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Small Towns Near Florence/ Dolomites

I am going on a 3 week trip to Italy- I am fairly familiar with the country as I lived in Rome for four months and have vacationed there multiple other times.

I will be flying into Milan on May 14 and heading directly south. I have to be in Rome on the 18th but have 4 nights that I would like to spend relaxing somewhere in Tuscany, I won't have a car so it needs to be accessible by public transportation or if the hotel would offer taxi service, I would be okay with that too. I am also open to staying on a family farm/ agrotourismo. I am casting a wide net as I really just want a few magical nights in the italian country side or in a small town. I will be by myself but I am learning italian so would love the opportunity to spend time with locals.

Looking to spend around $100/ per night on accommodation.

I will be in Rome until the 21st with some friends and then heading towards Vienna. I have to be in Vienna on the 27th and would like to spend 3-4 nights hiking in the Dolomites. Again, looking for a small town to base myself in where I can do day hikes out of. Alternatively, I would be interested in staying a refugio for 2-3 nights and just hiking for a few days from there. Not looking to do hut to hut as that is a lot to coordinate and more just seeking some quiet solitude in the mountains.

Would love any and all thoughts- keep on travlin'!

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