Went for a 9 day holiday recently to Sydney and surrounding areas. Documenting my itinerary for future reference :
Day 1: Arrival in AM @ Sydney airport. Drive to Jervis Bay.
Stay at Tranquility Beach House
Day 2 : Whale watch cruise, exploring the area
Day 3 : Hyams Beach. Drive to Bilpin, Blue Mountains (Farm stay).
Explore the farm Bilpin Springs Lodge
Day 4 : Jenolan Caves, Echo point look out
Day 5 : Scenic World, Blue Mountains. Drive to Hunter valley. Stay Hunter Valley Resort.
Hunter Valley Gardens Christmas Lights Spectacular
Day 6 : Horse riding, winery tour, wine tasting, shopping. Drive to Sydney
Stay The Sydney Boulevard Hotel. Dinner @ Chinatown
Day 7 : Walk to Opera House/Circular Quay (pass the botanic gardens)
Ferry to Manly Beach. The Rocks Night Market
Day 8 : Paddington Market. Attack of the Pirates boat ride.
Darling habour (Tumbalong water play area+ fireworks)
Day 9 : Darling habour (again! for the kids). Depart of Singapore in the afternoon.
My reviews of the places can be found on tripadvisor if you would like to know more :)