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Arterial stiffness encompasses the global structural and functional modifications that induce progressively increased vascular rigidity, whether associated with pathological cardiovascular or metabolic alterations or not. This narrative review highlights the comparative effects of physical exercise practices, current drug treatments, and approaches based on the use of medicinal plants on arterial stiffness, due to metabolic and/or blood pressure disorders. This review would provide up-to-date information for further experimental and clinical studies concerning the prevention/therapy of high glucose levels and vascular remodelling. Indeed, it is known that physical activities can reduce high blood glucose and blood pressure, allowing the prevention of arterial stiffness. Concerning conventional drugs, some are used to treat arterial stiffness, but their effectiveness is generally limited to treating components of the disease. Eighteen medicinal plant species, belonging to fourteen different botanical families, have potential activities against arterial stiffness in preclinical and/or clinical studies. Several plant extracts reduced the parameters implicated in vascular stiffness, such as the Pulse Wave Velocity, the Augmentation Index, and the Cardio-Ankle Vascular Index. Some plant extracts reduced arterial stiffness by primarily lowering glycemia and/or blood pressure in animal models, which has also been confirmed in humans. By reducing arterial stiffness, plant extracts or derived bioactive compounds not only improved vascular relaxation by enhancing Nitric Oxide production and/or antioxidant defences, but also inhibited inflammation-induced aortic remodelling and promoted elastin neo-synthesis. Polyphenols have often been identified as the main effective compounds involved in these beneficial effects. However, only a few studies explained the mechanisms associated.