You can use bahn.com to check schedules. It looks ast though you can get a regional train from Siena to Florence and then go by Eurostar Italia train from Florence to Milan. This second portion is worth booking in advance - booking for end August will open end May - 3 months ahead. Journey time 4.5-5hrs so you'd still need to leave fairly early to get to the airport in time. There are also routes with more than a single change taking more like 6-6.5 hrs

It is almost certainly too early to book as yet as the new timetables are not available.

Looking at the same journey in April for comparison, it is going to take you around five to five and a half hours.

Currently, there is a train from Siena at 8:47 going direct to Florence, then a 55 minute wait for the 11:00 fast train to Milan central, then another 45 minutes on to the airport. This will get you there around 1:40 but has the advantage that it is only two changes of train.

If you missed the 8:47, there is another train from Siena at 9:18 which arrives at Florence at 10:50, but this would only give you 10 minutes to change trains for Milan, or wait for the 12 o'clock train.

Anything later from Siena under current timetables will almost certainly see you arriving at the airport too late.

Are you willing to take the bus from Siena to Florence and then transfer to rail? Might be a bit faster for you. Are you willing to stay in Florence the last night instead of in Siena? In Milan instead of in Siena?

Today, it might make better sense to get an Italotreno high-speed train from Florence to Milan Porta Garibaldi, from where there's a train into Malpensa every half hour. Most of these Malpensa trains start at Milan Centrale, where they connect with Trenitalia

It's possible this isn't fully covered in the Bahn site, and in summer there are usually a few trains a day from Florence into Malpensa. These may not yet be on the Italian website either.

But for peace of mind: You need the Trenitalia website for trains from Sienna to Florence, and for their trains to Milan, the Italotreno site for trains into Porta Garibaldi and the Trenord site (marketed as http://www.malpensaexpress.it) for trains from central Milan into Malpensa.

I don't know whether Italy's railways will sell through tickets via competing railways, but it's almost certain that for the best deals on the main Florence-Milan chunk you need to buy from the operating company's website

You could take the Sena bus that leaves Piazza Gramcsi at 7:20 and arrives Milan at 11:50. It drops you at Milan Rogoredo station which is on the metro. You would have to take the metro to Milan Centrale and catch a train or bus on to the airport.

www.sena.it

I would stay closer to or in Milan.

Thanks thanks, Loco2com, Willit, Dukey and flannerukthats more solutions than i have unearthed in one month. I love the bus to florence and train to malpensa ideas. And living in a country with nationalised railway never struck me that there could be competing systems on public transport!! Cant spend the night in florence as we are keen on a clear day in Siena.

May i be greedy and ask if there is a sensible overnight way to get to Prague from Siena with a kid and big bags? My husband will also be there, so two sets of hands on board but not exactly backpacking freedom. Then, i can ditch the flight entirely and we can snooze our way out of Italy.

Thanks kybourbon. One more option for us although not sure about hauling bags and a kid on a metro ride. Italy from past experience, can be inconsistent on elevators and escalators.