Orlandi spent his career playing for several amateur teams, including Akragas throughout the 1970s and the 1980s, and being nicknamed l'agricoltore (the peasant) because of his particular running style.

[3] After a short experience working as youth team coach for Vicenza, Orlandi joined Reggina in 1989, becoming their Allievi Nazionali (16-year-old youngsters) head coach, being then promoted at the helm of the Primavera (main youth team roster) soon later,[4] and successively serving as assistant manager to Franco Colomba during the amaranto's 2000–2001 campaign.

[6] During his stint as first team coach, results dramatically improved and Reggina managed to mathematically save themselves from relegation in advance of one week.

In his second season as Reggina coach, the team struggled to achieve positive results, and this ultimately led to Orlandi being dismissed from his post on December 16, two days after a home 0–2 loss to Sampdoria, leaving the team in second-last place with 12 points achieved in 16 games.

He then served as Grosseto head coach in the Serie D league from February to June 2016, before taking over at Chieti that same year in July.