The 2008 Giro d'Italia began on 10 May, with Stage 11 occurring on 21 May. The first stage, like it had been in 2007, was a team time trial, a stage where each member of the team raced together against the clock. This stage was won by the American team , who had viewed it as their primary goal in the Giro. It allowed their leader Christian Vande Velde to wear the first pink jersey as race leader. Unlike in most cycling Grand Tours, the first road race stage 2008 Giro was not a flat stage decided by sprinters, but rather one over a hilly course that would be won by a breakaway or a strong climber. Though Stages 3 and 4 were both flat and conquered by sprinters, this meant that it was unlikely that a sprinter would get to wear the pink jersey at any point in the race.
The first half of the 2008 Giro contained six stages classified as medium-mountain, though many of them contained difficult, selective climbs that broke up the racing peloton. The sixth stage was shortened from its planned length of . This was due to riders speaking with race officials and asking that the finishing circuit be eliminated, as the long transfers between stage finish towns and start towns the next day had afforded them little rest to prepare for such a long stage. In that same stage, a 12-rider breakaway finished sufficiently ahead of the peloton that one of its members, Giovanni Visconti, became the new overall race leader, a lead that he would maintain for more than a week.
s.t. indicates that the rider crossed the finish line in the same group as the one receiving the time above him, and was therefore credited with the same finishing time.
Stage 1
10 May 2008 — Palermo, (team time trial)
The Giro began, like it had the previous year, with a team time trial (TTT) on one of Italy's islands, this year in Sicily. The course was flat. There was speculation that this stage would result in a second American cyclist to wear the pink jersey (the first having been Andrew Hampsten in 1988), as , , and were all considered favorites to win the stage and all had strong American time trialists on their squads. , one of the first Professional Continental teams announced for the race, held a special training camp in Spain a week before the race specifically to work on their TTT skills.
The early time to beat was set by the second team to take the course, , clocking in at 27' 05". After three other teams came , who finished with only the minimum of five riders together (the team's time is taken for the fifth rider to cross the finish line, with any riders who are dropped given their own times) after David Millar was dropped in the final kilometer. Christian Vande Velde was the first to cross the line for , after 26' 32". That Vande Velde had been the first over the line rather than time trial specialist David Zabriskie had not been specifically the plan. The next team on course was , who were nine seconds slower than at the first time check and finished in 27' 01". and were both ahead of at the first intermediate time check, but faded toward the finish and clocked in second and fifth, respectively. 's time held up to the end of the stage, affording Vande Velde the first pink jersey.
Stage 2
11 May 2008 — Cefalù to Agrigento,
This was a hilly course, in contrast to most Grand Tours, which begin with flat road stages. It contained two categorized climbs, and favored an attacking rider.
The significant breakaway of the day comprised David Loosli and Jérémy Roy, after Dionisio Galparsoro had been brought back into the peloton after an earlier attack. Loosli and Roy attained a maximum advantage of over ten minutes. With remaining in the stage for the peloton, a significant crash occurred as they went over a railroad crossing. David Zabriskie was the most seriously hurt, needing to be taken away from the race in an ambulance.
Loosli and Roy were caught with left to race, as the finishing circuit in Agrigento began. had been at the head of the peloton, protecting race leader Christian Vande Velde, for as long as they could, and during the circuit took over the pace-making. The hilly and difficult circuit made it so many riders lost contact with the leading group, until only a small number of climbers and overall favorites were with the leaders. Joaquim Rodríguez was the first of this group to attack for the stage win, but he was caught in the final few hundred meters by a quintet of Italians, Riccardo Riccò, Danilo Di Luca, Davide Rebellin, Franco Pellizotti, and Paolo Savoldelli. Riccò was the first across the line for the stage win, while Pellizotti's ten second time gap over Vande Velde in 19th gave him the pink jersey.
Stage 3
12 May 2008 — Catania to Milazzo,
