The 53-year-old X Factor judge hit the headlines this week over speculation that he has fathered a child with New York socialite Lauren Silverman.
But it appears he will be escaping the media spotlight for a few weeks by boarding his yacht and drifting around the south of France.
He was spotted leaving his Los Angeles home on Friday and being escorted by police to the airport, where he hopped onboard his private jet.
In what might come as a shock to Lauren, Simon will be surrounded by his ever-present circle of women – many of whom are exes of the mogul.
Sinitta and former fiancée Mezhgan Hussainy are expected to be keeping him company in St Tropez when he arrives.
Married Lauren is said to be around ten weeks pregnant and is reportedly being divorced by estranged husband Andrew Silverman – formerly a close friend of Cowell – over the affair.
Simon's representatives have yet to confirm he is the father of the child, but Rosy Davis, the stepmother of Lauren, appeared to bolster the claims last Wednesday.
"We are all excited for the baby," she told reporters.
"Any kid is a blessing."
Yesterday evening (Saturday 3rd August), Simon was spotted in Las Vegas watching his band One Direction in concert.
He acted as cool as a cucumber as he attended the gig with a male friend, despite the legions of audience members armed with camera phones.