In cycling, the presence of drag reduction from drafting, when multiple cyclists ride in tandem, is a considerable area of performance enhancement for a cycling team and the customisation of this tandem group has the potential of maximising the drag reduction for the entire group or a specific cyclist. The flow interactions between two tandem bluff bodies is complex and incorporates several fluctuating variations in flow phenomena which have considerable effects on the drag forces experienced. An experimental campaign for tandem finite cylinders and cyclists of differing sizes and in different spacing configurations is undertaken, including a drag force measurement and PIV flow visualisation campaign. It is observed that differing magnitudes of drag reduction occur for tandem cylinders and cyclists, which are however, caused by similar variations in flow structures. The size and spacing ratios are found to have notable impact on drag reduction for tandem objects.