Pathologies comprising more than half the length of the trachea are a challenge to the reconstructive surgeon. Innovative tracheal transplantation techniques aim to offer the patient a curative solution with a sustained improvement in quality of life. This review summarizes the authors’ experience with the rabbit as a versatile model for research regarding tracheal transplantation. Because of the segmental blood supply of the trachea, it is not feasible to transplant the organ together with a well-defined vascular pedicle. As such, the key element of successful tracheal transplantation is the creation of a new blood supply. This vascularized construct is created by prelaminating the rabbit trachea heterotopically, within the lateral thoracic fascia. After prelamination, the construct and its vascular pedicle are transferred to the orthotopic position in the neck. This model has become gold standard because of the advantages of working with rabbits, the anatomy of the rabbit trachea, and the reliability of the lateral thoracic artery flap. In this paper, the key elements of surgery in the rabbit are discussed, as well as the tracheal anastomosis and the harvest of the lateral thoracic artery flap. Practical tips and tricks are presented. The data described in this review represent the fundaments of ongoing translational research in the center over the past twenty years.