This trip we had dreamed for a long time. Idyllic landscapes full of vineyards and olive groves scattered on the hills, captivating medieval towns and excellent cuisine are just some of the reasons why this time we decided not to leave the Old Continent and go to the Italy. We spent a wonderful week in one of the most beautiful parts of southern Europe – sunny Tuscany! For our stay in picturesque Tuscany, we chose the area around one of the most charming towns of the province of Siena – San Gimignano. Below you will find our subjective guide to this beautiful city.

San Gimignano, Tuscany, Italy

San Gimignano – Manhattan of the middle ages

San Gimignano is located on the former trade route between the two main cities of the region – Siena and Florence. The village owes its popularity mainly due to its well-preserved medieval towers (most of it is dated to the 12th century), which used to function as defenses in the time of rivalry between the two feuding parties (gwelfs and ghibellines). According to another theory, the towers were built by rich fabric producers in the period when the city was the main center of textile production and guarded the secret of the yellow dye, obtained from a special variety of saffron. To give the fabric the right color, it was necessary to keep it away from light and dust, and the longer a piece was obtained, the higher the price was received for it (hence probably the need to erect high buildings was born). Once there were as many as 70 towers over the town, but over time their number has decreased, and now we can admire only 14 of them.

What’s worth seeing?

Piazza della Cisterna

Being in San Gimignano it is not possible sooner or later not to be on the lively Piazza della Cisterna. This piazza is one of the two main squares of the city and is distinguished by an interesting, triangular shape. The name of the square derives from the 13th century well located in its center (cisterna), which was once the main source of water for the residents of the city. Around the square you can admire the raw, medieval buildings, such as the 13th-century house of Salvestrini, or Palazzo Tortoli, and the proudly rising silhouettes of the towers of Torre del Diavollo and Ardinghelli. Here you will also find a good selection of restaurants and bars, as well as some of the best ice cream in the world (more info you can find below).

Piazza del Duomo

Heading north-west of Piazza della Cisterna, yoy can reach another charming square called Piazza del Duomo. On the eastern side of the square, there is the 13th-century former town hall – Palazzo Podesta, which is distinguished by a huge loggia and a Rognosa tower rising for over 50 meters.

In addition to medieval towers and historic palaces, in the Piazza del Duomo we can also admire the majestic facade of the collegiate church – Collegiata di Santi Maria Assunta. This cathedral, erected in the 12th century, and then extended by Giuliano da Maiano, is a perfect example of a Romanesque style. The interior of the temple is decorated with beautiful frescoes showing the stories of the New and Old Testament, which were painted by the outstanding artists of the fourteenth-century school of Sienese. Particularly noteworthy are the paintings depicting the life of Christ by Barna da Siena, which can be found in the southern aisle. There are wide, stone stairs leading to the collegiate church, which can not be overlooked. Similarly, as the entire historic center of the city, the church was inscribed on the UNESCO World Heritage List.

Some practical information: visiting the cathedral is possible only at certain times, and a fee of 4 euro must be paid for the admission ticket (details on collegiate church’s website).

Palazzo del Popolo and Torre Grossa

Undoubtedly, one of the most important monuments of the city is the 12th century Palazzo Del Popolo, located near the collegiate church in Piazza del Duomo. This palace, also known as the Palazzo Comunale, i.e. the Municipal Palace, is the main seat of the municipal authorities and is topped with a 54-meter high tower called Torre Grossa, from which unforgettable views of the city roof and the surrounding area spread. This tower was completed in 1311 and is the highest of all the remaining towers in San Gimignano (to get to it, you have to overcome over 200 stairs!). While the ground floor of the Palazzo Del Popolo is occupied by officials, the upper floors include the Museo Civico, with remarkable paintings of Florentine and Sienese artists. In the located on the first floor the Grand City Chamber, also known as the Dante’s Hall (in honor of the poet’s visit in 1300), we can admire Maesta, a masterpiece created by Lippo Memmi, and beautiful paintings depicting hunting scenes.

A handful of practical information: during the peak season (i.e. from April to September) the Museo Civico is open every day from 10.00 am to 7.30 pm. For an entrance ticket, which is valid for two days and includes entry to the tower, we will pay 9 euros.

Where to stay?

Podere Sant’Elena

If, just like us, you are looking for an intimate and authentic atmosphere of the Tuscan countryside, you should definitely stay in the Villa Podere Sant’Elena located southwest of the city, fifteen minutes from the city. Set in the heart of the Chianti region, surrounded by picturesque vineyards and olive groves, this farm stay offers comfortable accommodation with a swimming pool, from where there are breathtaking views of all of San Gimignano. An undoubted advantage of this place are also its owners, Barbara and Marisa, who take care of each of their guests to make you feel like you are on vacation. Every morning, a delicious breakfast is served, consisting of local specialties (such as cheese, sausages, frittata, panini, home made preserves, or excellent extra virgin olive oil), unlimited quantities of coffee and fresh pastries straight from the Gianni bakery (Barbara’s husband) which is located in the city center. What more could you want? 🙂

Where to eat?

Osteria Quattro Gatti

The first restaurant we visited during our stay in San Gimignano was located in a side street on Via Quercecchio Osteria Quattro Gatti. The main advantage of this place, in addition to the excellent Tuscan cuisine, is a quiet terrace where in the shade of trees you can enjoy delicious food. The restaurant serves typical dishes of the region, such as beef tagliata with truffles, rabbit in white wine with olives, or the famous Florentine steak (bistecca alla Fiorentina), and prices for main course vary between 15 and 40 euros. We decided on classic pasta with fresh truffles and insanely aromatic ravioli with spinach in saffron sauce. To this inorganic amount of pecorino cheese (and wine;)) and a recipe for a successful Italian feast ready! We definitely recommend this place.

Gelateria Dondoli

You absolutely can not miss this place. Being in San Gimignano, be sure to try the world’s best ice cream in the located on the Piazza della Cisterna Gelateria Dondoli. And it’s best to go back there a few times 😉 These ice creams are almost a legend (as evidenced by long queues set up in front of the ice-cream parlor), all thanks to the award-winning master named Sergio. Thanks to his experience and inclination to experiments, he managed to create unusual and surprisingly delicious flavors, such as: Crema di Santa Fina (ice cream with saffron and pine nuts), Champelmo (sorbet made of pink grapefruits and sparkling wine), Dolceamaro (vanilla ice cream with aromatic herbs), or our favorite – Vernaccia Sorbet (sorbet from Vernaccia di San Gimignano, the oldest Italian white wine). All ice creams are made of the highest quality ingredients, mainly of local origin, such as organic milk and fruit, or a special variety of saffron, which has been cultivated here for hundreds of years. No wonder that everything tastes so good in Gelateria Dondoli 🙂 When it comes to prices, you will pay 2.5 euros for one scoop of ice cream, two for 3 euros, four for 5 euros and six for 6 euros. We could not control ourselves and each time we left the ice cream shop with four scoops. Afterall, how often do we have the opportunity to eat the best ice cream in the world?

Il Ceppo Toscano

If someone wants to try the king among the regional dishes, i.e. the Florentine steak, he should go to the restaurant located somewhat off the beaten track – Il Ceppo Toscano. This traditional Tuscan dish called bistecca alla Fiorentina consists of a thick piece of delicate beef (usually from native cattle breeds of chianina or maremmana) weighing about one and a half kilograms, usually fried on a wood-burning grate. The meat prepared in this way is bloody, tender and extremely juicy. Meat melts in your mouth! Unfortunately, if you want to taste a good steak you have to take into account a considerable expense. We paid about 75 euros for a half-kilo piece of beef (including bone). For dessert, we tempted on the traditional tiramisu. The perfect end to the evening!

Osteria San Giovanni

Strolling through the historic center of San Gimignano, it is worth going to Osteria located in Via San Giovanni. Some of the tables are set outside, directly on the historic street, thanks to which (especially after dark) we can feel the unique atmosphere of the city. The restaurant, like most of the others, offers traditional Tuscan cuisine, but what distinguishes it from other places is its excellent service. You can eat here for example fettuccini with truffles, famous ribollita, i.e. bean and cabbage soup, or grilled lamb in pea sauce. We for the appetizer decided on beef carpaccio and a tray of meats and cheeses, and for the main course on a saffron risotto. Everything tasted delicious, and we paid 66 euros for the whole. We recommend it!

Ricca Pizza

If, like us, you miss the opening hours of restaurants that are quite unpredictable in Italy (which we have had the opportunity to experience more than once), you can always go for a crispy pizza to Ricca Pizza. The place is open every day from 10.00 am to 9.00 pm, which makes it extremely popular. For a large slice of any pizza that we can take away or eat at one of the bar tables, we will pay 3 euros. For lovers of delicious Italian pizza, a must-visit place!

Palagetto Winery

No trip to Tuscany would be complete without a visit to one of the local wine taverns. Being near San Gimignano, you must go for a wine tasting to the Palagetto Winery. The winery for generations is run by a native Tuscan family and offers a wide selection of regional wines such as Chianti, Brunello Montalcino or the famous Vernaccia di San Gimignano. There are different options for wine tasting, and package prices range from 10 to 16 euros. At a price of 27 euros per person, we can also eat a traditional Tuscan dinner in the form of home-made pasta. In addition to wine tasting, you can also go on an organized tour of the wine cellar. The tour is run by a real expert and includes a visit to the vineyard, cellars with barrels and places for bottling and aging wine. During our visit to Palagetto, for the lack of time we only decided to taste a few selected wines. We left the winery in much better moods and with a few bottles of wine under our arm 😉 Definitely worth it!

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10 months ago

I can’t wait to get out and travel more! and Tuscany is one of those places I’ve always wanted to explore more, so thanks for the inspo!

Katie |

9 months ago

I cannot believe I have never heard about San Gimignano before reading your article! It’s super interesting to discover it with you! And after seeing all of this yummy Italian food I am hungry 😀

9 months ago

I’ll admit I came here for the food. I heard there was ice cream?! Tuscany looks just beautiful but the food looks next level amazing. That gelato – I’m definitely going to have 6 scoops if I go.

9 months ago

This looks like a beautiful part of Tuscany to visit! I’m definitely going to add it to my itinerary when I go back to Italy.

Vanessa Shields
Vanessa Shields
9 months ago

You brought back such wonderful memories! It’s been 16 years since I visited San Giminagno. I remember it being such a quiet and quaint town and so unique for its high towers. Would love to go back and try some of the restaurants as they sound delicious!

Lyndsay Crescenti
9 months ago

This was such a great read! I only spent a few hours in San Gimigiano, but now I feel like I need to go back and stay for a few days!

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