Product and purchasing manager Mirko Buzzelli joins from easyJet holidays and will oversee Classic’s product in Italy and Croatia.
Barcelona-born Alex Callahan, meanwhile, joins from Yourtravel and will take up a like role with responsibility for mainland Spain, the Balearics and Gibraltar, a brand new role at Classic.
Both Buzzelli and Callahan will oversee dedicated teams of product and purchasing executives.
Alex Gavalda, Classic’s director of product and commercial, said: "Both Mirko and Alex bring a wealth of experience and expertise to Classic.
"As true destination experts, they’ll source new quality product to add to our existing programme and support our sales team with the breadth of knowledge that they bring to both roles."
Gavalda added: "Their appointments underscore our commitment to destinations where we are already very well established and demonstrate our investment in the continued development and future success of these key short-haul destinations.
"Alex’s position, heading up the Balearics and mainland Spain, is a brand new role which reflects the growth that we plan in those destinations."
Callahan said his aim would be to expand Classic’s range of hotels, experiences multi-centres and tours, adding he was excited to join a business "in full transition".
Buzzelli added he would be seeking to refresh Classic’s accommodation options and itineraries in Italy.