The couple are still overseas after helping the billionaire ring in her 22nd birthday on a yacht off the Amalfi Coast and decided to separate from the pack on Tuesday.
Holding hands while strolling through the breathtaking village of Portofino, Disick and Richie looked ready to seize the day couple style.
The "Flip It Like Disick" star kept it casual in a plain tee and colorful shorts. Adding loafers to the look, he seemed eager to get away with just his girlfriend.
Richie, who's 20 years old, sizzled with her outfit choice.
Rocking a white mini skirt with matching tube top, Lionel Richie's daughter made sure her vacation style was on point for their date.
The duo spent some time walking around the town and taking in all of the glorious sights it has to offer.
Portofino, known for its high-end boutiques and Instagram-worthy colorful shops, is definitely a celebrity destination.
Besides the KarJenners, big names like Mariah Carey, Tom Hanks, Madonna and Beyoncé have been known to invade the small fishing town.
Disick and Richie have been living out their little Italian dream for the past week, loading on a private jet from Los Angeles and landing in the beautiful Mediterranean.
Kylie celebrated her birthday in style on a mega-yacht with a select group of friends and family.
Richie has gotten close to Kylie in the past several months, even heading to Turks and Caicos with the billionaire for a recent all-girls getaway.
Their close relationship is probably a breath of fresh air for Disick, who shares three kids with Kylie's sister, Kourtney Kardashian.