Final Itinerary for 3 weeks in Italy (Rome, Florence and Tuscany) in September

If you don't know what you want to do in Florence and need suggestions after doing your research you should skip it and not force it; it is unpleasantly crowded nowadays anyway. You are not going to get any suggestions here that you don't already know about or that you couldn't obtain by asking Alexa or Googling "what should I do in Florence".

Florence: In addition to the Uffizi and Accademia,
visit Museo San Marco, a 15th c. convent filled with the works of Fra Angelico and others.

I agree that San Marco would be a good visit. Have you been to Siena before? We loved it and were there 3 nights. Since you don't feel you have enough for Florence, consider staying overnight in Siena. There is a lot to do there beyond the duomo and del campo.

Day 9: Pienza

Explore Montepulciano and Montalcino

Day 10: Pienza

Explore Cortona and Val d'Orcia

In my opinion, you’ll want an entire day for each town and surrounding area. They are in opposite directions from Pienza, after all. The Abbey of Sant’Antimo near Montalcino is worth a visit as is Monte Oliveto Abbey near Montepulciano. You have Val d’Orcia on two days, 7 and 10. You are basically living in it in Pienza so will traverse it quite a bit. Depends on how much off the main roads you intend to explore.

Are you staying in Lucca? It is much closed to Florence than Pienza is so you could day trip from Florence and skip staying there. It is really too far for a day trip from Pienza.

Finally, while is is great to have an idea of what you want to do each day, but give yourself some flexibility. Don’t over commit. You may find things you want to experience you don’t even know about. Also, you’ll need time to relax a bit, enjoy a long lunch and dinner, do laundry. (Insert big grin here)

I am assuming you mean to visit Piazza Michelangelo at DUSK ( not dawn) on just one of these days/weather dependent?

You could add a visit to Mercato Centrale
Have lunch or dinner upstairs

Visit The Bargello museum to see Michelangelo’s David
That museum is rarely crowded

Where/when are you dropping car?

Lucca is too far as a day trip from Pienza
We drove that route (to drop our car in Lucca) all back roads -it took us at least 3.5 hours.

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Are you staying in Lucca?

I'm staying in Pienza

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I am assuming you mean to visit Piazza Michelangelo at DUSK ( not dawn) in jus one of these days/weather dependent?

Yup at Dusk.

You could add a visit to Mercato Centrsle
Have lunch if dinner upstairs

Ok thanks. I will check it out

Where/when are you dropping car?

Florence

Lucca is too far as a day trip from Pienza
We drove that route (to drop our car in Lucca) all back roads -it took us at least 3.5 hours.

After Pienza, I'm going stay in Volterra for 2 days then I'm going to drop off my car. then go straight to Lucca. I'm going stay there overnight

Ok
Starting to make more sense!

Look into dropping your car in Lucca-very easy to do
The rental agencies are outside the walls
No need to go back to Florence
Take train from Lucca to Rome

Could you post your entire itinerary
-where you are staying each night?

Also check your spelling
Ostia Antica

Could you post your entire itinerary

I just posted it. You can take a look at it to see where I'm staying and how many days I'm staying.

Makes more sense to go from Florence when you pick up car to Lucca then Volterra, then to Pienza. Rather than going all the way north and west to Lucca from Pienza.

With that route change- You could even pick up your car as you leave Lucca

Florence 5 nights
Lucca 1 night
Pick up car as you leave
Volterra 2 nights-- does your hotel offer parking?
Pienza 5 nights
Drop off car in Chiusi- (about 1 hour drive from Pienza) right on the train line- then take train to Rome
Or you could drive to Rome and return car there if you are feeling confident
Rome 6 nights

I do like your itinerary- nice choice of places to see, plenty of time and only those 2 short 1 and 2 night stays

Be sure all drivers have an IDP- International Driving Permit

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Volterra 2 nights-- does your hotel offer parking?

I didn't look any agriturismo place nor hotels yet in Volterra.

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I do like your itinerary- nice choice of places to see, plenty of time and only those 2 short 1 and 2 night stays

Thank you

Hi Enryu -
A couple of comments for Florence:
Maybe combine Ponte Vecchio with the Pitti as you'll cross the bridge to get to the palace. IMHO, the best shots of the bridge (if you're a shutterbug) are anywhere but ON it! :O)

Piazzale Michelangelo: Go early enough in the afternoon to head further up the hill to San Miniato al Monte and adjoining Porte Sante cemetery. The church is a very old and important lady, and the view is even loftier from up there. https://www.visitflorence.com/florence-churches/san-miniato.html#google_vignette

Piazza della Signoria: be sure and spend some time with the sculptures in (free) Loggia dei Lanzi. Some of the collection was specially commissioned or chosen for the site to convey deliberate undertones of power/domination, conquest and/or civic pride. The populace created their own narratives depending on the political climate at any given time - such as pro-Medici or anti-Medici - and the same generally applied other imagery placed around piazza. Anyway, two pieces in the loggia in particular, Cellini's "Perseus with the Head of Medusa" and "Rape (abduction) of the Sabine Women" by Giambologna, are masterful works. Look for what's traditionally though to be Cellini's stylized self portrait on the nape of Perseus' neck. :O)

An interesting thesis from a college student on the subject? It's not a difficult read:
https://commons.emich.edu/cgi/viewcontent.cgi?article=1718&context=honors

Yes to San Marco!

Rome:
I'm not sure what rose garden you're planning on seeing but if it's this one (https://www.turismoroma.it/en/places/rose-garden) it's on the Aventine so can be combined with the Orange Garden (https://www.turismoroma.it/en/places/savello-park-or-orange-garden). I don't know as the flowers will be in bloom in Sept, tho. When you visit the orange garden, be sure and visit Santa Sabina next door. It's another really old and important lady! https://www.turismoroma.it/en/places/basilica-saint-sabina-allaventino

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Maybe combine Ponte Vecchio with the Pitti as you'll cross the bridge to get to the palace. IMHO, the best shots of the bridge (if you're a shutterbug) are anywhere but ON it! :O)
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Piazzale Michelangelo: Go early enough in the afternoon to head further up the hill to San Miniato al Monte and adjoining Porte Sante cemetery. The church is a very old and important lady, and the view is even loftier from up there. https://www.visitflorence.com/florence-churches/san-miniato.html#google_vignette

Thank you for all the tips. I will going to visit this post once I arrived in Italy. I really appreciate it.

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I'm not sure what rose garden you're planning on seeing but if it's this one (https://www.turismoroma.it/en/places/rose-garden) it's on the Aventine so can be combined with the Orange Garden (https://www.turismoroma.it/en/places/savello-park-or-orange-garden). I don't know as the flowers will be in bloom in Sept, tho. When you visit the orange garden, be sure and visit Santa Sabina next door. It's another really old and important lady! https://www.turismoroma.it/en/places/basilica-saint-sabina-allaventino

I really like greenery. I'm sure I will going to visit all the botanical gardens or park and just chill over there.