Itinerary for Tuscan Hill towns

[Rosalba]

I'll be going to Tuscany in October for 3 days and I need help on planning my itinerary. I'd like to be based out of San Gimingano and I'd like to visit some nearby towns. I was thinking Montepulciano, Pienza, or Montalcino. What are your thoughts? I'd like to explore the countryside, towns and shops. I will be renting a car. Also, is it to far to drive to Cortona for 1 day and drive back? Thank you!

[Lourdes]

Ciao Rosalba,

If your main interest is to visit Montepulciano, Pienza and Montalcino, then San Gimignano is not the best place to stay at since these towns are all in southern Tuscany in an area called Val d'Orcia and you'd have longer drives to get there.
I'd suggest you stay somewhere near Pienza and San Quirico d'Orcia that way you are in between all of these towns - and Cortona is much closer - so that you can visit the area you are interested in. Take a look at accommodation in Val d'Orcia so you can decide where to stay.
You can still visit San Gimignano on one of your three days, that will make it the only time you have to drive further away for a day trip while everything else will be closer to get to.
So you can do San Quirico, Montalcino, Pienza on one day, Montepulciano and Cortona on another and San Gimignano and maybe Colle Val d'Elsa or Monteriggioni or even Siena on the third day.

I am sure you'll love Tuscany, do let us know if you have any other questions!

[Rosalba]

Thank you so much, Lourdes. I thought the same after submitting the post and doing some more research. I really appreciate all your suggestions...I feel much more at ease, since I will be traveling solo and felt a little overwhelmed when I was first deciding exactly where in Tuscany I want to visit. Thanks again!

[Lourdes]

I am sure you'll do fine and love every place you end up visiting! If you have any other questions, don't hesitate to ask!

[soohoot59]

I agree with Lourdes!!