Day trips out of Sydney typically involve a 2-3h drive from Sydney center per way. There are many car rentals options; be it Hertz, NoBirds or East Coast Car rental. Car rental procedures are fairly easy to complete online and collection and return of cars will be clearly stated on the website. Do bring a GPS or rent one as navigating through Google Maps is quite tedious.

Within a 2h radius:

• Port Stephens: yacht marina, sand dunning and mountain climbing
• The Blue Mountains: a full day must be devoted to complete most of the major tourists spots like Wentworth Falls, Katoomba Falls, The Three Sisters, Scenic Railway, Orphan Rock and the Jenolan Caves (quite dangerous and long ride to Jenolan caves as roads are winding)

View from Princess Point on the Blue Mountains

 

View of the Three Sisters Katoomba

Katoomba Falls as seen from Blackheath Lookout Point



Area around the Jenolan Caves

Within a 3h radius: 

• Hunter Valley: basically an area with lots of vineyards belonging to the best Australian wineries. You can find Lindeman's, Rosemount, McGuigan's etc vineyards here. Do check online for vineyard tour timings. Unlike the American vineyards in Napa Valley where you pay for wine tastings, tastings in Hunter Valley are free but you'd be obligated to buy a bottle of wine.
• There is not much else to do in Hunter Valley besides wine tasting and the chocolate factory so do go with an open mind. 

McGuigan's Wines

Sydney being such a cosmopolitan city really offers a plethora of food choices; anything from Michelin starred restaurants to celebrity chefs like Jamie Oliver (Jamie's Italian) and the simpler, fuss-free road side meals.

Pancake on the Rocks (open 24h) with its delicious pancakes and Belgian Chocolate Praline from the Guylian Chocolate Cafe 


Mee Goreng and Nasi Lemak from Mamak Haymarket. This outlet opens at 530pm but has a snaking queue as early as 445pm. A plain prata costs AU$5.50 which is ridiculous by Singaporean standards (S$1 per piece?!)

Sydney is surprisingly easy to navigate with a GPS (get a SIM card from OPTUS at the airport. AU$2/day unlimited 3G and calls). Scoot now offers cheap air tickets from Singapore to Sydney (8h flight) and I do recommend paying $30 more for extra seat space. It's really worth it!

Here I'll recap my MUST DO-s in a quick list:

Sightsee

• Sydney Harbour Bridge (Circular Quay)
• Sydney Opera House (Circular Quay)
• The Royal Botanic Gardens (Walk from Circular Quay and to see Mrs Macquarie's chair)
• Museum of Contemporary Art (free entry)
• The Rocks Weekend Flea Market (Circular Quay)
• Darling Harbour (IMAX sydney - AU$26 with the 20% off coupon in the visitor's guide found in the airport)
• Wildlife Sydney (AU$25 if tickets booked online as compared to AU$30 at the door)
• Sydney Fish Market (fresh produce and sashimi)

Sydney Harbour Bridge and the view from within the Royal Botanic Gardens