Whether you're a fan of antiquing, slogging through kilometres of scribbly bushland or tucking into fish and chips in little beach side towns, it's never a bad idea to head south west of Sydney. Unlike some intra-state vaycays, much of the Southern Highlands is well serviced by train lines, so you can get there cheaply without a car.
With plenty of long, flat stretches, parts of the Southern Highlands can be a bicycle riders' paradise, the area is a camo-pattern of National Parks, so bushwalkers will be thoroughly satisfied. Meanwhile, the Illawarra region has some fantastic surf beaches. After you've worked up an appetite from all that activity, there are plenty of great dining options, from classic pub grub, to five star fine dining from the likes of Bowral's Biota.