Florence, ct, Tuscany, Rome itinerary help

La Spezia would be the place to pick up a car upon leaving the CT.

To me it looks like you have too many places for the amount of time you have.

You are really shortchanging Tuscany! It would be very worth your while to add more time. Your flight cost and efforts will be the same but you would have a much better experience. Our first trip to Italy was two weeks- Rome, next Florence then rural Tuscany staying in Chianti region in Castellina, , ended in Venice. It was wonderful. You are cramming too many places into too little time. Your first day you will all be jet lagged.
Pick up car in La Spezia if you keep the CT in your itinerary.
We often return rental cars at Rome FCO, taxi or train into Rome. With four people a taxi with fixed rate of 48€ from FCO to city center would be a better option.

Would this be a reasonable mix of towns to see in 2-3 days?

You don’t have 2-3 days. A 2 night stay means you have 1.5 days. By the time you pick up car and get on the road from La Spezia it’s probably getting close to noon. It’s at least a 2.5 hour drive to Siena (note spelling). That leaves you just that evening to enjoy Siena, then next day could be a day trip to Volterra and maybe San Gimignano.
Each of the hill towns you have listed needs a good half day- getting there takes time, finding parking, etc.
What will you do with your luggage in the car?
Make sure it can be hidden from view if you are stopping en route.

Orvieto is a long drive from La Spezia- but it does have a Hertz location so if you rent with Hertz you could drop car there and train to Rome.

I think you are trying to fit in too much and are cutting everywhere short.
A 3 night stay in Rome is only 2.5 days to enjoy the sights. You'll lose at least a half day just getting there from wherever you have stayed in Tuscany.

I’d pick either CT OR a Tuscany hill town and give that choice 3 nights. Give Rome 4 nights.
You only have 10 nights- 4 changes in location is a very fast paced trip with little time to see much more than the highway to and from. It will also be brutally hot.

You could head to Siena from Florence- easy by bus or train- stay there and rent a car there for a day trip, returning car in Siena as well. Then train to Rome.

It will also be brutally hot.

Repeating Christine Hs warning for emphasis. And it will be brutally crowded, especially in CT with the cruise crowds. I will agree with the recommendation of dropping either CT (my pick) or Tuscany, and adding those days to Rome and the remaining middle stay. Also consider picking a rather central Tuscan town for all your nights there, and doing day trips with the car. Less packing and schlepping of bags. And no risk of theft in an unattended car.

To appreciate Tuscany and Umbria you need to sleep one night in Lucca, one night in Volterra, one night in Siena and one night in Orvieto. You also need four nights in Rome if you include Vatican City.
You could add a night in Florence and take a direct bus from Florence to Siena (1h 15m) as a day trip. Do not take the train because that takes 1h 30m and you need to take a bus from Siena's train station to Siena's old town. Don't expect a taxi to be waiting either.
If you hike in the Cinque Terre in the morning and spend the afternoon at the beach in Monterosso add a night so you have one day to explore all five towns and another day for hiking and swimming. You can then take a train from Monterosso to Rome’s Termini station (4h 45m) that requires a change.
If you want to see more of Tuscany and Umbria assume you’ll return.

We’ve used a rental car in Italy, including driving to Cinque Terre plus out-of-the-way spots in Tuscany and Umbria last year, as well as around Castagneto Carducci in Tuscany this year. After a week with a car this year, we turned it in and then spent a month seeing more of Tuscan cities and towns by train. The places you mentioned are major enough to be easily reachable by train, but maybe you want a car for flexibility, or for scenery along the way? Maybe (I’m not sure) the car would be cheaper for the 4 of you, compared to train tickets, or not. Some of our train rides required changing trains in stations along the way, to reach the ultimate destination. But have you considered traveling by train after your C.T. time?

In Lucca two months ago, we stayed several nights at Rick’s recommended La Boheme B&B, and it was a pleasant place except for the Friday night we arrived. Fridays seem to be the one night the old town is mobbed with visitors, noisy visitors, and they were still walking the streets and carrying on loud conversations well past 2AM. We slept much better the remaining nights.

Our schedule wound up leaving us just one night in Siena, and we really needed at least one more night and another day … if not even more. If you’ve got just the 2 nights before Rome, I’d stick to the western edge of Tuscany, and see and/or stay in Lucca and perhaps Volterra. Pisa’s not possibly on your list for a short visit en route, right? It was a great stop one day for us,.

Orvieto could make for a very nice day and night, but then where else would you stay? Second night in Orvieto (perhaps), or a too-short Siena the other night? And then you’ve got a longer drive than necessary, just to reach Rome, when a train ride would get that done. Or turn in the car at Orvieto, then do the train? Turning in at the Rome Fiumicino airport requires driving south past Rome, then backtracking to get into the city.

Thanks for all the feedback. Just to be clear, I’m not looking at visiting all those sites in Tuscany, they are just possibilities. Since with this itinerary I need to travel from CT to Rome, and have allocated 2 nights, thought we might see a Tuscan town or two. I’ve located a nice agriturismo in Chianti near Siena. If we wanted to day trip, could visit it during our two night stay. If not, we could relax at the agriturismo by the pool (:

Trying to see where the best spot to stay a few nights in Tuscany en route to Rome would be.

The agriturismo near Siena would make a nice stop and Siena is worth a day trip. This way you get to enjoy a stay at an agriturismo and the medieval town Siena. Both Lucca and Siena are easy day trips from Florence and Orvieto is a good day trip from Rome.

I’ve located a nice agriturismo in Chianti near Siena.

Be aware there are usually minimum stays at agriturismos during the height of tourist season.

Have you traveled in Europe before? I'll foot stomp what others have been saying, you are trying to do way too much in too little time. By trying to see everything, you'll end up seeing nothing. You are also moving around a lot. You should consider how much time is eaten up just be checking in and checking out.

Your 3 nights in Rome is just two days. Sit down and write a detailed itinerary and you'll quickly see how hectic your proposed itinerary is.

Also, before thinking about visiting CT at the height of tourist season, check this out.