My Italy in 10 Days Day 6 Touring Toscana, Part 1. San Gimignano, Montiriggioni and Wine Tasting

So, in the previous post I had told you that I planned a day trip to Tuscany, from Florence. By planned I mean instant plan, a kind of fast food planning. I did not want to book in advance as I was not really sure where to go, and how to fit it into my plans, so I bought it the day before, upon arriving in Florence from Venice. It costed me 53 Euros, which included the bus, guide, 3 course lunch at a winery, wine tasting and visit to San Gimignano, Montiriggioni and Siena.
The tour company offered to pick me up at the hotel at no extra cost, making a point to tell me that I should be outside the hotel at 07h40 sharp. So there I was, with a chilling 12ºC  that I did not expect at all, shaking, and waiting. And waiting, and waiting. Finally after 20min of wait a small van came and I was already furious because I could easily have slept more (yeah, sleeping is a hobby of mine). However, how could I resist the charming English with a strong Italian accent of the driver? “Good móhhrrning Dálila, and wélecome” So in I go, and there we go to pick up some people and then head to the meeting point at Santa Maria Novella train station. Getting there, oh gosh, a sea of people in a long queue, in a very disorganized manner, for the tour. I ended up understanding the it was the departure point of several tours, and to be able to identify which one you were in, we were given self adhesive circles in different colors. Mine was the white circle, corresponding to a particular guide and bus. So in the bus I go, and luckily got a window seat.
Upon departure our guide briefed us on how the tour would be, how the audio equipment worked and what the tour would consist of. She spoke a very good English with a lovely Italian accent.
The first stop would be the medieval San Gimignano, an hour’s drive from Florence, with 90 min free time, then, late morning we would go to a family winery, where we would have wine tasting and lunch. After lunch we would go to Montiriggioni, where we would also have free time (45min to 1 hour) and then finally  Sienna, considered the second most beautiful town in Tuscany, with the world-famous Piazza del Campo square, where there was a guided walk, followed by 90min of free time.
So all happy I go, in a smooth bus drive, with beautiful views soon after leaving Florence.
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First glimpse of the Tuscan countryside
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The beautiful view, with rolling hills, the olive trees and vineyards, so typical of Tuscany
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Just breathtaking
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Arriving in San Gimignano – Porta San Giovanni

So, the first stop. San Gimignano. San Gimignano is a medieval small town declared by UNESCO as a World Heritage Site. The city is enclosed in walls dating back from the 13th century.  When you climb the hill there (as the bus stops down below), nothing prepares you to what you will see and feel: a true travel in time, back to the medieval times (if it wasn’t for the loads of tourists, as, there were at least 5 buses approaching at the same time). San Gimignano is called the town of the hundred towers; in fact it used to have 72 towers, of which 14 are still standing. The towers were also the house of rich merchants and financiers of the aristocracy, who in fact competed to see which would have the tallest tower, as the height was directly related with the power and money, marking the difference between the different families.

Archaeological findings, mostly from tombs determined that around the 3rd century BC, the Etruscans settled in the town, followed later by the Romans, who named the town Silvia. The present name is in honor  of  Saint Geminianus, the holy bishop of Modena, that, according to the tells, freed the city from the Huns.

In the Middle Ages and during the Renaissance the town used to be a stopping point for Catholic pilgrims. San Gimignano is also famous for a white wine, contrasting with a region so famous by its red wine, the Vernaccia wine. The Vernaccia is the first Italian DOC wine, and is one of the oldest wines of Italy, that was already mentioned by Dante in the Purgatory (I told you before I am fascinated by Dante right?), and was a favorite of Lorenzo de Medici – Il Magnifico. In 1300, San Gimignano hosted Dante in his role as ambassador for the Guelph League.

Sì disse prima; e poi: “Qui non si vieta
di nominar ciascun, da ch’è sì munta
nostra sembianza via per la dïeta. 18

Questi”, e mostrò col dito, “è Bonagiunta,
Bonagiunta da Lucca; e quella faccia
di là da lui più che l’altre trapunta 21

ebbe la Santa Chiesa in le sue braccia:
dal Torso fu, e purga per digiuno
l’anguille di Bolsena e la vernaccia”.
(Purgatorio, Canto XXIV).

The development of the city was heavily influenced by the production of saffron, since the middle ages, as a medicinal herb and also used as colorants. Saffron, is cultivated on the hills that surround the city and highly priced in the different markets worldwide.

As soon as I passed the medieval wall through Porta San Giovanni or Porta Fiorentina, into Via San Giovanni, I was wowed, it was just incredibly beautiful, almost magic.

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Via San Giovanni
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A small alley with the typical stone buildings
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This small lateral road leads to a fantastic view over the rolling hills of Tuscany

Going up Via San Giovanni you see on your right hand side (after a series of souvenir and deli shops), a church, today no longer serving it’s purpose and being another deli shop – Chiesa de San Francesco that dates back to the 13th century.

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Chiesa de San Fracesco – St. Francis church
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Museo Torture – de Pena de Morte

I was thirsty and in desperate need of a coffee, that I had standing in a small cafe close to the torture Museum, before heading to the Grossa Tower, the highest tower in San Gimignano.

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A capuccino with pana per favore. Grazie
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Torre Grossa
Torre Chiggi  and Torre Rognosa
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Torre Grossa

It was now time to climb the Torre Grossa, located in Palazzo del Popolo or Palazzo Nuovo del Podestá, the only tower that is possible to climb in San Gimignano. The palazzo hosts the Civic Museum.

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Entrance to Torre Grossa
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Beautiful details

After climbing the 54 meters, and reaching the top I was breathless, not because of the stairs, but the view, oh my gosh, what a view. 360º view over the Tuscan countryside and the whole San Gimignano. Something to contemplate, to breathe deep, to awe, unforgettably.

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Panoramic view – Tuscan Countryside
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Torre Rognosa
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Torre Chiggi
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Torre del Diavolo at Piazza della Cisterna, Palazzo Tortoli
Torre Cugnanesi

After some time contemplating the beautiful views and the sense of calmness it gave me, was now time to descend, and I decided to visit the Duomo-  Collegiata de Santa Maria Assunta, as there was still plenty of time available. It is a very humble building located in Piazza del Duomo, and nothing prepares you to the rich and beautiful interior.  It is a Roman Catholic Church, famous for its paintings, which include works of Bartolo and Ghirlandaio.

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Torre Salvucci and Torre Pettini, Piazza Del Duomo
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Duomo di Santa Maria Assunta

As you enter the Duomo, on your right hand side, you will find a fresco dedicated to the Old Testament, and on the left hand side the New Testament.

The frescoes of the Old Testament were painted by Bartolo while the New testament is polemic and there is no documentation to allow certainty regarding the author.

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The beautiful interior
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The beautiful frescoes – Do you believe all of them are originals? Wow, just wow
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The frescoes – the details, the colours still so vivid
Being awed at the surrounding beauty
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Panoramic of Piazza del Duomo, Palazzo Podesta on the right

Exiting the Duomo I stayed for  some time looking at Piazza Del Duomo and the amazing vibe surrounding it and then headed to Piazza Della Cisterna to see the gelateria that was considered the best in the world, with several international awards. There was a cue as usual, but worth the waiting time as the gelato is truly good. They have original flavors like saffron and pinole and the Sorbeto di Vernaccia that honors the famous wine.

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The famous gelateria

After Dondoli, I walked around the city, and ended up in the Ornithological museum

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Walking around

The ornithological museum holds a collection that dates back to the second half of the 19th century. The place was in the past the church of San Francesco, dating back to the 16th Century..

The impressive collection
Charming houses
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Walking around

As I was running out of time, I headed back to Via San Giovanni and went to a beautiful deli store to buy olive oil, salami and wine.

It was now time to get back on the road, as our tour was taking us to the wine tasting and lunch at a local Chianti Classico winery. The bus drive there was smooth and the landscape beautiful. A glorious day, no sign of rain, warm and perfect for the tour.

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Entering the winery

The chosen winery was Casa Frassi, a agritourism house in Chianti, producing Chianti Classico wine, extra virgin olive oil, grappa, salami of Cinta Senese. A beautiful place.

I must confess I had high expectations for this wine tasting and lunch, but to be honest it quite disappointed me. Maybe because (again) there were 2 fully packed buses arriving at the same time, the win tasting was brief, fast, and the amount given was very small. The three course lunch was not of the best quality also, and I had just the antipasto (the second course was pasta with a ragu, small serving, and lots of pasta short on the ragu. It was worth the experience and the beautiful place but next time I will drive through Tuscany and will do a wine tasting on my own. large groups make it too impersonal and you will not enjoy the experience if you did have set high expectations as i did.

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Wine tasting prepared
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Waiting for the tasting
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Tasting Chianti Classico
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Details of the winery
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The main house (the place is also a hotel)

Soon we left, heading to Montiriggioni and Sienna, again beautiful surroundings and breathtaking views all the way there.

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On the way to Montiriggioni
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Boom, after a curve on the road, there is the beautiful medieval Monteriggioni

Montiriggioni suddenly appears after a curve of the road, with its city walls still so well preserved. It was built in the early 13th century and soon became a military post aimed to defend Siena against the Florentine invasions. The entrance is made through Porta Franca or Porta Romea. It is a very small village and soon after entering you get to the main square: Piazza di Roma, with the Church of Santa Maria Assunta.

Porta Franca
Entering the village


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Piazza di Roma and Chiesa Santa Maria Assunta
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A charming restaurant
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Typical stone houses

Montiriggioni was cited by my crush (lol) Dante Alighieri in his most famous work, Divina Comedia or Divine Comedy:

“però che, come su la cerchia tonda
Montereggion di torri si corona,
così la proda che ‘l pozzo circonda
torreggiavan di mezza la persona
li orribili giganti, cui minaccia
Giove del cielo ancora quando tuona

As with circling round
Of turrets, Monteriggioni crowns his walls;
E’en thus the shore, encompassing the abyss,
Was turreted with giants, half their length
Uprearing, horrible, whom Jove from heaven
Yet threatens, when his muttering thunder rolls.”
– Dante Alighieri, Hell, canto XXXI, lines 40-45

What makes Montiriggioni really special is its wall façade, which is still the original dating back from the 13th century, and is considered one of the most well preserved and fortifications in Italy.  The walls are made of large blocks of stone and have 14 towers and two gates. Paying a small fee it is possible to climb some sections of the walls and have a panoramic view over the surrounding areas (which I did not have the time to do).


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Walking around
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One of the Portas
Wandering around
Back to the entrance
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The beautiful surroundings
Getting back to the bus
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Getting to the bus
The view from the parking lot

The visit was quite short and our guide was repeatedly asking us to return to the bus, in spite of still having 30min according to the program. So it was really a quick visit, but enough to leave with the idea that Montiriggioni is a great place to visit.

It was time now to go to Siena, and it will be the theme of next post.

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Getting to Siena

Passionate about the ketogenic and lowcarb lifestyle, solo traveler, passionate about helping people achieve their dreams. Amateur photographer, recipe developer, creator of the famous keto perfect bread.

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