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stay in siena or montalcino

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trying to decide where we should stay, siena or montalcino, will be travelling from the C.T. on Thursday 18th October ( by train most likely, could look at a car & driver from Florence if needed) and will have until 23rd October when we will fly back to Australia from Rome. We do not want to drive ourselves so will be looking to book daytrips & private tours as we want to visit and spend quite an amount of time at Sant'Antimo - (even considering hiking there from Montalcino on one day) and Monte Oliveto Maggiore, plus touring the small villages and towns in the surrounding area, we would like to visit a small olive grove where traditional pressing methods are used plus some wineries, my question is - do I look for accomodation in montalcino or siena, this is our 1st visit to Italy, your thoughts and assistance will be greatly appreciated, we do not want to drive as we think it will be a bit too stressfull

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