Sastre was one of a great many riders to crash in the road race stages in the Netherlands which began the Giro. He was caught up in a big crash near the finish line of stage 2, though he did not himself fall from his bike, and lost 34 seconds to other contenders like Cadel Evans and Ivan Basso. Sastre fell in stage 3 and was 46 seconds back of the stage winner, and more importantly, fellow contenders Basso and Alexander Vinokourov. Before the transfer to Italy, Sastre was in 43rd place in the overall standings, 1'40 behind race leader Vinokourov. The squad rode solidly in the stage 4 team time trial, coming home with six riders in a time that was good for fifth on the day. Sastre's troubles continued in stage 7 in Tuscany. The route for the stage incorporated unpaved roads, and the day on which the stage was run happened to have heavy rainfall. This made the course muddy and very difficult. Sastre crashed multiple times, and crossed the finish line covered in mud over five minutes behind the other overall contenders. He was speculated to be completely out of overall contention at this point, sitting over seven minutes back of Vinokourov in the standings. Tondó, riding his first Giro, had been near the leaders in stage 7, but had dropped back to help Sastre to the finish. In stage 8, Sastre continued to struggle, and specifically released Tondó to ride his own race. Tondó rode most of the final climb to Monte Terminillo ahead of the pink jersey peloton and took third on the stage, while Sastre lost over a minute to the race's elite and fell to 8'10 back.