11 Spectacular Sites in Tuscany

Written by Rem Malloy, since 1995 Rem has been guiding and designing trips to Italy and all of Western Europe and is considered an expert in his field for over 30 years.

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 is a region of Italy that is renowned for its beauty, from the Renaissance capital of Florence to the area’s medieval villas and spectacularly untouched natural landscape. Along with the variety of ancient churches, palaces and bridges, there are also a number of castles dotted across the Tuscan countryside ranging from an 11th-century fortress to recently restored wine estates. You’ll feel like you’ve stepped into a fairytale!

History, art, and architecture lovers will be captivated while exploring Tuscan castles, highlighted with museums, preserved frescos and artworks, and guided tours available in many locations. Several Tuscan castles can also be rented as overnight accommodations, offering a unique travel experience and the chance to properly experience life in a medieval or Renaissance property.

Whether you’re looking for sightseeing spots, exquisite winery experiences or unique accommodations, here’s a guide to some of the best castles in Tuscany that are not to be missed on your next Italian holiday.


Castello de Boccale is one of Tuscany’s most dramatic castles, built on a coastal cliff close to the town of Livorno. It was originally a watchtower built by Tuscany’s influential Medici family in the 16th century, designed to protect the region from Saracen pirates that frequently tried to invade the area.

The interior of Boccale Castle is no longer open to the public, as it has been converted into residential apartments. However, it is definitely a site that is still worth visiting to admire the ancient exterior and beautiful surrounding coastal views. At sunrise or sunset, the red-tinged rock seems to glow in the golden light. There are also several small bathing pools created naturally by the erosion of the landscape, and Livorno itself is a lovely place to spend the day exploring.


Found in Tuscany’s Chianti wine region, the Castle of Brolio is surrounded by vineyards and farmland that produce famous wine and olive oil year-round. It has belonged to the noble Ricasoli family since it was built in 1141, and has been home to numerous generations, many of whom have contributed to the legacy of Chianti wine. 

Castello di Brolio has seen a lot of wear and tear over the years after being involved in many different battles and sieges across the centuries. Because of this, it has been rebuilt and fortified many times, so you will see numerous examples of architecture from across the ages in the castle’s design, including Romanesque and Neo-gothic additions. 

Despite being privately owned, you can visit every part of the estate except for the Baron’s personal building. Beyond touring the castle and admiring the view from the ramparts, you can also take a trip around the winery and vineyards or visit the connected restaurant. 


Poppi Castle is also known as the Castle of Conti Guidi, owned by the Guido family, which controlled the surrounding area for over 300 years between the 12th and 15th century. It’s one of the most beautiful castles in Tuscany because of its location on top of a hill that offers incredible views of the Casentino area.

Those who have already visited the Palazzo Vecchio in Florence might recognize the design of the tower that is attached to Poppi Castle. It was used by architect Arnolfo di Cambio as a prototype design before he went on to build the palace in the Renaissance city. You can take part in a tour of the castle for a small fee, or just enjoy admiring its exterior and the surrounding scenery.

There is also a fascinating legend attached to the tower that tells the story of a sister of the Guido family, who would imprison her lovers in the tower and was eventually locked in there herself by the local people who demanded justice for the men who had been taken.


Castello di Sammezzano is one of the more unique castles that you will find when touring Tuscany, thanks to its eclectic mix of architectural styles that are owed to its varied history of owners. The person who had the most influence over the interior and exterior design of the castle was Italian politician Ferdinando Panciatichi Ximenes D’Aragona, who took ownership of the building and its estate in the middle of the 19th century. 

D’Aragona redesigned the castle in the popular ‘oriental’ style that was sweeping Europe at the time, with an eastern-influenced exterior and sumptuous rooms filled with bright colours, plants and unique furniture. There were once plans to open the building as a hotel, but it is currently closed to the public as the local community campaigns to open it again as an attraction. We still thought it worthy of our list however, thanks to its architectural style and vibrant history. 


Banfi Castle is one of the most famous castles in Italy, with grounds hosting vineyards, a winery, restaurants and a hotel that make it a very popular place to visit. It’s a picturesque spot that is frequently used as a wedding venue, with incredible views of the sprawling Tuscan hills and Orcia valley everywhere you look.

Castello Banfi itself was restored in the 17th century and built on the remains of a previous castle, and after being purchased by the Italian-American Mariani family in the late 20th century it was restored and expanded in its original Renaissance style. It’s an ideal destination for those who want to spend some or all of their Italian holiday at a castle hotel in Tuscany, but it’s also a beautiful place for a day trip. 


The first mention of the Castello di Vincigliata is traced back to the year 1031, but this original fortress was almost entirely destroyed after years of being sold and inhabited by various noble families from Florence. It wasn’t until the 19th century when Lord John Temple Leader, a noble Englishman, decided to buy and restore the castle after hearing about its history and visiting the ruins. 

One of the things that stuck Lord John the most about the castle was the legend of Donna Bianca; a young girl who fell in love with and was destined to marry the son of a rival family. Though the wedding was said to have mended the family feud, on the morning of the event Biana stood at the top of the tower to watch her groom approach and saw him murdered by his brother, who refused to let the feud be forgotten. Bianca was said to have died of a broken heart right then and there, and the legend states that her ghost still haunts the castle now.

Lord John used the finest architects, painters, sculptors and decorators to restore the Castle of Vincigliata in a medieval style. It is now open to the public and frequently used as a venue for weddings and other grand events.


Malaspina Castle is one of the best-preserved medieval castles in Tuscany, standing on a hill overlooking the town of Massa and Italy’s coast. Its original structure was built on and expanded in a Renaissance style by the Malaspina family who ruled the area in the 14th and 15th century. 

After many centuries as a family estate, the castle was then turned into a prison in the 19th century and used as such until the end of World War Two. It is now a privately owned building that houses a museum detailing the castle’s history, a bed and breakfast and a cultural centre that accommodates artists and writers.


The Castle of Montalto is actually a medieval hamlet housed inside castle walls, situated in the hills near to Siena in Tuscany. It is thought to have first been constructed over 1000 years ago and suffered damage from many different battles and sieges that took place between Sienese and Florentine forces.

In the middle of the 1500s, Castello di Montalto fell under the rule of the famous Medici family as all of Tuscany succumbed to Florentine power. After this, many Renaissance features were added to the castle’s architecture and the surrounding land was turned into a farm that is still run by the inhabitants of the area today. 

The main castle building is now owned by the Coda-Nunziante family, who have converted some of the other buildings inside the walls into holiday properties. From the area, you can explore other nearby ancient settlements such as Montepulciano or Montalcino, or just enjoy the hospitality of the estate and its organic farm. 


Castello Vicchiomaggio is a location steeped in history, originally built in the 1400s around a stone tower that is thought to have been constructed in the 12th century. Much of the castle’s architecture is Renaissance so it is certainly not as medieval as many of Tuscany’s castles, but is still a very beautiful place that you can visit and also stay in, thanks to its status as a hotel.   

Vicchiomaggio Castle’s most exciting historical role was during the conflict between Florence and Siena, where its position in the countryside between the two cities made it a vital part of Florence’s protection. The great artist Leonardo da Vinci also stayed at the castle during the period that he painted his masterpiece the Mona Lisa, which is proven by a drawing of the castle that has been preserved within the collection of his personal documents.


Castello di Montegufoni is in a picturesque part of the Tuscan countryside, with a varied history that stretched right back to the 10/11th century when it was first built. Montegufoni Castle has had many owners and many periods of refurbishment after sustaining damage, and was also used to house some of Florence’s most valuable pieces of art during the Second World War.

Art fans will be delighted by ‘The Room of Masks’ inside the castle, which is decorated with frescoes by Gino Severini. In the 20th century, the building was converted into flats and is now one of the most popular castles to stay in Italy as a holiday destination. 


The Castle of Porciano sits in Tuscany’s Casentino Valley overlooking the town of Stia, and is another ancient building that was once owned by the noble and powerful Guido family. It has a huge iconic tower that is far larger than the rest of the castle and was constructed in the 13th century.

Castello di Porciano holds the claim to fame that the incredibly famous writer Dante Alighieri was a guest at the castle whilst he was exiled from Florence during the 14th century. Here he wrote three of his most famous epistles; “To the princes and people of Italy”, “To the Florentines” and “To Henry VII”.

Since the 1960s the castle has been privately owned, and the top three floors of the building are the home of the family who restored it to its former glory. The bottom three floors are open to the public and feature many interesting artefacts and stories relating to the Castle of Porciano and the surrounding area. 

If this guide to some of the best castles in Tuscany has made you keen to explore this stunning region of Italy, get in touch with our experts at Italy4Real and find out more about our incredible Italian trips and tours.

About the Author

Rem Malloy started Italy4real back in 1995 with his mother, Deborah de Maio.

He specialises in Italian tours as well as customised tours to France, England, Ireland, Germany, Switzerland, Greece and Spain. He was also featured in the Travel Channel show Mysteries at The Museum in 2016.

Rem has family in Italy and his mothers home town is Cava di Terrani, near the Amalfi Coast. The family has a street named after them in Sorrento, Via Luigi de Maio; a relative who was mayor of Sorrento.

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