Is 10 nights in Italy too short for my itinerary?

This is an itinerary that’s set at a relaxed pace. The key is you’re overnighting for multiple nights in Siena then Montepulciano ( a 60-minute drive) then Florence ( 80-minute drive). Montepulciano to Val d’Orcia is a half-hour drive. Take a high-speed train for the Bologna daytrip from Florence which you can buy now for dates up to September 30 at www.TheTrainline.com
Tickets for the 38-minute trip on a high-speed Frecciarosa or Italo train are currently only $16-$25 each way for dates in July and August. They will rise in price the closer it gets to the train’s departure date.
Trenitalia may have them on sale now as well. GPS in the rental car is a good idea as an option. Make sure you know where the ZTL zones are in Florence ( restricted to locals only and confirmed by transponders) so you don’t rack up tickets.

Are you flying in/out of Florence or Pisa?

It seems doable and not to rushed. Lots of time to enjoy the small towns. Where are you flying in and out of? What time do yo arrive and what time do you leave? Turn in your car upon arriving in Florence. You don't want it in the cities. It is great for getting around rural Tuscany, but it helps to have a navigator for the small rural roads and finding parking. For the wine tasting days it would be best to join a tour or have a guide/designated driver. Siena, Montepulciano and Montalcino are wonderful places to visit.

Sounds like a great itinerary to me. Assuming you're flying in and out of Florence? Everyone's travel style is different but we are doing a somewhat similar trip in the fall. For my work schedule about 12 days in Europe is all I can manage now!

Thank you for the replies everyone! For the questions asked, I will be flying in and out of Florence. I will arrive to Florence about 2 PM day one and I fly out about 10 AM day 11. I will be dropping off my rental car at the Florence train station on day 7 and will not be having the rental car throughout my stay in Florence.

Sounds like a pretty good itinerary, well done for only staying 3 places, but I wondered what are your interests? Seems to be wine, countryside, more wine, HA, & maybe the sights of Florence. Are you booking tickets to some of the Florentine sights, Duomo, Academia, Uffizi? If so, I'm wondering about Bologna, either skip it or to maximize your time, consider a food walking tour, it's really known for it's food! (Use search bar above for Bologna food tours). PS, you asked if this is too rushedt gives you a very good overview of a small area & if you decide to cancel a day trip and put your feet up along the way, you have time.

Forget Bologna and do more in Florence.

Hello everyone - unfortunately we cannot skip bologna. I am going with my mom who made a specific request that she would like to see Bologna, so we're going there

Are you sure you want to drive as soon as you arrive? You'll be tired, sleepy, and jet lagged. Those things might not implact you at all. But for most folks (self included) driving on arrival day is an accident waiting to happen. Don't mean to be Debbie Downer, just offering food for thought.

Hello - I can handle driving upon arrival.

That will work. It is similar to our Tuscany trip, but we stayed in just one location.

Have a great trip!