Vertebral artery dissection (VAD) is a rare cause of ischemic stroke in young patients. The largely nonspecific symptoms and delayed presentation pose a serious diagnostic challenge. Medical management with either anticoagulation or antiplatelet therapy is recommended, but there are no reports of successful dual therapy. We report a case of spontaneous bilateral vertebral artery dissections (VADs) treated with both anticoagulation and antiplatelet therapy and a literature review on clinical presentation and the current medical and surgical management options. A 37-year-old healthy female presented to the emergency department with worsening neck pain and headache for two weeks despite over-the-counter medication, block therapy, yoga, and deep tissue neck massage. She denied any trauma but admitted to multiple roller coaster rides over the past few months. CT angiography was concerning for VADs, and MRI brain revealed multiple strokes in the left posterior inferior cerebellar artery (PICA) territory. Cerebral arteriography confirmed the diagnosis of VADs. The patient was initiated on warfarin, along with atorvastatin and aspirin. She was discharged home with no complications and followed up with neurology as an outpatient. MR angiography after three months revealed complete resolution of the dissection. The patient did not report any bleeding complications from dual therapy.