In our institutes, microvascular surgery has been effectively used in reconstructive digestive tract surgery, including esophageal reconstruction and hepatic arterial reconstruction. Free jejunal transfer combined with a gastric pedicle or microvascularly augmented elongated gastric pedicle has been utilized for total esophageal reconstruction. A microvascularly augmented jejunal pedicle or colonic pedicle has been applied in thoracic esophageal reconstructive cases with gastrectomy. Moreover, microvascular surgery has been performed in the reconstruction of the hepatic arterial system in the surgical treatment of pancreatic or bile duct cancer and living related-donor liver transplantation. Some pitfalls in selection of the recipient vessels and handling the intraperitoneal vessels for microvascular anastomosis are also described. Although microvascular surgery has been carried out by plastic and reconstructive surgeons in a team surgical approach, revisions in the medical educational system to create a new-type of surgeon with practical skills and clinical experience in both digestive tract and microvascular surgery will be required in future.