Free-floating thrombus (FFT) of the cervicocranial arteries is a rare neurovascular condition. Up to now, there is no standardized definition for FFT. Therefore, FFT is occasionally mistaken for intraluminal thrombus (ILT) or smooth mural thrombus. The most precise and ideal definition of FFT would be a long-extended intraarterial thrombus that is attached to the arterial wall with its one end, while its other end is surrounded by blood flow and moves freely with the cardiac cycle. FFT usually manifests as an ischemic stroke, thus it is considered as an emergency case. Herein, we report a rare case of symptomatic FFT in the left vertebral artery extending from V0 to V2 segments in a middle-aged smoker, who presented with multiple embolic strokes in different territories of posterior circulation and was successfully treated medically. This case sheds light on the challenges of the clinical approach of FFT in the vertebral artery and it is an attempt to draw attention to the necessity of conducting a large-scale study to find out the ideal approach to manage such conditions.