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Picking A Tuscan Countryside Town For 5 nights

2 posts
Picking A Tuscan Countryside Town For 5 nights

Hey everyone,

I'm looking for a cool Tuscan town to stay in for about 5 nights with my girlfriend in August. I think we'll likely rent a car from Florence and drive to whichever town we decide on.

Looking to rent a Villa and enjoy the town and it's surroundings, but also plan on relaxing.

Any suggestions would be great!

4 replies to this topic
Montepulciano, Italy
Destination Expert
for Tuscany
Level Contributor
9,425 posts
7 reviews
1. Re: Picking A Tuscan Countryside Town For 5 nights

Not sure what your (or anyone's) definition of "cool" is but almost every town between Florence south to the Lazio or Umbrian border is extremely picturesque, charming, quaint, old, historic with nice restaurants and places to stay. If you are thinking about August 2018 though, I would start doing serious research soon as I am hearing from many people that the best accommodation is already booked up, some until October. Also, note few independent houses will let you rent for less than a week (for many it's two) in August.

Edited: 10 May 2018, 02:26
2 posts
2. Re: Picking A Tuscan Countryside Town For 5 nights

thanks for your reply. i know accommodations are tight which is why I'm looking to book asap. the trip is a bit last minute so i'm trying to do as much research as i can in a short amount of time.

I read about San Gimignano but a lot of the reviews say one day is enough there so i'm a bit worried about doing a week there.

CA
Level Contributor
11,876 posts
3 reviews
3. Re: Picking A Tuscan Countryside Town For 5 nights

I read about San Gimignano but a lot of the reviews say one day is enough there so i'm a bit worried about doing a week there.

Big mistake. It's clogged with tour bus loads of visitors.

Montepulciano, Italy
Destination Expert
for Tuscany
Level Contributor
9,425 posts
7 reviews
4. Re: Picking A Tuscan Countryside Town For 5 nights

Consider somewhere smaller and far less touristy than San Gimignano. The list - as I warned before - is long but a few you may want to check out on-line for starters include: Radda in Chianti, Castellina in Chianti, Montepulciano, Montalcino, Cortona. Others will chip in with many more just to make your life more difficult! Truly, it's a "how long is a piece of string?" type question.

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