Totally minimally invasive Ivor-Lewis esophagectomy (TMIIL) is associated to lower rate of post-operative complication, decreases length of hospital stay and improves quality of life compared to open approach. Nevertheless, adaptation of TMIIL still proceeds at slow pace, mainly due to the difficulty to perform the intra-thoracic anastomosis and heterogeneity of surgical techniques. We present our experience with TMIIL utilizing a stapled side-to-side anastomosis. We retrospectively evaluated 36 patients who underwent a planned TMIIL from January 2017 to September 2020. Esophagogastric anastomoses were performed using a 3-cm linear-stapled side-to-side technique. General features, operative techniques, pathology data and short-term outcomes were analyzed. The median operative time was 365 min (ranging from 240 to 480 min) with a median blood loss of 100 ml (50–1000 ml). The median overall length of stay was 13 (7–64) days and in-hospital mortality rate was 2.8%. Two patients (5.6%) had an anastomotic leak, without need for operative intervention and another patient developed an anastomotic stricture, resolved with a single endoscopic dilation. Chylothorax occurred in three patients; two of these required a surgical intervention. Pulmonary complications occurred in six patients (16.7%). Based on Comprehensive Complications Index (CCI), median values of complications were 27.9 (ranging from 20.9 to 100). The results of our study suggest that TMIIL with a 3-cm linear-stapled anastomosis seems to be safe and effective, with low rates of post-operative anastomotic leak and stricture.