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4 days in Arezzo , Tuscany

We are staying in Arezzo for 5 nights at the end of June and would like to do 4 day trips.

These two are definites:
One day trip to Florence by train. Best things to see, do and best places for lunch.
One day Montepuliciano by car. Best things to see, do, have lunch.
What are the other best towns to visit the next two days?
I heard Cortona and Pienza can be done in one day?
I also heard SanGimignano was also good.
I would appreciate advice from anyone who has spent time there.
We don’t travel much, and this is our first time in Tuscany.

Thank you so much.
Marie

Posted by
1459 posts

I would advise you leave some time for Arezzo -which is also Tuscany - and take fewer trips.

For Florence check the RS Florence information and one day schedule and adjust as you want. Florence could fill a week so you’ll need to figure out what your priorities are. You may find you want more time there.
https://www.ricksteves.com/europe/italy/florence

Pienza and Montepuliciano are close so they make a more logical day trip together. The long leg from Arezzo will probably take about 1.3 hours so it is at the edge of what I would consider for a day trip. I would add a minimum of 25% to Google driving times when calculating driving times for winding roads.

Cortona is close and can be done by train/bus combo or check on parking before deciding to drive.

I think San Gimignano is too touristy and I would go almost anywhere else instead.

Have great trip,
-Tod

Posted by
8030 posts

Agree with Tod
SG is too far as a day trip and extremely over touristed
Leave at least a day to enjoy Arezzo