Alan, who worked at the Boulton Paul works in Wolverhampton, was treated to the surprise trip at Halfpenny Green Airport.
His family also arranged for him to climb into the cabin of a replica of a Second World War Focke-Wulf fighter plane.
Son Edward, who was behind the surprise, said his aviation had been in his father's blood from a very young age.
Alan's father, Arthur, was a fighter pilot in the First World War, and survived unscathed despite being shot down six times.
In the Second World War, Arthur returned to the RAF to help new pilots, serving in the Military Police during the later years of the war.
As a young man, Alan dreamed of becoming a test pilot, but a motorbike crash put paid to those hopes.
After recovering from those injuries, he went to work for Boulton Paul in Pendeford, working on Rolls-Royce aero engines.
In the 1960s he took his private pilot's licence to fly light aircraft at Halfpenny Green airport in Bobbington.
Alan, who now lives in Claverley, also enjoyed a long and successful career in motorsport, beginning at Silverstone in 1954 by racing an ERA R1B.
He said it had been a birthday to remember.
"It was very pleasant, we flew over to Bridgnorth, where we went over a farmer's field," he says.
"I haven't been in a plane for about 15 years, so it was very enjoyable."
Edward, 52, who said his father had been making large model aircraft since he was eight years old, also brought along a large scale model of a Spitfire and some vintage cars to help him enjoy his birthday.
Edward, who lives in Priorslee, Telford, said his son Oliver, 14, was following in the family tradition by racing cars and learning how to fly aircraft.