The two actors were spotted having a day of fun in the sun, while enjoying the company of numerous gorgeous women - some of whom chose to ditch their bikini tops, reported E! online.
The duo were cruising across Sydney Harbour in Australia, after 38-year-old DiCaprio was asked to go back to the land down under to reshoot some scenes for Baz Luhrmann's The Great Gatsby.
Hill was photographed looking bewildered chatting up a topless sunbather on the deck. The 29-year-old Moneyball star broke up with his longtime girlfriend, Ali Hoffman (Dustin Hoffman's daughter), in September.