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Itinerary for summer trip

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Planning a trip for summer of 2025 and wondering if this itinerary is feasible. Please advise if you see any potential issues?

  1. Fly into Florence and stay 2-3 nights
  2. Train to Arezzo, stay 1 night here or move on
  3. Train to Cortona, stay 2-3 nights
  4. Possible day/night in Assisi
  5. Train to Orvieto, stay 2 nights
  6. Rent car and drive to agriturismo in Tuscany and stay a week - day trips to the towns nearby that we wish to see.
  7. We'd like to see Rocca del Leone, not sure if that's doable as a day trip or if we should plan to stay a night near there?
  8. Drive to Volterra, stay 1 night?
  9. Drive to Lucca, stay 2-3 nights (there is a class we want to take here).
  10. Drive or train back to florence for 1-2 nights Fly home.

Trying to limit the length of time we need car to cut down on the expense if possible, as stick shift is not for us, and my daughter will not yet be twenty so I'm aware that'll be extra also. Packing light, a backpack each and maybe a roller bag as we'll be gone nearly a month so need to bring our meds. Stays will be a mix of agriturismo, monasteries and apartments most likely. Our plan is to do only what interests us most in florence and then head for the hills for the rest of our time to enjoy cooking and eating our way through the countryside. Not into tourist trap stuff if we can avoid it.

Posted by
11499 posts

Visit Arezzo and Assisi as day trips instead of changing hotels. Try to avoid one night stays.
I know nothing about Rocco del Leon but it’s on beautiful Lake Trasimeno. We stay in Monte del Lago there.

Posted by
7644 posts

Since Arezzo is just an hour from Florence by train, I would suggest going to Arezzo for your first night. Then save all of your Florence nights for the end of your trip. Stay in the historic section of Arezzo. The B&B where I stayed recommended eating dinner at Antica Osteria dell ‘Agania, and it was excellent.

Posted by
28 posts

Thank you both for your input. We were thinking we'd be too exhausted to do much that first night, thus the reason for just staying where we land for a night or two, then anything we still want to see we could go back for a day trip from one of the places we intend to stay, Arezzo is also within an hour from that place so could be a day trip, but not sure if that would be enough time there. This is our first trip to Italy, and your recommendations and insights are appreciated.

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