Plan trip to Tuscany: 8May2020 17:00 arrive Rome FCO pick up car rent then proceed to Orvieto (by car about 1:30 hr) stay over night at Orvieto
9 May 2020 visit Orvieto town
-> be sure to do a visit of the underground city, you can pick up you tickets in front of the Duomo (which is awesome)
I am doubtful you will have time to do Assisi in the afternoon - but you could look at stopping by
Sarteano,
Cetona or
Pitigliano before going to Montepulciano - great little towns which are pretty much on the way towards Montepulciano.
10 stay at Montepulciano - visit Arezzo and Cortona
-> this is a full day! start with Arezzo and then Cortona in the afternoon - great views of the valley in the afternoon, in the morning it can be often covered by fog.
11 May 2020 stay at Montepulciano
(remember to leave time to visit Montepulciano they have some amazing underground wine cellars!) and Pienza is close by and definitely worth a stop
12 May 2020 he Val D'Orcia is another region in Tuscany famous for its stunning landscapes and excellent red wines. Gentle hills, dotted with dark cypresses, red poppies and yellow sunflowers make this region the perfect postcard to send back to friends and families. It offers plenty to see, from the medieval streets of Montepulciano to the smaller picturesque towns of Pienza, San Quirico D'Orcia and Montalcino.
I would actually stay the night of the 12th in Siena Then move to San Gimignano stay there for 1 night.
13 May 2020 San Gimignano
From Castellina, cut west toward Poggibonsi to reach San Gimignano, enjoying the drive and incredible views of the countryside on the way, stopping to enjoy the view of San Gimignano's medieval towers before you reach it. Enjoy the rest of the day here, as the majority of visitors leave this beautiful hilltop village as soon as the sun goes down giving you a chance to enjoy a quiet walk through its magical streets and stepping back in time. Make sure to taste the local specialty, the sandy-colored Vernaccia of San Gimignano.
14 May 2020 explore Chianti Starting from the north
(I would start from the south and head north and end closer to San Gimignano),
take the Via Chiantigiana (SS222) and stop in Greve in Chianti to explore its peculiar shaped square and all of the shops in its perimeter. Visit the Wine Museum if you have some time, more for the chance to taste over 200 wine labels of the region than for the farm equipment. Continue along to Panzano in Chianti, stopping to walk along its ancient city streets and take pictures of the hamlet, then on to Castellina in Chianti to walk around the small center and through the city walls.
Vineyards & olive groves in Chianti
I would sleep near Greve, so you can catch the main highway easily on the morning of the 15th for an early start to Bologna.
15May 2020 morning move to Bologna, city tour and enjoy food 16:00 proceed to airport
those are my plan that can be changed, look for your comments and suggestion