Born in Fiorentino, San Marino, Vitaioli has represented three clubs on a permanent basis: San Marino Calcio, F.C. Fiorentino and Sammaurese, and has played for four clubs on loan: Empoli (although he failed to make a single league appearance in the second half of 2005–06 Serie A), ASD Cagliese, Real Montecchio and P.D. Castellarano.