We are planning to travel to Tuscany next spring 2020 with another couple. We enjoy art, architecture, beautiful scenery and outstanding food and wine. Our initial plan is to fly into Florence from Miami and stay 2 nights,pick up a car and travel to Pisa via Lucca-1 night, and then stay in Greve in Chianti for 2-3 days or somewhere near there for a home base and explore the country side. Do you think we can also go south of Siena and then go to Montepulciano and other towns in that area? I've always received informed comments from this forum as I'm just starting the planning and would like some feedback

In my opinion, the Val d'Orcia around Pienza is much more beautiful than the area around Greve. If fact, it is our favairite countryside region in all of Europe (that we've visited). It is especially beautiful in April when all the rolling hills are covered in Winter Rye which looks like a green velvet blanket with cypress trese dancing up hills, and a perched village appearing here & there. Here is a photobook from a recent trip.
https://stududley.shutterfly.com/39

Click Full Screen. It takes a while to load. Tuscany starts on page 26. Because of Shutterfly enhancements, some titles & captions are missing or truncated.

Stu Dudley

"Do you think we can also go south of Siena and then go to Montepulciano and other towns in that area?"

Yes, but consider the logistics of your return to the Florence airport starting from the Montepulciano area. If your flight departs in the morning or early afternoon, you'd probably want to drive back to the airport area the day prior, return the car, and the spend the night nearby or in Florence.

Or you might think about reversing your itinerary. Land in Florence, spend 3 nights, take a day trip by train to Lucca and Pisa, THEN pick up the car and drive to Montepulciano for 4 nights. Explore the Montepulciano/Val d'Orcia area and visit Siena as a day trip or along the way to Greve where you'd spend the remaining nights. Greve is about an hour from the Florence airport.

Make sure you understand the "zona traffico limitato" (ZTL, limited traffic zone). Every town you would encounter in Tuscany will have one. Just FYI, Lucca is easy to drive to, but Pisa can be a little nerve-wracking if you're not familiar with driving in Italy. Going to both by train (either order) is very easy from Florence.

https://www.italybeyondtheobvious.co...with-ztl-zones

I was going to say what Jean said--I would certainly be very reluctant to park in Pisa with my stuff in the car, and Pisa and Lucca are easy day trips by train from Florence.

I disagree slightly with StuDudley's comments on the comparative beauty of the Val d'Orcia and Chianti. The scenery in the two areas is just different, and, to me, they are both beautiful for different reasons. More rolling fields in Val d'Orcia. More trees/forests in Chianti. Attractive town architecture in both. Good/great food in both. The local wine is better in the Val d'Orcia (Brunello!), but you can buy/drink the same wine in Chianti. A sense of perhaps fewer tourists in Chianti.

We have not encountered any villages in Chianti that we've loved more than Montalcino, San Quirico, Pienza, Montepulciano, or Monticchiello. Orvieto is only 1 hr from Montepulciano.

We visited this area again in September, 2017 and here is my wife's Shutterfly book from that trip. The Val d'Orcia starts on page 21. Lucca is the first part of the book, and Florence the last (Venice is in the middle).

https://stududley.shutterfly.com/55

Here is my Italy itinerary - Tuscany is in the middle part.

See attached

Stu Dudley