After leaving secondary school, Bennett worked as a freelance archaeologist in England and Germany, before entering the University of Durham as a mature student where he graduated with a BA (Hons) in Archaeology in 1978.
The title of his PhD thesis was The Setting, Development and Function of the Hadrianic Frontier in Britain.
From 1985 to 1995, Bennett worked for a New York travel company, guiding for institutions such as the Smithsonian and the Metropolitan Museum of Art, and working as Tour Leader and Archaeological Guide Lecturer on boat cruises around Europe and Scandinavia, the Mediterranean World, and South America.
Bennett's fieldwork experience extended from rural and urban salvage excavations in Britain, Romania, and Germany to a later research project, studying the architecture of the Moldavian and Ottoman castle of Belgorod-Akkerman, in Ukraine.
He was elected a Fellow of the Society of Antiquaries of London in 2002, becoming only the third person in Turkey to receive that distinction.