Renting a car and driving in Tuscanny?
 

6 of us have traveled to Italy a couple of years ago, on a cruise, so we had limited time in different cities / towns. This year we are traveling to Italy in the fall, spending a few nights in 5 different towns / cities. On our itinerary, starting in Rome, is 3 nights in Siena. From there we're heading to Lucca. Our thought was to rent a car the day before we leave, and do a little wine country touring on our own, keep it overnight, and then drop it off in Lucca the next day. The initial thought was to rent a van, but we're questioning whether or not we'll all fit with our luggage; and easily park a larger vehicle So the second thought is to rent a couple of cars, and caravan it around (3 people in each car).
Any thoughts?

Don't rent a van as it will be impossible in village roads.
When there are four of us, we rent one car. Then we rent more cars to take care of a larger group.
You say rent a car " when leaving" which I assume is Rome. There is lots to see enroute to Siena and in it's surrounding area..

A one-day car rental will cost you the equivalent of a 3-day rental. Not very cost-effective. Don't rent a van if you're planning on visiting small villages. What kind of "wine country touring" are you planning? Where? I don't understand your itinerary. How much time do you have in total and how much time for touring around Tuscany (note spelling)?

I rented a van. And drove in small villages.
Well it wasn't easy.
Not easy at all.

If you're contemplating driving between Siena and Lucca on secondary roads in order to explore smaller towns, wineries, etc., a car rental for a day and a half won't allow for much wandering. The drive alone without stops would take at least 3 hours, and probably 4 hours if you wanted to drive through Chianti. FYI, most wineries require advance reservations.

You can research what size van could hold 6 passengers and 6-10 pieces of luggage, but I know it would be bigger than I would want to drive. BTW, I don't see the roads as being as much of a problem as the parking everywhere. Also, I'd be nervous about leaving luggage visible in a vehicle with such an obvious "tourists aboard" appearance.

FWIW, whether you rent one larger vehicle or two average-size cars, a group of 6 takes more time to do everything. Load, unload, pit stops, photo stops, curiosity stops, etc.

Hi M,

You may also want to check if Italy requires the International Driver's Permit and if you have to buy the insurance from the rental company.

((I))

Yes, the IDP is mandatory in Italy. And Italy requires theft insurance when renting a car, unlike some other European countries.

Also, in general, wineries in Italy are not open to drop-ins. As Jean says above, you need to make an appointment. But having a car for exploring the countryside and hilltowns of Tuscany is ideal. You could keep it for Lucca; there's a number of villas open to visit in the vicinity.

The problem is parking. Try to get parking with your hotel.