The Welshman has been strongly linked with a move to Carlo Ancelotti's side through the close-season, who want the 23-year-old to bolster their options in order to try and regain the Spanish title.
Tottenham manager Andre Villas-Boas and chairman Daniel Levy have thus far maintained that they will not sell their prized asset, who scored 26 goals in all competitions for the club last season.
And Pleat feels the winger would benefit from spending another season in the Premier League.
"I think he's a little bit young to go abroad and I doubt he'd find it easy," Pleat told BBC Sport.
"Many have failed when they have moved overseas. One or two have succeeded, but not many. Most have had a difficult time.
"I think he is young to go, but he might feel that with his partner and baby, it will be a new start for him. It might be better if he stayed, continued to work and maybe next summer leave if that is his wish."
Pleat also backed Levy's stance on Bale's future and believes only a huge offer will tempt him to consider selling.
"Regardless of whether the player wants to leave, the club are in the driving seat and Tottenham have always been very firm on this," the 68-year-old continued.
"If (a club) have strong and brave leadership, which they have at Tottenham, they have to resist any formal offer that comes in, which Tottenham are determined to do.
"If something shattering like £100million is put on the table, then I think even the resistance of Daniel Levy may have to give in, but I think even supporters would understand it for that money."
