Justin Timberland and Jessica Biel : $6.5 million – $9 million

For their nuptials on October 19, 2012, singer Justin Timberlake and actress Jessica Biel opted for total Italian immersion, renting out the entire ultra-luxury Borgo Egnazia resort in Fasano, Italy. To ensure absolute privacy from the paparazzi, the couple paid to close down surrounding roads and buildings, creating an impenetrable compound for their star-studded guest list. As Biel walked down the aisle, Timberlake provided the ultimate romantic soundtrack, playing the guitar and performing an original, unpublished ballad he had written specifically for her. The multi-day itinerary included casual pre-wedding beach bonfires and candlelit wine caves, cementing it as the gold standard for high-security Hollywood destination weddings.