The permanent maxillary canine is the second most frequently impacted or displaced tooth. The standard treatment for an impacted canine includes, among other things, surgical exposure and orthodontic alignment. Surgical techniques for this procedure vary depending on whether the tooth is labially or palatally impacted, while orthodontic techniques vary according to clinical judgment and experience. Autotransplantation is a treatment alternative for impacted canines with complete root formation. The success of tooth transplantation depends on the vitality of the periodontal ligament (PDL) attached to the donor tooth, and its viability decreases when it is exposed extraorally. This article reports on maxillary canine autotransplantations combined with connective tissue grafts (CTGs) and orthodontics. The recipient mesiodistal space was created orthodontically and the recipient socket was prepared using dental implant drills. Following transplantation, bone defects were grafted using guided bone regeneration (GBR). At 4 years post-transplantation, the soft tissue level was stable and periapical radiographs showed a practically normal contour of the alveolar crest around teeth 13 and 23. The two permanent canines presented no root resorption and ankylosis, and no signs of inflammation or bleeding were observed. The procedure used in this case report demonstrates that canine transplantation combined with GBR, plastic surgery procedures, and orthodontic treatment may yield acceptable and predictable esthetic results.