Despite its dense urbanisation Sydney is still wild at heart and heaven for walkers. The city’s signature walking trail is the Bondi to Bronte, a dramatic coastal walk through blue-chip beachside suburbs. On the north shore, the 10-kilometre Spit Bridge to Manly Walk offers equal awesomeness without the crowds.

Ku-ring-gai Chase National Park shelters one of the largest concentrations of First Nations engravings on the continent. Guringai elder Laurie Bimson leads three-hour tours into the bushland to decipher this extraordinary “giant road map” marking food sources, marriage, initiation and education sites and gathering places. He’ll even teach you how to throw a boomerang.

The 42-page wine list at Dear Sainte Eloise, the Parisian-esque Potts Point wine bar and restaurant, offers around 400 vintages from Georgia to the Jura, as well as from our own backyard. There’s more French-style bistronomy at nearby Bistro Rex, which serves classic dishes of Wagyu tartere, kingfish ceviche and steak frites.

Hire a kayak from Rose Bay Aquatic and set a course for Shark Island (Boowambillee) in the heart of the bay to swim, explore and marvel at the Port Jackson panoramas. Pack a picnic or follow the foreshore to local favourite, Catalina, for Mediterranean-inspired fare with an Australian twist – including Sydney rock oysters, Abrolhos Island scallop crudo and Moreton Bay bug lasagne – served with a side of views.

Learn how to capture the city’s best angles on a photo shoot with the Sydney Photography Group. Regular small-group guided walks teach everyone from beginners to pros how to harness the light and spirit of Sydney in two and three hour shoots in central CBD locations such as Hyde Park, Observatory Hill and Opera House.

On Wednesday nights, savvy art lovers come to worship at the Greek temple-inspired Art Gallery of New South Wales and its ultra-modern new extension. It’s the one night of the week when doors stay open till 10pm, and visitors can indulge in talks and events, drinks and food, and the gallery’s expansive collection.

Make like a movie star and hire a superyacht for the day from Sydney Harbour Exclusive, where fully crewed vessels accommodate anywhere from two to 100 guests. At the budget end of the spectrum, DIY in a two-person red speedboat, touring in groups of no more than six, with a guide leading the way.

Experience the unique Sydney thrill of semi-wild swimming at sea baths such as Wylie’s and Giles, both in Coogee. Wylie’s, just south of the main beach, offers daily yoga and Pilates classes onsite – be sure to book ahead to secure your spot. Further north at Freshwater Beach, the Freshwater Rockpool is tucked below the Freshwater Lookout and is ideal for a post-hike dip to cool off.

Crown Sydney at Barangaroo offers a suite of lavish dining experiences in the heart of Sydney. Chief among them: Alessandro Pavoni’s a’Mare, for impeccable Italian; Woodcut, for prime cuts of meat and fish; and Oncore by Clare Smyth, the first international outing by the three-Michelin-starred British chef.

Most Blue Mountains tours tick off the main tourist draws; Paul Hartmann prefers to explore the hidden beauty spots of his World Heritage-listed backyard. His private, day-long outings will stop for morning tea to admire the famous spectacle of The Three Sisters, but then he’ll take guests off-road to find lesser-known treasures.

For a classic Sydney day out, jump on the Watsons Bay ferry at Circular Quay, ogling waterfront mansions along the way. From the terminal, wander the colonial streets to Camp Cove Beach and along the South Head loop to the candy-striped Hornby Lighthouse, perched above a surging Pacific.

Lyne Park at Rose Bay, the site of Sydney’s first international airport, keeps tradition alive with scenic seaplane flights over the Emerald City. Strap in for 15- or 30-minute air safaris with bird’s-eye perspectives of the Opera House, Harbour Bridge, Bondi Beach and the colourful Sydney coastline.

Discover’s Sydney’s bohemian side at The Old Clare, an old brewery reborn as character-filled 69-room hotel with handsome heritage features and an upcycled luxury vibe. On-site attractions include an Art Deco-era pub, a rooftop bar and pool, and refined eating in the suitably industrial-chic surrounds of the new seafood-centric Longshore.

With more than 100 to choose from, there’s a beach to suit every mood. For celebrity spotting, head to Palm Beach. Balmoral’s perfect for picnics or leisurely lunching at harbourfront restaurants. For boardriders, Avalon and Manly rarely disappoint. For sunset swims, west-facing Shelly Beach is hard to beat.