I support any of these lol!! I think wherever you go, I'd recommend staying in a little town but have a nice patio/terrace/balcony where you can sit with a little wine or coffee and have a nice view and pick up yummy breakfast, just walking! I haven't been to all of these but Siena, Montelpulcinio, Greve in Chianti, Lucca. We day-tripped to Lucca with our son when he was 12 months and had SO SO much fun!! We loved biking around the wall surrounding the town and people were INCREDIBLY kid-friendly. Lots of kids playing in the square.

Really, any of them would be delightful! Just see what's available Have fun!!

Thirding Siena, but also near Forte dei Marmi is Lerici, Fiascherino, Tellaro for gorgeous ocean views.

Seconding Siena and adding Forte dei Marmi (seaside resort town which would probably be great to visit in September).

Anonymous wrote:I think the Val d’Orcia is nice— you could find an agriturismo there and do some day trips (Montalcino, Montepulciano, Pienza, etc). If you want a larger city Siena is nice— also it a little more northerly so you could visit Volterra or San Gimignano fairly easily I think.

You will want a car but Florence can be difficult to drive in (ZTL zones etc) so consider if there’s an easier place to pick it up (or maybe just pick your rental place carefully).

We really liked this area too- stayed at an agritourismo just on the outskirts of Pienza. We had picked up a car upon leaving Rome and definitely liked having it in Tuscany. Drove around to a bunch of hill towns, including Montalcino/Montpulciano but also a couple lesser known ones. Did a daytrip to Sienna too. We always just left the rental car at a carport outside the town and walked in. Dropped off the car before going to Florence.

Another vote for Montepulciano.

Anonymous wrote:Pienza, Montalcino, Montepulciano, Greve in Chianti, Lucca

Pienza is a great base and they have wonderful agriturismos with owners who can arrange tours and make suggestions. Our two favorite agriturismos are Agriturismo Cerreto and Agriturismo il Macchione, both in Pienza. We have rented cars in Florence at Santa Maria Novella train station with no issues. Just be careful with signs. Rick Steve’s has great driving tips in his Tuscany guides. Just driving around the Val D’Orcia is amazing. September is popular in Italy so make reservations soon.

Agree about Montepulciano, Cortina and Pienza. We got engaged in Pienza.

Pienza, Montalcino, Montepulciano, Greve in Chianti, Lucca

Pienza is a great base and they have wonderful agriturismos with owners who can arrange tours and make suggestions. Our two favorite agriturismos are Agriturismo Cerreto and Agriturismo il Macchione, both in Pienza. We have rented cars in Florence at Santa Maria Novella train station with no issues. Just be careful with signs. Rick Steve’s has great driving tips in his Tuscany guides. Just driving around the Val D’Orcia is amazing. September is popular in Italy so make reservations soon.

Does anyone have a recommendation for a private guide to drive my family to Tuscany for a day trip from Florence? We’d prefer to go on our own (5-6 people) than with a bus, and visit some of the smaller/less touristy places if possible.

Cortona is my favorite. Site of Under the Tuscan Sun.

We love Il borro - great place for day trips everywhere you’d want to go in Tuscany. We rented Villa Casetta. Perfect for family. https://www.ilborro.it/en/accommodation/il-borro-relais-chateaux/villa-casetta/villa-casetta-gallery/

Look at the Dievole resort. It’s lovely. It’s between Florence and Siena.

I think the Val d’Orcia is nice— you could find an agriturismo there and do some day trips (Montalcino, Montepulciano, Pienza, etc). If you want a larger city Siena is nice— also it a little more northerly so you could visit Volterra or San Gimignano fairly easily I think.

You will want a car but Florence can be difficult to drive in (ZTL zones etc) so consider if there’s an easier place to pick it up (or maybe just pick your rental place carefully).

Have done this a few times. We just rented a house between Florence and Siena in a small town and did lots of day trips and were able to cover both of those cities plus a number of small towns. Car is IMO essential.

San Gimignano is a full-on tourist trap that is picturesque but packed full with bus tourists and nothing is authentic. Siena is slightly less touristy than Florence but IMO absolutely worth it. Volterra has some interesting Etruscan history and is off the beaten path and fun. You can also do a (long) day trip to Lucca, Pisa, or some of the coastal resorts. We did this for a day of swimming in the mediterranean because it was so hot in Tuscany and we had our 3 young kids.

Anonymous wrote:Planning a September trip to Tuscany for a week. We will be in Florence for two full days and then want to visit 1-2 other places. Any favorite cities/towns to stay or see, they all look wonderful and am getting overwhelmed. Also wondering if renting a car from Florence is a good idea.

There are no houses in Tuscany.

Planning a September trip to Tuscany for a week. We will be in Florence for two full days and then want to visit 1-2 other places. Any favorite cities/towns to stay or see, they all look wonderful and am getting overwhelmed. Also wondering if renting a car from Florence is a good idea.