Tours around Tuscany

Beautiful rolling hills filled with olive trees and vineyards. Fantastic art and culture kissing expansive charming landscapes. This is the Tuscan countryside. From the top of the highest points in Siena, Italy we would catch a glimpse of what surrounded us, and we wanted to see more! So, rather than rent a car, we hired our own personal tour guide, Gianni from Tours Around Tuscany. Gianni was born and raised in Siena. He holds a similar philosophy to travel that we like, avoid crowds, and have a unique experience.

Rolling, rolling hills

“Do you have any ideas on what you would like to see with this tour?”

“We like, art, history, food and wine.”

“Great! I know just what to show you!”

And, off we went with Gianni to our first stop at the Archabbey Monte Oliveto Maggiore. It was founded on the initiative of Bernado Tolomei of Siena who chose the rule of St. Benedict as the model for daily life at the monastery. The Benedictine monks have always characterized their days by setting them to the rhythm of prayer, alternated by times of work.  (More on the inestimable contributions of Monks to European Civilization.)

Tuscan Monastery

Eventually it was determined that eating wasn’t considered work, but that they couldn’t also be praying and eating at the same time. So, they developed a rotating schedule where one fellow does not eat during the meal, but spends his time praying aloud for the entire room, while the others eat. Problem solved!

We walked with Gianni through the cloister as he explained the significance of the frescos on the walls. They told about the life of Bernado Tolomei and the history of how the monastery began. Inside the church we saw the most amazing wooden choir benches with an assortment of scenes made out of multi-colored wood slats displayed on the back of the seats. In all of the art we noticed there was one image that kept popping into view. Cats! This was a pet the monks were particularly fond of.

Monastic feline

Wooden works of Art


From the monastery our tour continued to a small village hosting a market. We love a good market! Gianni walked with us explaining what we were looking at. Cheese, fruits, veggies, clothing etc. We left the market with a pound a cherries.

Lovely Tuscan town

Wandering through town we hear small children singing a foreign yet familiar song. We followed our ears and stumbled into a school theater where kids were practicing for their upcoming performance of Snow White. 

“Hi Ho, Hi Ho, it’s off to school we go!”

Except they were speaking Italian!

Italito Snow White

In the next Tuscan village we ascended many stairs. Just as we were about to become winded, Gianni told us the story of a woman well into her 90’s that still climbs the same stairs everyday. Nothing like working out on stairs well into your 90’s to keep you young at heart! At the top was a wonderful view.

As we walked around the streets we saw a funny face cemented on the side of one owners house. This individual found out that his neighbor was spying on him and gossiping behind his back to other members of the village. To make it clear that he didn’t appreciate his actions, he created three cement faces that bore a striking resemblance to his neighbor. He cemented the faces to the side of his house for the entire village to see. It showed his neighbor as a gossip speaking out of both sides of his mouth. Needless to say the neighbor wasn’t very happy and eventually moved out of the village.

Talking out of both sides of our mouth are we?
Talking out of both sides of our mouth are we?

another face

In the next village we ate lunch with Gianni per his recommended choice. Gianni ordered us a sampler plate so we could try a little of everything. A bit of wine, wonderful food, and conversation, followed up by espresso or in my case espresso macchiato. A stain of milk with a shot of espresso. The meal was just as wonderful as the view of the Tuscan countryside from the parking lot. A scene of more rolling green hills that go on for miles at a stretch in any particular direction.


We stopped along the side of the road to view a curvy street used in many car commercials, then headed off to see the Etruscan hot springs in Bagno Vignoni. The Etruscans were believed to be a sea fearing civilization pre-dating the Roman Empire that lived throughout much of Italy. The healing properties of the thermal bath was first discovered by the Etruscans, and later the Romans. The hot bubbling spring water was used for health benefits and relaxation!

Hot springs water flow

Hot springs

Next we stopped at yet another World Heritage Site, Pienza. This city is known as the “ideal city of the Renaissance” It is also famous for its pecorino cheese made from sheep milk. Each year in September a festival is held where locals get together for a friendly cheese rolling competition. Members of each town district compete by rolling a round slab of pecorino cheese towards a wooden spindle. In Sienna they race horses and in Pienza they roll cheese! In addition to cheese this town had the freshest gelato we had ever tasted.

Say cheese

The arena



Our last stop on our tour was the town of Multipulciano. We enjoyed a quick narrated walk through town with instructions to tour a winery. The winery had the biggest barrels of wine I’ve ever seen. At the end was the tasting room where we sampled their version of Vin Santo. It was the most amazing dessert wine I’d ever tasted, and unfortunately we could only buy one bottle. The wine was from 1995 and tasted just like brown sugar. We’re not sure what happened but the bottle disappeared quite quickly after returning to Sienna. 

Medium sized barrels


Bad Denise! That was supposed to sit for 9 more years!
Bad Denise! That was supposed to sit for 9 more years!

The tasting

About Our Tour

Our tour lasted about 9 hours. We were never rushed and our time with Gianni was catered to what we wanted to see. We had great time! Gianni is both an excellent tour guide and driver. We highly recommend contacting Gianni with Tours Around Tuscany for any tour needs around Sienna and Tuscany. Don’t take our word for it just read his TripAdvisor reviews!

Montepulciano in the distance.
Montepulciano in the distance.
Via Dell'Amore!
Via Dell’Amore!

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