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Trenitalia (www.trenitalia.it) have trains from Roma Termini to Chiusi and then to Siena and from Roma Termini to Grosseto and then Siena. The quickest is an InterCity to Chiusi and then a Regional to Siena. The InterCity is 1st and 2nd class while the Regional is only 2nd class. The biggest hassle with trains is that the Siena station is a little out of town and awkward for anyone with luggage trying to reach the town centre. There are buses, but they are not traveller friendly.
You could also take a coach. Which I think is the best bet. The local company is called Sena (part of the Lazzi Group, which I know well), see their website: http://www.sena.it/index_e.htm
or go direct to...
Rome-Siena-Poggibonsi Bus Timetable
These buses leave Roma Tiburtina railway station. So you need to get there first. If you have difficulty understanding the timetable let me know.
As for Siena to Venice, again you could try either train or bus. Regional trains will take you to Florence (Firenze Santa Maria Novella station) and then EuroStar trains to Venice (Venezia Santa Lucia station). Regional trains are 2nd class, EuroStar 1st and 2nd class.
For buses check the Sena website. They have a service running from Sicily to Venice passing through Siena. Have no idea how quick or good this service is. I would probably go for the train instead of the bus on this route, since the hotel could organise transport for you to the Siena railway station.
******
Cheers
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