This episode was The Amazing Race’s 300th episode.
Upon arrival in Palermo, teams had to head to the Teatro di Verdura for their first clue. However, they found a series of tambourines marked with a time the following morning, telling them to instead spend the night dancing the tarantella with a band of musicians.
The leg’s Roadblock where one team member drove a go-kart along the old route of the Targa Florio auto race around Mount Pellegrino. If they could complete the course within 4 minutes and 7 seconds, they would receive their next clue from racing legend Nino Vaccarella. If not, they would have to follow the pace car back to the starting line and try again, around a 20-minute wait. Once the racers got their next clue, they would be driven back down the mountain by a retired race car driver to join their teammate at the Antico Stabilimento Balneare.
The Detour was a choice of Painters and Posers. In Painters, teams traveled to the Tonnara Florio where they had to restore a fresco while lying on their backs on a high scaffolding, as Michelangelo (according to legend) did when painting the ceiling of the Sistine Chapel. Once the artist was pleased with their work, she would give them their next clue. Teams were warned that there were only 4 available spots at the Painters Detour, leaving the others to wait or switch tasks. In Posers, teams headed to the Teatro Politeama Garibaldi and watched a series of opera performers. They then had to head back stage and match the performers to their costumes, characters, and plays in the order the performers sang by writing down the answers in a playbook. Once the costumista judged their playbook correct, teams would receive their next clue.
Tim and Te Jay arrived last at the Pit Stop but it was a non-elimination leg so they were not eliminated.