Fly into Rome or Milan?
#2
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This might depend somewhat on where you can get the better deal if you are at all price sensitive. But, all else being equal, I'd fly into Rome. The region between Milan and Tuscany/Umbria is more mountainous and slower driving. Also, if you opt to rent the car at the Rome airport, there are many lovely towns to see as you head north to Siena (assume you don't care to see Rome or Milan, per se, but if that is a consideration, Rome is definitely the better city to visit)<BR><BR>Train vs car depends on whether you do wish to see some of the towns along the way between FCO and Siena and how many in your party and your price sensitivity (car being more economical generally when there are 3 - 4 in your party)..<BR><BR>Again, I'd vote for car for the flexibility of seeing places enroute. There is a premium for picking up at the airport, but there can be a certain economy to having the car an extra couple days, again depending upon the length of your trip. For example, 3 days rental will probably cost you as much as 2 and a 4 day rental will probably cost as much as 1 week, so these considerations might offset the airport surcharge.
#4
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-<BR>If you've ruled out either the Florence or Pisa airports (neither have direct flights from US, have to route thru London or Paris or other European city), THEN I'd pick Rome. You could pick up your rent car at airport. Or proceed directly to Florence (take train from Rome, travel time = 1 hr 35 min) and start your travel in Florence. I'd stay at least 1 nite, pick up rent car & head out.
#6
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We are doing a Tuscany/Umbria tour and opted to fly into Rome. We're taking the train to Florence as we didn't want to have the rental car for our stay in Florence (tough town to drive in and a car is more of a hassle there). We then leave Florence to tour Cortona/San Gimignano, Siena and other hilltowns, dropping the car off at the airport in Rome on our way out.