Home base thoughts for Tuscany

Many will have great suggestions here, but I think Florence is a great base. Beside a lot to do in Florence itself, the train can be taken to most all these destinations. Sienna is easily reached by coach bus from Florence, and the drop you off in town so no hike from the station. We did Lucca and Pisa as a day trip, going to Pisa first, then Lucca on the way back. Ease day, no driving. You won't want a car in Florence, but you can rent one and do any of the day trips. Volterra is 1 hr. 23 min by car or you could do an organized bus tour.

Last year we rented a lovely apartment by the Duomo and enjoyed every minute of it. Florence is very walkable, and a lovely town. There are so many day trip options from Florence, and you definitely do not want a car there. Hopefully Roberto jumps in here. He gave us wonderful suggestions for our last trip. It was our 5th trip there.

Thank you for your thoughts!! While I definitely want to stay in Florence, I also want to stay in an Agriturismi. I’m just having such a hard time figuring out the order of seeing these towns. Right now just from the map it looks the the most straightforward way would be to start in Florence, take a train to Pisa/Lucca, then take a rental car to Volterra/San Gimignano, car to Siena, then return car to Florence and take a train down to Rome.

My husband and I have done two trips to Italy and have explored Tuscany on both trips. We love staying in an agriturismo with a car and visiting neighbouring towns. On the first trip we stayed just outside of San Gimignano at La Mormoraia. It was beautiful but is now very pricey. We visited the town itself and Siena. Then went on to Castallina in Chianti. On our last trip we stayed in Montepulciano at an agriturismo recommended by RS, La Bruciata. It was reasonably priced and great for families although we did not find the food exceptional. We did the RS driving tour of La Val D'Orcia, visited Pienza, Siena, Montalcino and Cortona. Loved both trips. Beautiful vistas, history, food and wine. Nothing better than a week in Tuscany.

We love all the places you mentioned. We did a Road Scholar Tour that included five nights in Siena, that used it as a base to visit towns in Tuscany. It would be great for Volterra and San Gimignano. Pisa and Lucca are more to the NW of Tuscany, so consider more than one base. Perhaps Lucca as well.

Florence deserves a couple of days and Pisa and Lucca can easily be done as day trips (or one LONG day trip together) by train from Florence. So I would cluster these together as a northern, flat, train connected Tuscany and then southern, rural Tuscany into a another set of days.

Siena is a great town and deserves a day all by itself. Places like San Gimignano and Volterra are both best done by car and are convenient from the area of places like Castellina in Chianti or Siena. We stayed for a week outside Castellina in Chianti among the vineyards and it was great.

The real problem of Tuscany is the size. Southern Tuscany contains great towns like Pienza and Montepulciano, and Montalcino all close together but too far from someplace like Florence to be convenient. With the time you have I would figure out how many days you need in Florence and then spend the rest at a small Tuscan town convenient to other areas you want to visit and choose between northern or southern towns because you really can't have both without hours of driving.

I haven't tried it yet but I've had my eye on the area around Buonconvento. It's a tiny town in essentially the center of southern Tuscany. It has bus and train service to Siena (30 minutes) and is close to the southernr cities - 40 minutes to Pienza. It is a bit far from northern places like San Gimignano. If/when I do the agriturismo thing again it will probably be in this area.

If you even plan to maybe rent a car get all drivers IDPs before you leave the states and understand about ZTLs in Italy before you get there and check ZTL details for everywhere you're going to visit before you go. Also drinking and driving laws in Italy are very strict and just got stricter so plan wine tasting during your travels very carefully.

I say try an urban/rural combo, don't try to do too much and you'll know which one you want more of when you come back.

Have a great trip,
=Tod

An agriturismo is awesome but I wouldn't use it as a "base".

Choose between Sienna or Florence (Lucca is great but it's a but it's on the far northwestern edge of the places you want to visit) and do your base and day trips from there, then go spend a couple of nights at an agriturismo. You can rent a car for just those days.

Month of the year? Does the family fit in one car? Can you drive a standard if they fail to provide an automatic? I think 7-8 days is a lot, but we still haven't been to Pisa in 7 times in Italy, and you did mention not wearing out your family.

We went to just Florence on our first trip to Italy (Rome-Florence-Venice). I don't consider Florence part of a trip to "Tuscan hill towns", and it's too far to the east to be the best base. But your decision for a car or not is a big factor. I don't love renting a car in Europe, but a car lets you visit two or three smaller towns easily in one day. Don't fail to read up on provided-insurance, ZTL, and IDP. We chose a rural luxury hotel (Locanda dell'Amorosa, Sinalunga, but I'm not saying you should stay there) for ease of parking and driving at the start and end of each day. I certainly would not change hotels three times to see Tuscany.

We are not pool-people, but it was so hot in July that we used the pool every evening before our light dinner in the hotel bar. That's because we booked and paid in advance for gourmet, wine-tasting lunches at restaurants affiliated with wineries. Yes, I did have to refuse additional tastings offered, and we did our wine shopping after lunch, or walked around the property for a while.

Certainly Siena is a must-see, but it's a huge city compared to most of the main destinations in Tuscany. Finding Tuscany parking in the summer can be like visiting an American mall in December, driving around and waiting for a space to open up.

You didn't happen to mention Orvieto, which is in Umbria, but it's a (touristy but) really nice visit, and a train accessible place to rent a car. (Have to check on route from train or hilltop to the car rental, we rented in Civitavecchia after a cruise.)

In your case you have enough time to split your stay into two locations.
One could be Florence.
3 nights (2 full days) are probably adequate to see Florence.
Some of the locations you plan to visit, are best visited without a car, using public transportation from Florence. Siena, Lucca and Pisa (the last 2 could be done in one single trip) are best visited without a car due to the traffic restrictions in those cities. They are also easily reachable by train or bus (Siena better by bus).
So, in addition to the 3 nights for Florence, you could add one night for each day trip you plan to take.

Some locations are best visited by car, maybe using an agriturismo (farmhouse) or country hotel or villa.
San Gimignano, Volterra, Monteriggioni, Val D'Orcia (Montepulciano, Pienza, Montalcino, San Quirico, etc.) are more easily done by car. Any location in the province of Siena can be used as a base. If you plan to use a second base in the Province of Siena for that (with a car), you could also visit Siena from there. Just be careful that there are traffic restrictions in Siena, so you need to park outside the historical center and walk in from there. When I go to Siena I like to park at the Stadium parking lot, which is walking distance from everything. There is also parking (including free parking) all around the Medici Fortress. White stripes means free parking, blue stripes means pay or metered parking, yellow stripes means restricted parking, like handicapped (don't park on yellow lines stalls). Save locations in your Google Maps favorites:
Stadium: https://maps.app.goo.gl/zQtcqpkJrjdkEJdo7
Fortress: https://maps.app.goo.gl/jrVHEA2CJaSqhXDQA