Italy trip - Florence, Siena and Rome in Oct

Florence: My favorite is Michelangelo’s drawings at the Medici Chapel. Tickets sell out fast and it looks like they are now booking for December. I’m adding the link in case something opens. You can’t walk up and go in. https://webshop.b-ticket.com/webshop/webticket/timeslot?tsproduction=68

Uffizi is worth a visit. I gave it two hours and was there for four. https://www.b-ticket.com/b-Ticket/uffizi/default.aspx.html
Scroll down if you want a five day pass which includes Pitti Palace.

Sorry that I don’t have restaurant recommendations. Eating Europe does an evening food tour if you are interested for one night.
https://www.eatingeurope.com/florence/

Have a great trip!

Question? You need 3 nights for 2 full days of sightseeing; 2 nights only gives you 1 full day + some odd hours. Could you share your full itinerary, such as where you're coming from before Siena and picking up the car; where you're dropping it off, where you're coming from before Florence (if not Siena) and where you're going after ? Actual dates could matter as well. TIA!

Adding the full itinerary. We are doing 4 days in Swiss before Italy

Oct 13 Florence - Swiss to Milan train. Then Milan to Florence train. Stay in Florence
Oct 14 Siena - Taking the rental car from Florence to Siena
Oct 15 Siena - Day trip - Tuscany
Oct 16 Florence - Drive to Florence - Drop car.
Oct 17 Florence - Academia gallery booked
Oct 18 Rome

Oct 19 Rome

Oct 20 Rome

In Florence, we really loved the Secret Passages tour at Palazzo Vecchio. It's fascinating!

You didn't mention Piazzale Michelangelo, but it's a lovely view over the city. I'd actually consider going in the evening, as it's not crowded and the lights over the city are beautiful. Might be a nice place for a little birthday toast :)

Piazzale Michelangelo is a great view of the city you can walk if you're up for it or take a taxi. Sunset there is beautiful and seeing the Duomo from that perspective is iconic. I took a bike up most of the way and walked the rest when I was there.

I would recommend visiting the Uffizi Gallery on the 2nd day if you are interested in art history. Some of the best collection of Renaissance art in the world. My family really enjoyed it earlier this year. The Vasari Corridor also reopened this year but I believe you have to book that in advance. The Accademia and Uffizi Gallery, I do recommend a guide since there is so much history. We had an excellent guide with The Tour Guy. However, I was not impressed with our tour guide with Walks of Italy, she ruined our experience.

For lunch La Ménagère is a really neat spot in Florence (the coolest in my opinion). It used to be a hardware store but now is a cafe, coffee shop, and sells flowers.

Caffè Concerto Paszkowski is also a good spot, it's good for people watching on the square.

You have a half day at most on your first night in Siena, then just evening on second day
See the Duomo and Campo on the day you arrive in Siena
Day trip on next day (consider dropping car in Siena this evening (ck hours) and just take the bus to Florence next day

Confirm your Siena lodging has easy to access parking or have your parking figured out

Make sure all drivers have an IDP-required by law and do your homework on driving in Italy-ZTLs, speed cameras, parking

Be sure you have directions in and out of Florence for car pick up/drop off that avoid ZTLs
(Lots of threads here with that info)

You might also consider just staying in Florence 5 nights rather than 2 hotel changes
Rent car for day for your Montepulciano etc visit
Another day take bus to Siena

Be sure when you pick up the rental car... hopefully at the airport that you go directly to the freeway and do not get caught up in the zones where you can't drive. Also... Siena is rather confusing so be sure you have parking at a hotel figured out. I tried to drive there a few times and could not figure it out! Eventually, I just took the train from Florence to Siena.

You really don't have much time to drive around and enjoy the countryside of Tuscany, so you might want to try and add a day here.

Need way more time in Florence. Just doing Accademia, the Uffizi, the Doumo and San Croche takes more than you have planned.

In Siena climb the famous tower at the main square.