Background: Inguinal lymphadenectomy remains the gold standard for the treatment of inguinal lymph node metastases from penile carcinoma, melanoma, Merkel cell carcinoma, and squamous cell carcinoma (SCC). This procedure is associated with significant complications. In order to reduce morbidity, minimally invasive approaches have been described. We report our preliminary experience with robot-assisted inguinal lymphadenectomies (RAIL). Methods: RAIL was performed according to the Sotelo technique. When indicated, a robot-assisted pelvic lymphadenectomy (RAPLND) was performed. We recorded age, sex, comorbidities, baseline oncologic diagnosis, operative time, hospital stay, lymph node yield, complications, time to drain removal, and oncologic outcomes. Results: From December 2016 to February 2019, 13 patients underwent RAIL. Median age was 65 years (range: 31–85 years). Primary malignancy was melanoma in five patients, Merkel cell carcinoma in four, dermal duct tumor in one, penile cancer in two, and SCC in one. RAIL was monolateral in 12 cases and bilateral in 1 case. A total of 10 monolateral RAPLNDs were performed; median operative time was 279 min (range: 169–320). Median lymph nodes yield was 11 (range: 2–24) for monolateral RAIL and 9 for monolateral RAPLND (range 2–24). Median hospital stay was 4 days (range: 2–5). No procedure was converted to open. Median follow up was 16 months (range: 5–31). Five Clavien-Dindo grade I complications were recorded. Median time to drain removal was 32.5 days (range 7–65). Three recurrences and two cancer-related deaths were recorded. Conclusions: RAIL is feasible and associated with a short hospital stay, with little incidence of perioperative complications.