Kourtney Kardashian's boo, Travis Barker flies on an airplane for the first time since surviving deadly 2008 plane crash

On Saturday, the 45-year-old Blink-182 drummer flew on a plane for the first time since his deadly 2008 plane crash, which killed 4 people and left Barker with third-degree burns on more than half of his body.

As seen in photographs obtained by TMZ, Barker was joined by girlfriend Kourtney Kardashian as they headed to Cabo, Mexico on Kylie Jenner's private jet. 

The outlet reported that Kris Jenner and her boyfriend, Corey Gamble, were also on board. 

For the outing, Barker was photographed dressed casually, wearing a white tank top, gray pants with a black belt covered in metal studs, and a black beanie atop his head. Kardashian, 42, meanwhile, kept it cool in a black dress that she accessorized with a pair of black sunglasses. 

"It's a huge deal that Travis flew to Cabo. 

The plane crash many years ago was extremely traumatizing. He has needed a lot of help to get to this point," a source tells PEOPLE. "Kourtney has been very supportive. She never pushed for him to fly. They have managed to travel in the US without having to fly and Kourtney has been totally fine with it." Over a decade ago, Barker and longtime collaborator DJ AM (Adam Michael Goldstein) survived after their plane crashed shortly after takeoff as they were leaving South Carolina, where they had just played a show. Goldstein died a year later from a prescription drug overdose. 

The crash killed Barker's security guard Charles "Che" Still, his assistant Chris Baker, pilot Sarah Lemmon, and co-pilot James Bland, PEOPLE confirmed at the time. 

The musician had a long road to recovery, both mentally and physically after the accident. He suffered third-degree burns on 65 percent of his body and underwent several surgeries and skin grafts. Additionally, Barker was also dealing with "excessive" weed and prescription drug use. 

In June, Barker announced his plans to inch towards the skies again. 

"I might fly again," he declared on Twitter. Barker previously revealed in an interview with Men's Health in May that after Goldstein's death, he made the decision to quit using drugs and flushed medicine, "including stuff that I really needed," after his opioid tolerance started to rise with each surgery. 

"People are always like, 'Did you go to rehab?'" the drummer told the outlet. "And I [say], 'No, I was in a plane crash.' That was my rehab. Lose three of your friends and almost die? That was my wake-up call. If I wasn't in a crash, I would have probably never quit." 

In the same interview, Barker opened up about wanting to "make the choice to try and overcome [flying]," adding, "If I do it, and the angels above help me in my travels and keep me safe, I would like to come back and [tell my children], 'Hey, I just flew here, and then I flew home. And everything was fine.' I have to tell them, because I almost left them. That's a perfect day." The drummer also said that his fear of planes after the crash was once to the point where he recalled, "I couldn't walk down the street. If I saw a plane [in the sky], I was determined it was going to crash, and I just didn't want to see it." "The closer I was to it, it felt like I was closer to the bad stuff than I am to the good stuff. 

I felt closer to the experience of trying to escape, [to] being in an accident and being burned, trying to grab my friends from a burning plane," Barker added. 

Culled From PEOPLE