The Flip It Like Disick star, 38, was seen exiting a Hollywood bar on Saturday, seemingly going incognito in a baseball cap and sunglasses worn with a hooded sweatshirt.
Scott looked downcast while waiting at the valet stand at 1:11 AM in photos obtained by Daily Mail just before he jetted off to a sunny destination the following day.
"Where to? Next stop, the beach!" he captioned an Instagram Stories post showing himself aboard a flight and looking out at the tarmac.
Last Thursday, the Talentless CEO was also seen hanging out with Rod Stewart, his son Sean Stewart and daughter Kimberly Stewart while grabbing a meal at LAVO Ristorante in West Hollywood. An onlooker told E! News that Scott "seemed in good spirits."
Interestingly, the Stewarts introduced Scott to the Poosh founder, 43, many years ago.
This weekend, Kourtney and Travis, 46, were surrounded by fellow celebs, friends and family as they prepared to exchange vows in their most lavish ceremony yet held at 16th-century Castello Brown in Portofino on Sunday.
Kourtney and Scott's three children — Mason, 12, Penelope, 9, and Reign, 7 — were all in attendance, as well as Travis' kids with ex-wife Shanna Moakler: Landon, 18, Alabama, 16, and stepdaughter, Atiana De La Hoya, 22.
Penelope and Reign served as the flower girl and ring bearer while Atiana and Alabama were bridesmaids.
Neither of the exes attended the star-studded Italian nuptials, marking the couple's third time since marrying at One Love Wedding Chapel in Las Vegas on April 4 as well as at a courthouse in Santa Barbara last Sunday.
"I wasn't that caught off guard," Scott said about Kourtney's 2021 engagement on the May 5 episode of Hulu's The Kardashians. "I thought that they'd already be married [from] the way that she was talking. It wasn't crazy," he told Khloé. "Thank God, because at another time in my life, if I'd heard that, life would've been over for me."