Winfrey, 56, hit the famous harbour's glittering waters on board the "Eagle Rock" with Crowe, a Sydney local, tailed by a flotilla of some 20 other yachts.
Wearing a white cap given to her by Crowe and emblazoned with the logo of his South Sydney Rabbitohs rugby league team, Winfrey beamed as she sat at the stern of the boat, talking sport with the "Gladiator" star.
"I'm having the time of my life," Winfrey said.
The harbour featured heavily on the megastar's weekend itinerary, with a glittering waterfront reception Saturday night, complete with fireworks, followed by a Sunday morning climb of the Sydney Harbour Bridge and a visit to Bondi Beach.
Australia paid 2.3 million US dollars to lure the talkshow diva Down Under -- mostly to cover accommodation costs -- but pundits claim the exposure could be worth more than ten times that amount.
Winfrey has been mobbed by fans across Australia, and was afforded a reception in Melbourne normally reserved for royals or rock-stars.
Russell Crowe Sails With Oprah
She will film a double episode extravaganza in front of 12,000 Australian fans in the Sydney Opera House forecourt Tuesday, with special guests to include Crowe, actors Hugh Jackman and Nicole Kidman and rock group Bon Jovi.
Rapper Jay-Z will also feature on the show, Oprah's publicists revealed Monday, with a "soaring finale" to star other "special guests" -- rumoured by local media to include rock stars U2, who are currently touring Australia.
The Oprah Winfrey Show said they received more than 350,000 requests for the free tickets, with the lucky 12,000 selected by ballot. The harbourfront precinct will be in virtual lockdown for the event, with street closures and police cordons.
So much footage had been gathered in Winfrey's whirlwind tour the show said it would now screen four episodes of her "Ultimate Australian Adventure" in January 2011.
Russell Crowe Sails With Oprah
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