5 days in San Gim...any suggestions?

I will be spending 5 days in Tuscany beginning Oct. 23, I'll be driving...planning day trips to Siena(Sun), Chianti(Mon), Pisa(Tues.), Montepulciano and Montalcino(Wed)...is the trip from San Gimignano to Pisa a full day? Are there any suggestions for intermediate stops, places not to miss or places to eat that will make the trip to Pisa better? Thurs and Friday it's off to Florence...


Well-known member
Spending 5 days in Tuscany in October

Dear LeftyinRoanoke,

it looks like you have a good plan for your vacation in Tuscany ;)

A full day in Pisa depends on you. The most important and famous area in Pisa in Piazza dei Miracoli where the Leaning Tower stands. Visiting this area will take 2-3 hours. Then if you want spend the rest of the day in Pisa you can visit the city center that is very nice. In addition in Pisa there is a great art exhibit about Mirò, if you are interested in art.

Otherwise, if you want to spend just half day in Pisa, you can stop in Certaldo, that is a very nice town with a characteristic medieval center located on top of a hill. Here was born Boccaccio, an important Tuscan writer. Since you like wine you can also stop to Castelfiorentino and or Montaione, where there are many wineries producing Chianti.

If you want to drive to Pisa through a panoramic (but longer) road I suggest you drive to Volterra and then to Pisa by taking the SS68 and then SS439. This way is extremely beautiful offering great landscapes. I recommend you visit Volterra, a great destination in Tuscany. It was an important Etruscan center and its city center is well preserved by big walls.

When you visit Montalcino and Montepulciano I strongly suggest you visit Pienza, San Quirico D'Orcia and other main destinations in Valdorcia. Pienza is renowned for its delicious cheese that you have to taste with handmade jams while drinking wine. ;)

I finally recommend you read our articles for spending two days in Florence and one day in Siena, so that you can find more suggestions.

Don't hesitate to ask any other questions and I hope you'll share your experience with us :)


The Tuscan Expert ;-)
Staff member
Ciao Lefty,

I second the idea about stopping along the way on your day trip to Pisa. I love Pisa so I think you need more than just 2-3 hours to see the monuments in the Square of Miracles - climb the leaning tower, go into the cathedral and baptistery (stay for the sound demonstration, I think it is every half hour - they close the door and sing to show the wonderful acoustics of the place), visit the Camposanto (holy ground=cemetery) with its beautiful frescoes. I found the medieval sculptures in the Museo dell'Opera lovely, they are from the cathedral and seeing them up close is a different experience.

But you can definitely see all this in half a day, so on your way to Pisa do take the scenic route that first takes you to Volterra - spend half a day there walking around the medieval walled town - and then continue on to Pisa for the rest of the day. You can have a wonderful dinner in Pisa at the Osteria del Cavaliere where we had a delicious lunch and then return to S. Gimignano through a faster route in the evening.
Ciao Valentina AND Lourdes!
Grazie mille again! Your efforts are definitely going to make my time in your world soooo much better! Can't wait to come over!

All the Best,



New member
Montaione (florence)

If you want to discover the real Tuscany you must rent a car and discover the lesser-known villages such as Montaione. In Montaione there is the only Holy Mount of Tuscany, San Vivaldo. A religious destination with an incredible heritage of history, art and nature. This is a blog to discover the real Tuscany through the voice of its inhabitants: tuscanyholidaysmontaione.blogspot.com/
Happy holidays , I hope to be useful to you