The Middle Ages were a very fruitful and yet unstable period for Tuscany. Hilltops towns, usually used for defensive purposes littered the countryside.

The entrance to the Fosdinovo Malaspina Castle
The Malaspina Castle is the epitome of the Middle Ages fortress

Still today, visitors can glimpse at this interesting period of history by visiting some of the most well maintained medieval towns. Here is a shortlist of 5 towns spread out across Tuscany.



Barga is about 1.50 hour from Florence. It is nestled on the Garfagnana mountains in the Lucca province. 

This small town has a long standing history. Rich in natural resources, it was fought over by the bigger towns of Pisa and Lucca in the Middle Ages. Sick of suffering constant attacks from these neighbouring towns, Barga chose to ask for the protection and patronage of Florence. Over the centuries, Barga had good trade relations with the Tuscan capital. The numerous ornate Renaissance buildings attest to the past wealth of the town.

Barga seen from the distance
Barga seen from the distance

Starting from 1927, Barga suffered a slow economic decline. A great number of inhabitants immigrated to the United Kingdom or the US but by the end of the 20th century many returned and injected their savings back into their hometown. Barga is now considered the most scottish town in Italy since about 40 percent of the population has some form of Scottish connection.

What to see in Barga:

Barga’s cathedral was built over 6 centuries,  from the 11th to the 16th, and is one of the best examples of the Romanesque style in Italy. The simple lines of the white marble cathedral and its castle-like bell tower are elegant and well balanced. The inside, with its unadorned stone arches, is more austere. At the foot of the church, a stone tiled square, is the best place to admire the amazing views of the surrounding hills and the rest of the town.

Red english phone cabin in Barga
The red phone boxes are a reminder of the connection between Barga and the UK. 

Just below the cathedral and behind the Palazzo del Podesta’ is a green area with trees. This small park is called Arringo and was used throughout history as a meeting point for the inhabitants to discuss town affairs.

It is another perfect place to view the landscape.

Barga is also a great starting point for nature lovers. The hills and mountains around town are perfect for walks, horse and bike rides.

When is the best time to visit:

During the summer months the town organises many sagre. If your feeling a bit homesick, don’t miss the fish and chips (pesce e patate) food festival at the beginning of August.

Music lovers shouldn’t miss the famous Barga Jazz Festival held during most of August. Take a stroll around town and be surprised by live performances. A lot of concerts are free and others range from 5 to 15 €.



Montefioralle is immersed in the Chianti area, famous the world over for its wine. The little hamlet is less than an hour from Florence, right off the Chiantigiana road. It is surrounded by nature on all sides: vineyards, olive groves and fields. 

Montefioralle seen from distance
Think about being a Medieval pilgrim approaching Montefioralle for a place to spend the night

The town still maintains its medieval circular protective walls. Its stone houses are huddled side by side following the same ring pattern and all facing outward as if they were welcoming a visitor.

A narrow Medieval street in Montefioralle
The narrow Medieval streets would definitely be a problem for cars today

Montefioralle gives the impression that time has come to a standstill. If it weren’t for the few visible cars, one could definitely imagine oneself back in the Middle Ages.

What to see in Montefioralle:

If you feel like enjoying the Tuscan countryside, why not take a 30 min walk to the Pieve di San Cresci? This small church dates back to the beginning of the 12th century. It’s beautiful facade, with its arched windows and door, combines white stones with contrasting brick.

The inside of the windowless church is dark and womb-like. It is a good example of the baroque style. The ceiling and walls are decorated with geometric shapes.

When to go:

Wine enthusiasts should come to Montefioralle in mid-May for I Vini del Castello. This event is the perfect opportunity to sample local Chianti wine in an incredible location.



Certaldo is just 50 km to the South of Florence. 

The town is divided in two: Certaldo Alto, the old Medieval part of town, and Certaldo Basso, the more recent part that started being developed at the end of 18th century.

The Certaldo townhouse made out of brick
The brick facade of the Certaldo townhall

You can reach the Old Town by car but there are many traffic restrictions for non residents. Leave you car near Piazza Boccaccio in the lower part of town and take the funicular up the hill instead.

Certaldo’s high position and its proximity to the Francigena road made it a strategic place for a fortified town. The central tower allowed the inhabitants of Certaldo to keep an eye on the Francigena, the main access road from the north of Europe to Rome.

What started as a watchtower, quickly became a castle and then a fortified town.

All the buildings in Certaldo are made with red bricks which gives a unified and warm feel to the whole town. There is very little traffic which makes it a perfect place to stroll around and imagine how Certaldo used to be in the Middle Ages.

What to see in Certaldo:

If you want to know more about the ancient history of the town, the ground floor of the Palazzo Pretorio has a collection of artifacts found in the area around Certaldo that date back to Etruscan and Roman times. The buildings facade is covered in the crests of the important families of Certaldo.

There are three museums in Certaldo: Palazzo Pretorio, the museum of Sacred Art and Boccaccio’s house. You can buy tickets for two or three of the exhibits. The most interesting one is the Sacred Art museum in the Agostiniani Convent.

There is a beautiful Romanesque cloister to discover inside.

When to go:

If you want to discover Certaldo under a new light, visit in mid-July during the Mercantia Street Theatre Festival. The medieval town become the backdrop to all kind of performances, from acrobats to flame throwers to more traditional theatre shows.

Two masked people running on fake horses
A performance during the Mercantia Theatre Festival. Credits.

Dine with the famous writer and playwright Boccaccio in his home town for two Saturdays in June. A cena da Messer Giovanni is a torch lit dinner in Certaldo’s streets. The menu, costumes and entertainment is strictly medieval!



Fosdinovo is the North of Tuscany, right by the Ligurian border. Though it is 2 hours away from Florence, it is worth the detour. Perched at around 900 metres in the Apuan Alps, the town is surrounded by forest on all sides. On a clear day you can even see the Tyrrhenian sea. 

The Malaspina family gradually took control of the whole town and by the 14th century it was firmly in their hands. Unlike most fortified towns it didn’t suffer too many attacks and was able to prosper.

Castello Malaspina of Fosdinovo seen from distance
Malaspina Castle in Fosdinovo is quite intimidating from below.

By 1666 it became so wealthy that the Sacred Roman Empire allowed it to mint its own currency.

The beautiful Malaspina castle is right on the edge of town. The fortress dates back to the 12th century and was the official residence of the Malaspina family.

Over the centuries, members of the family added elements to the castle making it more of a Renaissance residence on the inside than a medieval castle.

During the Second World War the fortress was bombarded by the Allies. Damaged parts of the castle were painstakingly restored until the end of the 20th century and it is now one of the most stunning castles to visit around Tuscany.

Though the town itself isn’t as architecturally rich as some other towns, its location, surrounding nature and castle make it very much worth the trip.

What to see in Fosdinovo:

You can only reach the Malaspina Castle from the Northern side of town. There is a parking lot near the Campo Sportivo (football pitches) that’s a 6 min walk to the castle. During the summer there are 5 guided tours a day. Make sure to book in advance! Upon request you can even search the castle for its infamous ghost by candlelight.

If you have ever dreamed of spending the night in a castle, this is your chance! The Malaspina castle also has a bed & breakfast. Some of the views from the bedroom windows are absolutely breathtaking.

Adventure lovers might want to check out the Parco Avventura just outside of town. Immersed in the forest, it’s the perfect place for adults and kids to climb up trees, go bungee jumping or zip lining.



Monteriggioni is about 1.10 hour from Florence and 25 min from Siena. This medieval fortified town still has a complete ring of fortification and 14 square towers, a few of which are broken. 

The stone walls are so impressive that Dante himself mentioned them in the Divina Commedia.

Monteriggioni walls from above with landscape view
This is the view from the Monteriggioni wall promenade.

Monteriggioni was a Sienese defensive outpost in the war against Florence.

Located near the Francigena road and at the top of the Monte Ala, it was well located to keep an eye on their expansionist rivals.

The circular walls, which follow the natural terrain, were built over 5 years at the beginning of the 13th century.

The town is small enough to visit in half a day but won’t disappoint you with its medieval atmosphere.

Find out more about the things to see and do in Monteriggioni.

Tuscany is more than just Renaissance

Though Florence and its surrounding area was made great during the Renaissance period, the Middle Ages were a very important historical moment for Tuscany.

The little fortified villages that still dot the Tuscan countryside today are great reminders of the instability of the time and help visitors imagine how life used to be.

They are also a nice change from the bustling streets of the more popular touristic destinations.


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