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Road trip from Milano to siena is 366 km (230 Miles) you can do it in 3 or 4 hours by car. And it's a long trip by bus.
The train takes 4.30' , you have to change train in Florence and it costs about 38 €.
martox45
By car is abt.370 kms. I don't know by train.
Either for bus and train you've no direct connections.
You must go from Milan to Florence and then change in Florence to take a bus or a train to Siena.
We Italian we are not using bus for such a trip.
Train is the best option and also cost (in spite of the recent increases) is not that high (standard fare is abt. € 56 in first class and € 39 in second class).
By assuming you're convinced to take a train here's the link to Trenitalia (in English) with any kind of info you should need for.
http://www.trenitalia.com/en/index.html
I'm also adding an example page with time table etc.
http://orario.trenitalia.com/b2c/TimeTable?stazin=milan&stazout=siena&datag=20&datam=03&dataa=2007&timsh=11&timsm=20&invia=SEND&lang=en&nreq=5&channel=tcom
bellabacioo
If you take the train from Milan to Florence it is about 3 hours on the fast train. By bus from Florence to Siena it is about and hour to an hour and half depending on traffic. Siena is Beautiful that is for sure but make sure you bring your walking shoes. Because there are lot and lot of hills to walk up and down on. If you go let me know i will tell you a great little bar to get a good coffee.