In her new role, TTG 30 Under 30 alumnus Ayling will look after agents in the home counties, reporting into head of sales Rebecca Bryson.
She will work alongside fellow trade sales manager Isabel Amison to grow Caribtours' profile among agents across the UK.
Ayling, a member of the TTG 30 Under 30 class of 2015, joined Classic in 2010 as a sales executive and for more than a decade represented the brand as a regional sales manager.
"Sarah will help to grow new business through luxury travel agents and advisors," said Caribtours chief executive Paul Cleary.
He added: "This appointment further underlines our commitment to developing and strengthening relationships with our trade partners."
Ayling brings more than 20 years' travel industry experience to her new role with Caribtours, including "extensive knowledge of the Caribtours portfolio" and "excellent" existing relationships with the trade.