Wightlink Leading Rating Mark Mitchell stepped up to help Hilary Spinks, 70, who had crossed the Solent on an early FastCat from Ryde.
She was due to board a coach in Portsmouth, but didn’t make the connection after 'underestimating' her transfer time.
The former boarding school matron, who had been looking forward to her ‘turkey and tinsel’ trip to Halifax, returned home in tears.
That was when kind-hearted Mark came to the rescue - offering to personally drive the pensioner 260 miles north to her hotel in Halifax.
After his shift ended, he went home to collect his car before then hitting the road for the five-hour journey.
Mark, who lives on the Isle of Wight, said: ‘My heart melted when I heard Hilary had missed out on her holiday as it had already been cancelled twice because of Covid. We had chatted about it during the sailing to Portsmouth and I was upset to hear she was going home instead of enjoying herself in Yorkshire.
‘I thought of how my elderly relatives would be disappointed, if it happened to them, and wanted to put things right for her.’
The pair stopped off for refreshments along the way, and Mark’s round-trip was a whopping 520 miles.
Hilary was stunned by Mark’s kindness. Speaking of the drama, she added: ‘I underestimated the time it would take to walk from the terminal to the pick-up point.
‘By the time I had even got out of the station and saw what the time was it was clear I had missed it. I felt terribly upset and also annoyed at myself.
‘I really look forward to these holidays and I was so disappointed and sad at the thought of having to turn around and make the journey back home.
‘When I got back to Wightlink, they came to see what was wrong. I told them what had happened and it was then that Mark offered to drive me.
‘I couldn’t believe it. It was such a surprise and I just didn’t think someone so young would do that for someone of my age.
‘Wightlink staff are always good to me but what Mark did was amazing. He was so kind and thoughtful and I am very grateful.’
Keith Greenfield, Wightlink chief executive, said he was ‘delighted’ to hear of his employee’s actions.
‘Not surprisingly, Mark has won our monthly award for colleagues who go the extra mile to help customers,’ he added. ‘Although we have many wonderful members of staff, not many have gone quite this far.’