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Castellina in Chianti or Cortona?

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3 posts
82 reviews
Castellina in Chianti or Cortona?

Hello, we are renting a villa in Tuscany to spend 1 of our 3 week family vacation this summer. We have narrowed it down to a villa in Castellina in Chianti or a Villa that is 5 minutes from Cortona. We are having a hard time deciding as both villas are great. We will be having a car. Our group is my mother (very active), my husband and our 10 year old son. Any thoughts?

Norwich, Norfolk, Uk
Destination Expert
for Tuscany
Level Contributor
7,989 posts
68 reviews
1. Re: Castellina in Chianti or Cortona?

I'd go for Castellina, it is more centrally based for exploring the region and not as overrun with tourists in summer as Cortona is.

north carolina
Level Contributor
6,048 posts
136 reviews
2. Re: Castellina in Chianti or Cortona?

I think either could be just fine. We have stayed a few times in each area and loved them both. From Cortona it is easy to visit Arezzo, Perugia and Assisi, or further south down into Umbria. From Castellina it is easy to visit Siena, San Gimignano, and all around Chianti.

you can't go wrong either way. I would simply go for whichever villa looks more appealing.

Edited: 12:14 pm, January 23, 2013
Montepulciano, Italy
Level Contributor
5,276 posts
6 reviews
3. Re: Castellina in Chianti or Cortona?

Another vote for Castellina. I love Cortona as a town but a) it's very touristy nowadays in summer (unpleasantly so, I reckon) and b) the countryside 5 mins from it isn't that attractive. The countryside around Castellina is far, far nicer, it also makes a far better base for touring as it's more central plus you can bus into Siena.

Florence, Italy
Level Contributor
989 posts
4. Re: Castellina in Chianti or Cortona?

My vote goes to Castellina too. And I agree with Lastraniera - the countryside around Cortona really isn't much to write home about, while Castellina is right in the heart of beautiful Chianti. There are plenty of good places to eat in and around Chianti (I know, I live in the area) and its really central to the best of Tuscany.

Level Contributor
3 posts
82 reviews
5. Re: Castellina in Chianti or Cortona?

Thanks for the help. Castellina it is, already sent the booking contract!!! Thanks

Plattsburgh, New...
1 post
6. Re: Castellina in Chianti or Cortona?

my husband and I are currently staying in Guercegrossa. We find this perfect for day trips to Sienna, Florence, Perugia and Grosseta. Roma also if you had the time. Even during "off season" we've had much to see and do!

7. Re: Castellina in Chianti or Cortona?

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