You would probably need at least 3 cars with hired drivers if your group is 9 (4 people per car). It

I would take the train to Orvieto, pick up a car, visit Orvieto, and then stay in San Quirico for 4 nights. Smallish town - but everything you need for 4 nights. Fantastic countryside. Fourty-five minutes to Siena, 15 mins to Pienza, 25 mins to Montepulciano, 15 mins to Montalcino.
But if Tuscany is the primary goal, you can rent the cars (you'll need two) in Civitavecchia and start heading wherever. I like Orvieto a lot, but getting there by train from the port involves 1-2 connections and takes longer than driving. Also, if you rent the cars at Civitavecchia, you only handle your luggage once as opposed to schlepping luggage on and off trains multiple times. If you'd be arriving in Orvieto on a Saturday car rental in perth western australia afternoon or any time on Sunday, you wouldn't be able to rent the cars as the office would be closed. car rental in perth western australia It's also closed for a few hours for lunch Monday-Friday.
If you definitely don't want to rent the cars at the port, you could also train to Grosseto (an hour or less) and rent the cars there, although I think the same Saturday, Sunday and lunchtime closing hours would apply.
I didn't know whether you were returning car rental in perth western australia to Rome for a day or two there - or just leaving Tuscany and then getting on the flight. That's why I advised Orvieto. It is too early to book flights - so determine what you want to do and then book the time/day for your flight home.
Wow! So glad I stumbled upon this. I'm planning a 15 day trip with my daughter car rental in perth western australia from US to Italy in June. Flying into Milan Malpensa, planned on getting to Florence by train, 2 night stay, then rental car to Tuscany for at least 5 nights, then to Rome. But by car, or return car and take the train. I've been warned about driving in southern Italy. So I'm looking at options such as train passes or car/train combo passes. Want to see Pompeii CLIMB Vesuvius! Then take the train to Venice for the last 2 nights. car rental in perth western australia Final trip back to Milan for a 1pm flight car rental in perth western australia on a Sunday. By car or train? hmmm so much to plan and your expert advice is so greatly appreciated!!!
You should start a new thread car rental in perth western australia for your trip (make Italy, two weeks, your title) because you will get much more advice specific to your needs. This thread will probably only bring answers to dperry's question about transportation and lodging in Tuscany.
First advice for you: the big loop you are thinking about into and out of Milan wastes a lot of travel time and money. Please car rental in perth western australia re-think your itinerary, based on those things you are most excited to see, with a good map in hand.
Look at multi-city tickets (this is not two one way tickets - sometimes people say, open jaw). Fly into Rome or Naples (since you want to go to Pompeii) and out of Venice, or Milan if Milan is a must see city for you.
It's very difficult to time the olive harvest, because it depends partly on the weather in the spring. This year we had a rather late harvest, because car rental in perth western australia the spring was cold and damp. Often the harvest is in late October. However, if you join a for-tourists olive harvest tour, they may harvest it at any time. Once they're ready, the olives can hang on the tree for several more weeks. They lose some of their liquid, but don't spoil.
I don't really see the big deal about picking the olives, but maybe that's because it's no novelty to me; to me it would make more sense to do an oil tasting. There are various varieties of olive, each with different characteristics. We have a tree of the raggia variety, which is supposed to be the best for preserved olives.
regulars on this board are doubtless fed up with my mentioning it, but the ancient city of Orbetello on the southern Tuscan coast would suit you perfectly. It's on a direct train line from Civitavecchia, and is large enough to be interesting, without being overwhelmed by tourists. It's set in a lagoon with plenty of beaches to relax on, and lots of countryside and coast to see, loads of good restaurants too.
Orbetello would be fine if the group is willing to experience a different Tuscany from the usual circuit. However, if they want to visit the class Tuscan hill towns, it's a long drive from most of those to Orbetello. For example, it would be at least a 2-hour drive from Orbetello to Montepulciano.
Orbetello is only an hour's drive from Sovana, car rental in perth western australia a very pretty Tuscan town. It's also right next to the Maremma natural park, and you can get boats to the Isola del Giglio from nearby Porto Santo Stefano. car rental in perth western australia There are also many interesting places to visit in nearby northern Lazio, a beautiful area almost totally overlooked by tourists. Tuscania is an interesting and charming hill town, less than an hour away. Tarquinia is not only a lovely town, but it also has one of Italy's best Etruscan museums, and a very important Etruscan necropolis, with beautiful painted tombs.
Considering the size of the group, I would suggest renting two cars. It might be cheaper than renting a van for a group of this size, and it would also allow splitting up some days to pursue different interests.
Anyone planning to drive must get an IDP (International Driver's Permit) to drive in Italy. You can get these easily and inexpensively at an Automobile Club. The IDP has to be carried ALONG WITH your normal license.
car rental in perth western australia The group has been to Rome several times, most recently last year so we are not interested in spending time there this visit. (But may do a day trip to Florence as I love this city, and find it achingly car rental in perth western australia beautiful)
if you can get there, Siena could be a good centre - plenty to do in the city itself, loads of nice restaurants, good communications by train and bus. also you might like to think about using a car/guide car rental in perth western australia like Hills and Roads :
I've not used them myself, but they get consistently good reviews car rental in perth western australia here and on TA. They are quoting 365 for transfers to Siena from Rome for more than 4 people, and could do such day trips as you wished during your trip.
You would probably need at least 3 cars with hired drivers if your group is 9 (4 people per car). It is a 3 hr drive to the Val d'Orcia area in Tuscany, or to Florence. If these guides are to also drive you to other destinations and back to Rome, you would need them for 4 days. I have no idea of how much it would cost - but it sounds like a huge amount of $$$$$.