With views over Sydney Cove and Walsh Bay, the Rocks are a very central area where entertainment, cuisine, and great views over the water converge. In the few blocks between Cumberland Street and Circular Quay West, you'll encounter a ton of pubs and “hotels” for your late night rendezvouses and AFL-watching excitement, while the full compliment of trendy restaurants will be at your disposal. On Cumberland alone there are three excellent staples of both nightlife and cuisine: the Australian Heritage Hotel (big for backpackers and kangaroo pizza), the Glenmore Rooftop Hotel (don't miss the Sydney Harbour view), and Harts Pub (arguably the best spot in Sydney for craft beers).
One of the most popular tourist areas in the city for the views of iconic landmarks like the Sydney Harbour Bridge and the Sydney Opera House, it's worth enjoying this gentrified district for more than expensive meals or drinks with a view. There are also a parade of historic buildings that include Cadmans Cottage and the waterside Dawes Point Battery in which to indulge your sense of culture.