Following a review on the machinability of CFRP composites and multilayer stacks typically comprising metallic and composite material elements, the paper details experimental results when drilling 30 mm thick titanium/CFRP/aluminium workpiece stacks. Testing utilised a modified fractional factorial design based on an L18 Taguchi orthogonal array. This comprised four factors, three of which were at three levels and one at two levels and involved tool coating, cutting speed, feed rate and machining environment. Tools evaluated involved hardmetal and diamond coated carbide in addition to uncoated tungsten carbide drills. Response variables were principally tool wear and cutting force/torque with an end of test criteria of 300m flank wear. Peeling of the CVD diamond coating occurred within the first several holes drilled however this was not a limiting factor in terms of tool life. Principal damage occurred when drilling through the titanium (Ti-6Al-4V) rather than the aluminium (Al 7050) or CFRP (unidirectional “UD” laminates) sections. Best tool life/performance (310 drilled holes) was obtained with the more conventional uncoated carbide drills at lower cutting speed and feed rate. Typically thrust forces increased from 300 N for the first hole to ~2200 N for last hole drilled while torque values were generally below 600 N.cm for worn tools.