Southern Highlands (New South Wales)
 is located southwest of Sydney in New South Wales, Australia. 
The Southern Highlands is within commuting distance of Sydney and is popular for weekends away from Sydney. It is a cooler climate than Sydney. It has more identifiable seasons than Sydney, with a cooler spring, and leaves falling in autumn.
The district can be reached by train from Sydney and by car via the Hume Highway. Allow 80 minutes to travel by car from Sydney to Bowral unless driving on a weekday afternoon when an additional 30-45 minutes will be needed. Friday afternoon traffic can be particularly bad. A regular mini-bus shuttle service  from Sydney Airport is also available.
Trains run on NSW Transport's South Highlands Line between Campbelltown and Moss Vale (and occasionally on to Goulburn) approximately once every two hours. Long-distance trains also stop at Moss Vale, with some services also stopping at Bowral, Mittagong and Bundanoon.
Private car is the easiest way to travel around the villages of the Southern Highlands. The region has a taxi service  and a local bus company , which also connects to Nowra allowing access to the South Coast.
Otherwise, Berrima Buslines runs bus services from Moss Vale to the surrounding towns and villages, or you can take the train to major towns like Bowral and Mittagong (see above).
Cycling around the many country lanes and national parks can be a pleasant way to see the area.
There are also several wineries in the area which serve food.
Short diversions off the main freeway from Sydney can give a much more pleasant and tasty place to eat than the highway services.
There are country pubs in Bundanoon, Sutton Forest and Berrima. There is more serious nightlife in the larger towns of Bowral, Mittagong and Moss Vale. The Bowral scene is more upmarket, and caters more for the tourist traffic. The Moss Vale pubs by contrast seem a little smaller & friendlier, catering for locals & tourists.
The Southern Highlands is generally a safe area. Beware of some alcohol fueled violence in the larger towns, like Moss Vale. Many of the roads in the area can be narrow and sometimes unsealed. There can also be cyclists and pedestrians walking on the roads.
If you are travelling on to Sydney, consider taking the Illawarra Highway from Moss Vale over the Macquarie Pass via Robertson and Wollongong, with spectacular winding mountain roads, and coastal views, and only adding 30 minutes or so to the trip to Sydney.