Tour de France 2009

I'd say pick Astana if you to get this the easiest way. To avoid losing alot of time on the time trials, make sure you choose which riders to ride them with the D-PAD. You should probably avoid riding with your general classification hopes. I'd suggest using Contador, he's the best in the mountains and should get you this achievement without too much of a struggle.

On the mountain stages a way to get a big gap on the rest is to attack before the last mountain, preferably on the second last mountain if it is close to the last one. You will get a nice gap if you put your effort to 100%. They will probably catch up a little on the final climb, but you should make it to the finish line. Just in case your rider somehow cracks. Reload the game without saving and experiment with the effort, this shouldn't happen though unless you attack way too early. I suggest only attacking if the last 2 climbs are within the last 60 kilometers.

Doing this with Contador should also get you the White Jersey achievement.