Maurizio Zanfanti, dubbed the 'Romeo of Rimini', was getting intimate with the woman when he had a heart attack, according to local media.
Realising something was seriously wrong, the Romanian tourist alerted the emergency services, but the nightclub manager could not be saved.
Also known as 'Zanza', he died on Tuesday night "after doing what he did best - loving women", the Italian newspaper Il Resto Del Carlino reported.
Zanfanti, who is rumoured to have bedded more than 6,000 women in his lifetime, had reportedly known the tourist for a couple of years.
In the moments before he fell ill, he was having s-x with the woman in a car in Via Pradella, Rimini, in the country's Emilia-Romagna region.
Some reports claim the tourist was getting dressed when Zanfanti's illness became apparent, prompting her to alert the medical services.
Paramedics rushed to the scene, but the playboy passed away.
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