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Road Trip 6 days in Umbria/Tuscany region

Husand and I are going on a 35 day trip to Italy
5 nights in Rome
4 nights around Amalfi coast
5 nights around Umbria/Tuscany with rental car (need help with this part as to where to go and stay)
3 nights in Florence after dropping off rental car in Siena
3 nights in Bologna
3 nights in Venice
4 nights Dolomites with rental car
3 nights Lake Como with rental car
2 nights in Milan (dropping off rental car)
2 nights in Ostia Antica

I need help as to a good homebase and road trip route around the Umbria and Tuscany area. I've researched and there's a long list of cities, but husband and I only have 6 days 5 nights. We would love to take a cooking class and may be stay at an agriturismo (?) or two?

Posted by
29 posts

That sounds like an amazing trip! Perugia looks nice from YouTube videos that I've seen. Good luck with the planning. Cheers.

Posted by
1869 posts

Our trip is next month, but I can share what I booked after extensive research...
I booked three nights in Siena at Hotel Ravizza and three nights in Pienza at Hotel Gregorio. Both offer parking. We like being in a town in the evenings where we can walk to dinner, but enjoy leaving for road trips during the day. While in Siena we will visit Volterra and San Gimignano one day, the Chianti villages the other day. When we leave Siena we will stop briefly to leave our luggage in Pienza, then head down to Civita Bagnoregio and stop at Cetona on our way back to Pienza. One day in Pienza we will explore the Val d'Orcia region and the other villages in the area. The other day we will drive to Cortona (Under the Tuscan Sun location) . Instead of Pienza you might also consider Montepulciano. None of these towns / villages are very far apart but of course the roads are slow.
Hopefully, this will help you with your planning.

Posted by
417 posts

When I did a road trip around Tuscany I stayed in Siena and Montepulciano and loved both locations as home bases. I would highly recommend visiting Volterra, San Gimignano, Montalcino, Pienza and Assisi. Any other small towns that interest you will also be worth it. Give yourself time to do the drives listed in the RS Tuscany guidebook. The one between Siena and towns to the south has the best views.