Vilcinskas made his official debut as an amateur rider at the 1996 Summer Olympics in Atlanta, where he competed along with his fellow cyclists Linas Balčiūnas, Raimondas Rumšas, Remigijus Lupeikis, and Ivanas Romanovas in the men's road race, but did not finish the course. During his amateur career, Vilcinskas had awarded a silver medal in the same discipline at the 1997 Lithuanian championships, but turned himself into pro in 1999 with Belgium's Palmans-Legal cycling team, and thereby picked up his first career title at the Memorial Philippe Van Coningsloo.