Laparo-endoscopic single site (LESS) surgery has recently gained broader acceptance as a less-invasive approach to traditional multi-port laparoscopic procedures. LESS hysterectomy represents the gynecologic surgeon's progression toward this goal of performing minimally invasive hysterectomy procedures through increasingly fewer incisions. Although this procedure offers improved cosmesis and potentially decreased post-operative pain, there are also many challenges to adoption of this surgical procedure. LESS hysterectomy is associated with a steep learning curve and the need for the gynecologic surgeon to adopt new technologies and develop a new set of surgical skills. Following the basic principles of LESS surgery is essential for the gynecologic surgeon to safely and efficiently adopt this surgical procedure. Advances in surgical instrumentation will continue to allow surgeons to perform increasingly complex LESS surgical procedures in the future.