired, Wendy’s gardening is driven by aesthetics, colour, form, beauty and whimsy.

Credit: Jason Busch

Leaving the e-bikes, you will then climb aboard a fast rib to zoom through the Harbour and out into the Pacific Ocean, where – if you are travelling between May and November – you will ride among humpback whales as they migrate north, an incredible experience. Your rib will drop you at Manly Wharf for lunch at Hugos, which lies in a stunning waterfront location and serves scrumptious, Italian-inspired seafood dishes and amazing pizza.  Afterwards, if you feel like it, you can wander across to Manly Beach and along the promenade, before returning to the city in a water-taxi or aboard the famous Manly Ferry.

Credit: Hugos Manly

To top of your time in Sydney, on your last evening, enjoy a pre-theatre dinner at the two-hat restaurant, Bennelong, under the sails of the Sydney Opera House, before attending a performance. If you’re wondering what I mean by ‘hatted’, please note that Australia is yet to be recognised by the Michelin-star system but their equivalent is ‘hats’. Strange but true.