Help with Tuscany/Palio desicion

One husband + one wife + 3 daughters= 5 people.
These 5 people are going from Venice to an unspecified location outside Siena. Their plan, as I understand it, is to take a fast train to Florence then from Florence a bus or a train to Siena (base price=€50+ p.p.=€250 for 5, unless willing to lock into a pre-purchased discounted ticket). Once reached the Siena rental car office, approximately 4 or 5 hours after their departure from Venice, they intend to rent a car to reach their out of town destination.

If my assumptions are correct, and this were my trip, I wouldn't bother with the train. I would book the rental car with a pick up at Venice (Piazzale Roma, near the station) and drive at my leisure the 3.5 hours to the Siena area. Since you intended to rent that car on that day anyway, you might as well do it from the start the morning you depart from Venice. From Venice to Siena it's practically all freeway driving, a little over 300km (about 200 miles). All you need is about 20 liters of fuel (if a diesel about €35) and the freeway toll from Mestre to Firenze Impruneta exit (about €25). So the 5 of you get to go, at your pace, maybe with some pit stops in between, from Venice to your final destination for about €60, all included, certainly less than what the train would cost, but above all without the hassle for your husband of having to carry the luggage for four women on and off the trains (been there, done that! No thank you!).
If you were going to Florence and did not intend to rent a car, but rather stay in Florence, then the train would make sense. But given the fact you are going to a countryside location where you intend to rent a car that same day anyway, I think I would go with my plan.

Regarding the Palio, it's an experience I would not miss. You don't need to attend all the pre race events, but don't miss the big day and maybe some trials.

Thank you. Well my original thought was to take a train to Siena and rent the car from there - but your option seems much more cost effective. I was just trying to get the driving to a minimum because I hear the driving can be a bit crazy. So - now we are right outside of Siena. My concern now is if we should take a day off from either Venice or Rome to give an extra day in Tuscany because of the Palio. However, if we drive from Venice, we might get some great sites in along the way, which might make up for some of the missed opportunities since Palio would be time consuming. Florence is not on out trip plans - I only threw it out there for a potential place to rent a car. I haven't looked yet - but thought of getting the car and dropping off in Siena because of multi-city drop fees, but maybe that isn't an issue. Will it be close to the same cost of getting a car in Venice and dropping off in Siena? We could take the bus from Siena to Rome - my understanding is that option is cost effective and straight forward. I don't think my husband wants to drive to Rome! Are the day allocations pretty good - 4 Venice - 4 Tuscany and 5 Rome?

Several cities hold palio events (Ferrara comes to mind); these are specific to the city and celebrations do not spill over into the province or region. You may have a slower drive to your place, but not have to deal with carousing in the countryside.

Your allotment of time sounds fine, you can take a sidetrip to Padova from Venice if you need to fill more time.

You are from San Francisco, not from some prairie farm. If you can negotiate the traffic in SF, the traffic in Italian cities won't be much worse, therefore nothing much crazier than what your husband is already used to. The only caveat to be aware of is the limited traffic zones (Zona Traffico Limitato or ZTL) in the historical centers. Those areas have traffic restrictions to motor vehicles (pedestrian and residents only allowed) and are enforced by cameras. Freeways work the same as in California. The only difference in Europe is that the left lane is passing lane only and one cannot cruise in it. Just move the rightmost lane as soon as you have completed passing a vehicle.
In Tuscany you will be driving a lot on curvy country highway. Just take highway 84 from Redwood City to the ocean near Pescadero and that will be your Tuscany driving course.
Since you have a car you should drive it to Rome. There are no extra fees in Italy for dropping the car to a city different from the pick up. The easiest drop off in Rome is at a Tiburtina Station office. The Tiburtina train station is very close to the freeway exit coming from Roma Est (east). As you approach Rome on the A1 freeway follow directions to Napoli (not Roma Nord). Then take the A24 Ovest to Roma Est (look at google maps). It's longer but easy. When the freeway ends, right after a tunnel, you are near Tiburtina station. Just set your GPS with the address.
Another alternative is to drop off in Orvieto and continue by train. Another yet is to drop off at the Fiumicino airport and take a taxi.

Do what Roberto layed out, his info is spot on.
Use Kemwel or Auto Europe for low cost rentals.

Marie,

Do not miss the actual day of the Palio. We were in Tuscany in June/July and planned to go to Siena and the Palio. After reading about the crowds, we were leaning to just go to one of the trial days, but as the day approached we decided to go for it. It was one of my most memorable experiences in all of Europe, The line to get into Il Campo is packed like sardines, but not much worse than major sporting or concert events in the US. Once you get in to the piazza, turn right and to the back, there is a slight rise, so you can see most of the event. A couple of things to remember: no WC's in the Campo so plan accordingly, pickpockets are at the event so again plan accordingly, arrive to the Piazza del Duomo to watch the parades (it started at 3 pm in July). We came so close to missing this, because we didn't want to deal with the crowds. I am so glad that we saw it.

Thanks! I have been reading about the crowds as well, but my understanding is that there is such excitement in the air that we just can't miss it. I'll have to convince the family that this is different than say, going to the Macy's Thanksgiving Parade or Times Square on NYE - both crowded events as well (and I have no desire to go to either of those anyway).

Thanks! I have been reading about the crowds as well, but my understanding is that there is such excitement in the air that we just can't miss it. I'll have to convince the family that this is different than say, going to the Macy's Thanksgiving Parade or Times Square on NYE - both crowded events as well (and I have no desire to go to either of those anyway).