Penrith is usually just one or two degrees hotter than the average Sydney temperature. It is at the foot of the Blue Mountains and not far from Warragamba Dam which are good tourist areas. It is a big city and there are plenty of night spots for young people. Our cities are physically similar to yours. I went to school in Penrith and still enjoy the odd shopping trip back to the area. There is a direct train service from the City Centre out to Penrith. The time and cost of the journey depends on the type of train chosen. However, the fares are much more friendly than U.S.A. prices. If he jumps onto a Blue Mountains train it has fewer suburban stops before arriving at Penrith. However, I think half the fun is finding all of these things for himself. He should enjoy.