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Toscany for 4 days

Our party of four women will be travelling through Tuscany in early May 2019 ( May3-7). We have already designed a day in Florence. We will be renting a car and staying at Borghetto Tuscan Holidays in San Gimignano. We are thinking of visiting Sienna, Montalcino, Montepulciano, possibly Assisi, Orvieto. Basically, we would follow the Heart of Tuscany drive designed by RS. What should we not miss, must sees, anything off the beaten path, particular vineyards, anything you can think of?
Thanks in advance.
Evelyne

Posted by
4105 posts

Have you checked travel times to Assisi? It could take you 2-2 1/2 hours.

Siena will take the better part of a day. You could combine it with Montereggioni which is close by.

I would do Montepulciano and Montalcino one day in that order. If you have extra time, you could add Pienza in between.

On your last day head to Orvieto if Rome is your next stop, traveling thru the Val d'Orcia. Do you fly out of Rome?

Posted by
44 posts

Thank you...this is very close to the plan I had in mind. Nice to confirm.

Posted by
11 posts

If you have time, Volterra was hands down our favorite hill town. It was less busy, even in July when we visited two years ago. Less touristy than Orvieto (even though Orvieto was great)

Posted by
44 posts

Yes, thanks. I know that Rick speaks highly of Volterra in his book. We'll ad it to our itinerary. Thank you.

Posted by
11156 posts

Assisi and Orvieto are in Umbria not Tuscany and are too far when there are so many charming Tuscan villages nearby that you can visit.
The historic SR 222 goes from Siena to Florence and you can visit Siena, Greve, Panzano, Castellina, Radda and more. They are surrounded by vineyards. The highly recommend this route and have stayed in this area many times.
Yes, include Volterra too.
Save Umbria for another trip.

Posted by
44 posts

Thank you. We will see Orvieto on our last day on our way to return our car to Civitavecchio.