This article focuses on the anatomy, literature, and our own experiences in an effort to assist in the decision-making process of choosing between an umbilical or vaginal port. Umbilical access is more familiar to general surgeons; it is thicker than the transvaginal entry, and has more nerve endings and sensory innervations. This combination increases tissue damage and pain in the umbilical port site. The vaginal route requires prophylactic antibiotics, a Foley catheter, and a period of postoperative sexual abstinence. Removal of large specimens is a challenge in traditional laparoscopy. Recently, there has been increased interest in going beyond traditional laparoscopy by using the navel in single-incision and port-reduction techniques. The benefits for removal of surgical specimens by colpotomy are not new. There is increasing interest in techniques that use vaginotomy in multifunctional ways, as described under the names of culdolaparoscopy, minilaparoscopy-assisted natural orifice surgery, and natural orifice transluminal endoscopic surgery. Both the navel and the transvaginal accesses are safe and convenient to use in the hands of experienced laparoscopic surgeons. The umbilical site has been successfully used in laparoscopy as an entry and extraction port. Vaginal entry and extraction is associated with a lower risk of incisional hernias, less postoperative pain, and excellent cosmetic results.