Italy needed 30 minutes to score the opener but didn’t stop until they had bagged seven behind San Marino goalkeeper Elia Benedettini.
Roberto Mancini’s men started the preparations for the European Champions with a friendly against San Marino in Cagliari, an important game before he has to pick 26 players for the competition.
The Italy CT is still in doubt and has until Monday to decide who will be in the squad for Euro 2020 this summer, and San Marino did well to keep out the Azzurri in the first half of the friendly on Friday.
But captain Federico Bernardeschi eventually scored the opener after 31 minutes, when his shot pierced through Benedettini in the San Marino goal.
The goalkeeper was again troubled when Gian Marco Ferrari scored the second minutes later.
The midfield trident starting the match didn’t convince in the first half and Mancini decided to bring Moise Kean off after only 45 minutes.
The Everton loanee, who has spent the last season with Paris Saint-Germain, was replaced by Matteo Politano, who didn’t need much time to make it three for the Azzurri.
The Napoli forward scored within four minutes of the second half and started the dominance after the break.
Andrea Belotti entered for Vincenzo Grifo and only needed four minutes to score his first goal of the night, before Pessina netted his first goal for Italy after 75 minutes.
Politano secured a brace after 77 minutes, before Pessina added his second of the night in the 86th minute.
Italy were close to claiming the same result as they did against San Marino in 2017, when it finished 8-0, but the referee decided to not add any minutes and blew the whistle after 90 minutes.
Italy (4-3-3): Cragno (Meret 63); Toloi, Mancini (Di Lorenzo 63), Ferrari, Biraghi; Castrovilli, Cristante, Pessina (Barella 88; Bernardeschi, Kean (Politano 46), Grifo (Belotti 63)
San Marino (4-3-3): Benedettini E.; Battistini Ma., Fabbri, Rossi, Grandoni (Vitaioli 51); Golinucci E., Mularoni (Golinucci 89); Tomassini (Brolli 51), Hirsch (Lunadei 51), Palazzi; Nanni (Tommasini 88)