Hidden Gems in Chianti and Val D'Orcia


New member

We're a family of four, two adults and two young children going to Tuscany for a week. We'll be staying in a villa in Chianti. We like to slow travel. I need to ask if someone can recommend hidden gems that could include:

i) Wineyards / Olive groves / other places to take a leisurely walk
ii) Places that serve lunch in a garden / grove
iii) Scenic roads / lookouts
iv) Anything else

Thanks a lot!


New member
You can visit:
Pieve di San Leolino
One of the most beautiful religious buildings in Chianti, this Romanesque pieve (rural church with baptistry) is located on a hilltop just outside Panzano in Chianti. Artworks inside the church include a 1421 polyptych behind the high altar by Mariotto di Nardo (1421), two glazed terracotta tabernacles by Giovanni della Robbia, and a luminous 13th-century triptych by the master of Panzano depicting the Virgin and Child next to saints including St Catherine of Alexandria, the patron saint of philosophers.

Castello di Ama
At Castello di Ama, centuries-old winemaking traditions meet cutting-edge contemporary art in a 12th-century borgo (agricultural estate). As well as vineyards and a winery producing internationally acclaimed wines such as 'L'Apparita' merlot, the estate also features a boutique hotel, a restaurant and a sculpture park showcasing 14 impressive site-specific pieces by artists including Louise Bourgeois, Chen Zhen, Anish Kapoor, Kendell Geers and Daniel Buren. This can be visited on a guided tour; advance bookings essential.


The Tuscan Expert ;-)
Staff member
What period of the year will you be visiting? I ask because both areas are well-explored but definitely visiting in the off season can make even some of the same places feel like hidden gems considering the reduced number of visitors.

If you already have a place in Chianti booked for your week, I would suggest starting from there - exploring the roads around that villa you will be able to discover the small wine producers and olive oil makers in the area that cannot be found elsewhere. You will be excited to discover many of them only sell locally and are true hidden gems from the masses, and international markets.

If you ask the place where you're staying at for recommendations of places to ear nearby, you will also discover that there are many restaurants along the roads that offer good country home dishes that are delicious and hidden gems. Many of these places do not ever publicize themselves but are well known to locals - and they are jealous of telling too many people about them, even if they will be proud to share by word of mouth.

As far as scenic roads - my, that's hard because the majority of them are! :D
If you take a look at a map and roads in the area, take the lesser roads across the area and you will have scenic views for most of the time. There are lots of woods in Chianti mixed in the vineyards, and lots of hills.... so you will be exploring areas that one moment seem to be hiding everything and the next moment after a turn or bend discover a breathtaking view.
This is a hard question because the only way to share is to just tell you to drive - and you will find them on your own!
I could send you to specific spots - but those are definitely ones that are not "hidden" and are easy to find.

Enjoy the drives across the area!