Dear Traveller friends,

Today we are going to discover two of the most fascinating towns in Tuscany, halfway between Florence and Siena.

If you are touring Tuscany or find yourself in this area for some reason, you can’t possibly miss a visit to these two places.
San Gimignano is renowned all over the world as the “town of 100 towers”, and it’s one of the eight UNESCO World Heritage in Tuscany.
Certaldo Alta, less famous than San Gimignano, is nonetheless an unmissable stop. Its medieval hamlet is so well kept and polished that it’s considered one of the most beautiful hamlets in Italy.

If you decide to enjoy these two attractions, you should start with Certaldo Alta. The visit will take not more than a couple of hours. Then you’ll be able to devote the rest of the day to San Gimignano, where the tour requires more time.

My suggestion is to find somewhere to spend the night in San Gimignano. In the evening, when most of the tourists go away after their daily tour, you’ll be able to enjoy the magical atmosphere of this hamlet without the crowd.

Certaldo Alta

Certaldo is a village split into two parts—Certaldo, situated in a plain, and Certaldo Alta, on top of a hill. Since the area is accessible to residents only, you can’t reach Certaldo Alta by car. In any case, finding a parking lot would be extremely difficult. The best solution is leaving your vehicle in Certaldo, in Piazza Boccaccio or in Via Nino Bixio. You can reach Certaldo Alta by the funicular railway or, when it’s not in service, by shuttle bus leaving from Piazza Boccaccio. However, if you prefer, you can walk up the hill. The ascent is not particularly long nor extremely difficult—with a ten minutes walk, you’ll reach your destination.

Certaldo Alta – Photo Credit: Andrea Gigliotti

Besides being a beautiful hamlet, Certaldo Alta is known for its bond with Giovanni Boccaccio. It’s not clear if Boccaccio, one of the most influential writers in Italian history, was born in Certaldo. What is sure is that he lived there for more than a decade, until his death.

The main points of interest are situated in Via Boccaccio, the centre of the medieval hamlet. However, don’t forget to walk along the other alleys to fully get the atmosphere of the place.

The most iconic building in Certaldo Alta is Palazzo Pretorio (Praetorian Palace). Built around the XII century, this building was crucial since the XV century, because it was the domicile of the Vicar designated from Florence to rule the city. Many were the vicars who occupied the place during the centuries. This is proven by the crests of their families, carved both inside and outside the building.

Palazzo Pretorio – Photo Credit: Andrea Gigliotti
Palazzo Pretorio – Photo Credit: Andrea Gigliotti

You can take a tour of Palazzo Pretorio and admire several frescoes and many Etruscan and Roman findings. These findings are proof that the hamlet dates back way earlier than the Middle Ages.
If you are interested, you can buy a cumulative ticket and visit Palazzo Pretorio, the Museum of Sacred Art and Boccaccio’s House.

If you are touring Tuscany, you might not be interested in sacred art, at least not after visiting Florence and Siena and their masterpieces. However, Boccaccio’s House is worth a visit. Here you can deepen your knowledge about Boccaccio’s writing. From the first floor, you can access the stair that climbs up the tower. From the top of the tower, you’ll be able to admire a 360 degrees view on the hills surrounding Certaldo.

Panorama da Casa Boccaccio – Photo Credit: Andrea Gigliotti

Once your visit of Certaldo Alta is concluded, you can go back to your car and head towards your next destination—San Gimignano. Along the way, more or less 15 km up and down the hills, you’ll be able to see the towers of San Gimignano, standing out against the sky.

San Gimignano

San Gimignano is one of the most famous places in Tuscany. It’s an imposing hamlet part of the UNESCO World Heritage sites.

Since its great popularity, you can expect a high number of tourists crowding the streets, from the first sunny days in Spring until Winter.
That’s why spending one night in San Gimignano can be your best option. Most of the tourists tend to leave before dinner. So, if you stay for the night, you’ll be able to enjoy the unique atmosphere in the evening without being surrounded by a crowd of tourists.

If you want to stay in San Gimignano, Palazzo Mari is an excellent solution. It’s a comfortable and elegant facility in the heart of the centre and near the parking P3 (Bagnaia).

Whether you decide to spend the night in San Gimignano or not, you can’t access the city centre by car. You can leave it in the parking P3 or P4 in the highest part of the hamlet, or in the parking P1 and P2 in the lower part.
Starting from the highest part, your visit of San Gimignano develops mostly along a single street—Via San Matteo—which becomes Via San Giovanni towards the lower part. In these two streets resides most of the main attraction and commercial activities.

Via San Matteo- Photo Credit: Andrea Gigliotti

The exploration of San Gimignano begins in Piazza Sant’Agostino (St Augustine Plaza), where you can find the namesake Gothic church, built in the late Thirteenth Century. After a quick visit, you can head towards Via San Matteo. The street begins with a slight incline leading to Piazza del Duomo (Dome Plaza), the heart of the hamlet.

Palazzo Comunale – Photo Credit: Andrea Gigliotti

Here you can find several attractions. The best solution is buying the cumulative ticket which allows you to access the main attractions in town for 13 euros only. You can buy it inside Palazzo Comunale, the first unmissable stop in your tour of San Gimignano. This building, in fact, is renowned for the Sala di Dante (Dante’s Hall), completely decorated with frescoes painted in the late Thirteenth Century and dedicated to Dante’s visit in San Gimignano in 1299.

Sala di Dante (Palazzo Comunale) – Photo Credit: Andrea Gigliotti

After admiring this room, your visit goes on on the second floor of the palace, where you can visit the art gallery, home to works by some prominent Sienese and Florentine artists. The most renowned among those artists are Filippino Lippi and Pinturicchio.

Once you have concluded the visit in the art gallery, it’s time to head towards the most challenging ascent of the day—the Torre Grossa (Big Tower). Most of the towers and bell towers have narrow staircases that make the climb quite tough. However, this is not the case. The stair isn’t too small, and you can go up smoothly while other tourists come down. The trickiest part is the last flight (ten steps more or less), which leads outside on top of the tower. Anyway, you’ll be amply compensated by the beautiful view over San Gimignano and the surrounding hills (Val d’Elsa).

San Gimignano dalla Torre Grossa – Photo Credit: Andrea Gigliotti
Duomo di San Gimignano – Photo Credit: Andrea Gigliotti

The last attraction in this plaza is the Duomo (Dome), built around the year 1000. The interior is entirely decorated with frescoes painted in the XIV Century and depicting the life of San Cristoforo (counterfacade), stories from the New Testament (right nave) and the Old Testament (left nave). Before leaving the church, you can’t miss a stop at the Chapel of Santa Fina, the dearest saint for the inhabitants of San Gimignano.

Not far from Piazza del Duomo, you can walk around Piazza della Cisterna (Plaza of the Tank). Its name is due to the tank used in the Middle Ages to collect water.

Piazza della Cisterna – Photo Credit: Andrea Gigliotti
Chiesa di San Lorenzo in Ponte – Photo Credit: Andrea Gigliotti

With a slight detour in Via Castello, you can visit the Church of San Lorenzo in Ponte. Inside there are several Etruscan vases and the fresco of Madonna and Child, unfortunately, the only one that arrived at us intact.

Going back to Piazza della Cisterna, you can walk beneath the archway surmounted by the Becci Tower and turn left to reach Via degli Innocenti. This is probably the most beautiful panoramic street in San Gimignano. In fact, one side of the road overlooks the hills, and the view is second only to the one you can see from the Torre Grossa.

After spending some time admiring the view, you can now go back to Via San Matteo, that soon becomes Via San Giovanni. Your tour of San Gimignano is almost over. At the end of Via San Giovanni, you’ll see Porta San Giovanni, the access (from our point of view the exit) of the extended city wall built to protect the hamlet.

Via San Giovanni – Photo Credit: Andrea Gigliotti

Now that you have seen the main attractions, you can go back to the highest part of San Gimignano. Instead of retracing the same road, you can zigzag among the secondary streets, less crowded but equally enjoyable.

For dinner, you will be spoilt for choices. San Gimignano offers many delicious alternatives and some typical products you can’t miss. One example is the saffron, widely used in many recipes, and the Vernaccia, the white wine typical of San Gimignano. 
We decided to have dinner at the Osteria delle Catene, in the highest part of town and near Palazzo Mari, the facility where we spent the night. This restaurant offers local dishes of the Tuscan cuisine at reasonable prices, something not so common in a city so crowded by tourists.

Our tour of Certaldo Alta and San Gimignano is now concluded. Don’t miss our next destination—the tour of Chianti.

See you!