Windsurfing now has more than 50 years of history, and continuously for ten editions, it has been included in the Olympic program as a sailing class. The introduction of hydrofoil technology allows for reaching very high speeds, adding spectacularity and attracting the media’s interest. The most popular disciplines are wave, freestyle, slalom, and course racing, but most enthusiasts are free riders who appreciate this sport’s speed, contact with nature, and relative safety. The injury rates range between 0.22 and 5.2/1000 h of windsurfing. Most of the reported injuries are acute (69–78%) and mainly affect the lower limbs (38–59%) and the head/neck region (16–26%), followed by the trunk (8–19%) and upper limbs (6–20%). Most acute injuries are caused by collision with equipment (65–75%), while the most frequent dynamics are uncontrolled falls (37%) resulting in “foot strap injuries” and “catapulting.” Lisfranc injuries, concussions, anterior shoulder dislocation, and wounds represent the most typical windsurfing injuries. Overuse injuries have an incidence of 0.08/year and 0.092/1000 h of windsurfing; most are low back pain, epicondylitis, and exertional compressive neuropathies. In therapeutic choices between conservative and surgical treatment, the expectations of windsurfers, the specific discipline they engage in, and any possible career repercussions must be carefully considered. Educating athletes on the appropriate technical execution and rig choice is integral to rehabilitation. Windsurfing is physically demanding, and adequate endurance and strength training is advisable to prevent acute and overuse injuries.