I want to fly into Florence stay 2 nights and ultimately spend most of my time in Montepulciano before heading for 2 nights in Venice. Is it best to drive from Florence to Montepulciano and then to Venice or to take the train or combination of both? If rent a car, is it best to hire a driver?
Given the total uselessness of a car in Venice (for very obvious reasons) and the cost and difficulties of parking in both Venice and Florence (explanation below), train seems by far the easiest and most sensible option.
Hiring a car plus driver will be very expensive indeed. You can do it if you like ...all depends on your budget...but it is certainly not necessary,
Florence (like most Italian cities, towns and many villages too) has a restricted traffic zone...a ZTL...monitored by CCTV cameras and with automatic fines taken from your card, plus admin fees. Hotels can, in theory, provide you with a pass which allows you to take your car into the ZTL for unloading and loading purposes...but they do not have to do so. And why go through all that hassle?
Italian trains are safe and comfortable. The network is extensive and services on most routes frequent. It is possible to get excellent advance online discount fares for the high-speed train routes (though online tickets tie you to specific departure date and time).
Look at the official Italian railway website in English for train times, details, fares and online booking:
Use the Italian names: Firenze S. M. Novella for Florence's main station, Venezia S Lucia for Venice's.
Florence>Venice on the high-speed trains takes from just 2h 5m.
The newer Italo high-speed trains also run this route. Journey time and fres are much the same as Trenitalia. Italo too has online booking with discount advance fares. English site:
Florence>Montepulciano is not a high-speed route. Journey time is from just over 2.5 hours, with at least one change of train (this is very easy to do).
Venice to Montepulciano takes much longer.
I'd suggest that you use the train to get from Florence to Montepulciano, hire a car there if you really, really want to (though there are local buses as well of trains, of course) and then take the 0937 departure from Montepulciano to Venice, taking 4h 24m.
Good advice above. You don't say how long you are staying in Montepulciano but you might enjoy a rental car there. It's a small town and if you'll be there a few days, you may want to get out and explore the area because it is just gorgeous. The roads are good and well marked so don't be afraid to drive yourself. Get a rental with a GPS system and you'll be fine. We always have them program in the return address so we can get the car back to them without delays. Most come with it done already but ask to be sure. If you don't speak Italian, have them put it in English too. We usually have a leased car but when we rent, use [original link] and they are reasonable and reliable. If you want an automatic transmission, you must order ahead of time so they will be sure to have one. If you order ahead, it is not a problem.