On Friday John Toshack takes his current side, Moroccan club Wydad Casablanca, to Egypt to face Zamalek in the first leg of their African Champions League semi-final.
Toshack was a legendary player for Cardiff City, Liverpool and Wales and, as a manager, won a Spanish league title with Real Madrid and led Swansea City from the bottom division to the summit of English football.
Now his Moroccan adventure is proving a successful sojourn in what the 67-year-old admits is the autumn of his sporting life.
After managing teams in the footballing outposts of Macedonia and Azerbaijan, Toshack is enjoying a new lease of life in Casablanca.
"I've been very fortunate in my career, but this one is something extra really," he tells BBC Wales Sport.
"If someone said you would be managing going on 68 I would never have thought so.
"It came out of the blue, it's another country and another continent and things are going really well."
After taking charge in June 2014, he led Wydad to the Moroccan title in his first campaign and followed that up with the runners-up spot last season to secure African Champions League football.
Toshack admits the foray into African football has come as a surprise even for a man of his formidable experience.
It has not just been footballing matters either. The Cardiff-born former striker has been left amazed by the vast distances he and his team have had to cover across the continent as they have progressed through the tournament.
And Toshack admits if his side were to lift the trophy next month, it would rank right up there with everything he has achieved in his career.
But although Friday's game is just the first leg of the semi-final - with the pair meeting again back in Morocco on September 24 - the former Wales boss has also hinted that lack of progress could see him bring the curtain down on his African adventure and perhaps his life in football all together.
"It's been very different and interesting," says Toshack.
"We've travelled to Egypt, the Ivory Coast, to Madagascar, to Zambia, in a competition which to win we have to play 16 matches. When we went to Zambia we were away for eight days.
"The (Morocco) Federation is good, we don't have to play for a week after a game, but it does cause problems.
"We are in September and not played a league game yet - we are already three games behind everyone else.
"To be honest, if we can win this, for various reasons it would have to go down as one of the most successful periods of my career. There have just been so many things we have had to adapt to.
"If things go wrong here, like they could easily do, I'm not sure I would have the patience again to turn things around.
"To be honest, we'll see how we do in these semi-finals and then that would be a good time to sit down and take stock."
Apart from his six years as manager of Wales, Toshack's two years with Wydad is his longest spell in a job since 2000.
Reflecting on his career which has seen Toshack hold 17 managerial roles with 13 different teams, it is the spell with Wales which has been subject to reappraisal.
In light of Wales' success at Euro 2016 and their progress under Chris Coleman and the late Gary Speed, Toshack himself is now being credited with helping to start the revival.
It was he who blooded many of the players who now make up the core of Coleman's side.
He handed debuts to Aaron Ramsey, Joe Allen and Joe Ledley and made Gareth Bale the youngest Wales international after selecting him aged 16 for a friendly against Trinidad & Tobago back in 2006.
"It's six years ago since I finished and to see so many of those players playing as mature professionals, it gives me a lot of satisfaction to be honest," Toshack adds.
"Looking at the Moldova game, what strikes me is the ease with which Wales win games now.
"I recall the difficulty we had just to get a result against these kinds of teams all those years ago. You can just see now how the players have matured.  Now you are winning a game 4-0 against Moldova, whereas before, whoever we played, that would have been difficult. "
Toshack insists Bale will go on to beat Ian Rush's goal-scoring record of 28 for his country and believes that, at one of his former clubs, Real Madrid, Bale has matured into more than just another player.
Bale's two strikes in the win over Moldova took his tally to 24 in 62 internationals.
"You would imagine he would break the record during this World Cup campaign, but if it does not happen now, it will sooner or later," said Toshack.
"Gareth's probably at the best age now to push on.
"I know they are delighted with him at Madrid, the way he plays, the ways he acts off the pitch and the things he says.
"On top of everything else he's turning out to be a terrific ambassador for his country too.
"It's not just Gareth, but a lot of the players with Wales. How many of them are up to 60 or 65 caps already? And they are only 26 or 27 years of age.
"There will be a lot of them breaking the record for Wales' caps."
The ancient Egyptian port of Alexandria has seen many historic events, and it might be about to witness the final throes of one of Wales' most illustrious sporting careers.