Luke Hall, 18, was a passenger in the rented open-top 4x4 being driven by Zara Crane-Davies, 40, when it hit a kerb, rammed into a motorbike and collided with a wall.
Zara Crane-Davies made history when she was in jail after being involved in the UK's first ever lesbian prison wedding.
The vehicle she was driving careered off the road and landed in an empty field in Crete, instantly killing Luke and Crane-Davies, an inquest at Bradford Coroners' Court heard.
Another passenger, Louise Waddington, 39, who was living with Crane-Davies, suffered severe injuries, while an unidentified 18-year-old man escaped the crash unhurt.
Speaking at the inquest, Luke's "devastated" mother Anne Hall said she couldn’t excuse herself for letting him go away on the trip.
She had hauntingly told Luke to "stay safe and come home in one piece" in a Facebook post before he went on the holiday.
She told the court: “It’s just absolutely devastating as a family. It was the first time he’d ever gone on holiday on his own, and I will never forgive myself – I wish I had talked him out of it.”
The crash took place on the final day of the apprentice joiner’s two-week island getaway, at 6.05am.
The apprentice builder from Dewsbury had flown out to the island with three pals for the trip and was said to be in constant contact with his parents.
The inquest heard how he had met the two women in a club in Malia, between the evening of July 7 and the early hours of July 8, 2019.
He was travelling back to their Stalida apartment in the rear seat of the car when the crash occurred and was pronounced dead at the scene.
Following the incident, a post-mortem examination conducted by a Greek pathologist listed his cause of death as a fatal injury to the “cross-section of the stem neck”.
Clarifying these comments, senior coroner Martin Fleming said Luke may have suffered a possible “trauma to the brain” or a “fatal spinal injury”.
He added that he would have passed away “so rapidly that he wouldn’t have known in the moment.”
An inquest into Crane-Davies' death, held earlier this year, heard she was found to have amphetamines present in her system at the time of the crash.
Senior Coroner Nigel Meadows said then that there was inconclusive evidence to suggest if the amphetamines in Crane-Davies’s system contributed to her death.
While agreeing with the findings, Mr Fleming said the drugs may still have contributed in some way to the incident.
He said: “I take cognisance of the fact that she did have drugs inside her and they must have played some part in the incident.”
Two years on, Mr Fleming said the teen's parents were still trying to come to terms with the loss of their son.
His mother, in particular, broke down as she described his character, hopes for the future and past achievements at school.
She added: “He was liked, he was honest, he was funny and also loving. He worked from being 15 years old. He was very good at school. He was so intelligent. He left school and went to one interview and got the job. He just loved working hard and getting his own money.
“He got an apprenticeship. He was planning to be a joiner. He wanted to have his own business. He even specified how many children he would have. He was going to get married. He would have been an amazing father – that’s just the kind of person he was.
“He loved his football – he was captain of the football team. He kept himself fit, and he was never in trouble with the police. He didn’t do drugs. I couldn’t have asked for a better son.”
Luke had opted to go on the holiday with three pals instead of a tour with his team, Dewsbury Rangers Amateur Football Club, to Germany.
His teammates were said to be “heartbroken” when news first broke of his death.
Recording Luke's death as resulting from the injuries that he sustained in the road traffic collision, Mr Fleming said that it was clear he had touched many lives.
He said: “Luke was a much-loved son, brother and grandson. He touched the lives of many. He was amazing, he was funny, and he came from a close family. He was a young man with aspirations and goals. He was embracing the life that he had.”
It was recorded at the inquest into Crane-Davies’s death that she also passed away as a result of the road traffic collision.
She was previously convicted of murder in 2003 after she fatally stabbed her neighbour, David Thompson, 37, following a row.
When she was in jail, she made history by being involved in the first-ever lesbian prison wedding, marrying convicted drug dealer Joanne Crane-Davies, 46, in February 2010.
She later became a successful entrepreneur as director of Social investor CIC, and in 2018 was named Mentor of the Year at the Northern Power Women Awards.
In 2019, she was named Chief Operating Officer of the Resume Foundation, which helps marginalised individuals to find work.