Top 9 Castles to Visit in Tuscany

Castello di Brolio is a magnificent fortress and powerful symbol of Tuscany’s wine heritage. Owned by the noble Ricasoli family since 1141, it is renowned for its pivotal contribution to the world of wine, specifically as the birthplace of the Chianti Classico blend. As you explore its enchanting grounds, you will walk through the heart of a 32-generation winemaking legacy. From its fortified walls, you can take in sweeping views of the rolling Tuscan countryside, a landscape shaped by centuries of history, conflict, and viticulture.

What to Expect

Immerse yourself in a world where medieval history and world-class winemaking converge.

• Chianti Classico Tastings: Indulge in tastings of the iconic Chianti Classico, produced by the Ricasoli family winery, which continues to blend centuries-old traditions with modern techniques.
• Historic Grounds: Wander through the castle’s English-style romantic gardens, visit the Chapel of San Jacopo, and explore the Ricasoli family museum.
• Panoramic Views: Enjoy breathtaking vistas of the surrounding vineyards, olive groves, and the classic rolling hills of the Chianti countryside from the castle ramparts.
• Culinary Experiences: Pair your wine tasting with traditional Tuscan cuisine at the castle’s osteria, which offers dishes that perfectly complement the estate’s wines.
• Historical Immersion: Discover the castle's military past, evident in its robust fortifications that withstood numerous historical battles between Siena and Florence.

A Journey through History

Uncover the legacy of the "Iron Baron" and the origins of Chianti's most famous wine.

• 12th-Century Origins: The castle's history dates back to 1141, when the Ricasoli family took possession, establishing it as a key strategic outpost in the Florentine territory.
• The "Iron Baron": In the 19th century, Baron Bettino Ricasoli, a key political figure and later prime minister of Italy, developed the original formula for Chianti wine within these walls.
• Centuries of Conflict: Due to its strategic location, the castle endured numerous sieges and attacks throughout the medieval and Renaissance periods. This resulted in various architectural reconstructions.
• World War II Damage: The castle suffered significant damage from artillery fire during World War II, but was meticulously restored by the Ricasoli family thereafter.
• A Living Winery: Castello di Brolio remains the headquarters of the family's wine company, making it one of the oldest continuously operating businesses in the world and a living testament to Tuscan heritage.

Experience the soul of Chianti at its source. Let our specialists weave the history and flavors of Castello di Brolio into your personalized Culture of Tuscan Wine and Cuisine Tour.

Castello di Vincigliata is a romantic medieval castle offering stunning views of the Tuscan countryside and Florence’s iconic skyline. This fortress has magnificent crenelated towers, lush Italian gardens, and atmospheric courtyards. While now primarily a breathtaking venue for private events and weddings, a private guided tour will reveal its architectural beauty and the captivating history surrounding it. It will give you a glimpse into a past that includes noble families, visionary restorations, and wartime secrets.

What to Expect

Step into a fairy-tale setting where medieval architecture meets romantic garden design.

• Guided Architectural Tours: Explore the castle’s stunning interiors, including its loggia, courtyard, and armory, on guided tours that showcase its medieval and Renaissance features.
• Spectacular Views: Enjoy spectacular panoramic views of Florence, with Brunelleschi's Dome visible in the distance, as well as the lush hills of Fiesole.
• Lush Gardens: Wander through the beautifully landscaped gardens, filled with winding paths, fountains, and ancient trees, creating a serene and romantic atmosphere.
• Photogenic Setting: Capture incredible photographs of the castle's picturesque towers, courtyards, and terraces, which make it one of the most sought-after venues in Tuscany.
• Exclusive Atmosphere: Experience the intimate and exclusive feel of the castle, which offers a tranquil escape from the bustling city of Florence just a short drive away.

A Journey through History

Discover the story of a castle rescued from ruin and reborn as a work of art.

• Ancient Origins: The first records of the castle date to 1031, when it was owned by the prominent Visdomini family, one of Florence's oldest noble clans.
• Fall into Ruin: After changing hands multiple times between powerful Florentine families, the castle was eventually abandoned and fell into a state of complete ruin by the 17th century.
• The English Restoration: In 1855, the ruins were purchased by Sir John Temple Leader, an English nobleman who dedicated his fortune and decades of his life to meticulously restoring the castle to its former glory.
• A Prisoner-of-War Camp: During World War II, the castle served as a high-security prisoner-of-war camp for high-ranking military officers.
• A Modern Icon: Today, Castello di Vincigliata is celebrated as a masterpiece of 19th-century Neo-Gothic restoration and is a symbol of Fiesole’s rich cultural heritage.

Connect with a travel specialist to arrange a private tour of Castello di Vincigliata and other hidden gems around Florence when you embark on a Classic Tuscany Itinerary.

Castello di Verrazzano is a historic estate nestled in the heart of the Chianti Classico region. It is renowned for its ancient winemaking heritage and connection to a legendary explorer. The castle invites you to journey through centuries of history and viticulture, with guided tours of its historic halls, atmospheric aging cellars, and beautiful Renaissance gardens. Its elevated position provides beautiful views of the surrounding vineyards and olive groves. A visit here is an immersion into the story of a family and a tradition that has shaped the region for over a thousand years.

What to Expect

Savor the flavors of Chianti at the ancestral home of a great explorer.

• Historical Wine Tours: Participate in private guided tours that take you through the entire winemaking process, from the vineyards to the historic cellars, culminating in a tasting.
• Wine and Food Pairings: Indulge in tastings of exceptional Chianti Classico, Super Tuscans, and olive oil, often paired with traditional Tuscan meals served in a rustic farmhouse setting.
• Explorer's Legacy: Discover the castle’s connection to Giovanni da Verrazzano, the famed 16th-century explorer who was the first European to chart New York Harbor.
• Stunning Panoramas: Take in the magnificent views from the castle's terraces, which offer an unspoiled panorama of the Greve valley, a classic Chianti landscape.
• Wild Boar Encounters: Keep an eye out for the wild boars that roam the estate’s extensive forests and are a symbol of the Verrazzano brand.

A Journey through History

Trace the lineage of a castle from Etruscan settlement to world-renowned winery.

• Etruscan and Roman Roots: The site of the castle has been inhabited since ancient times, with evidence of Etruscan and Roman settlements found on the property.
• A Family Legacy: The Verrazzano family, whose lineage is documented back to the 7th century, has owned the estate since at least the 12th century, making it a cornerstone of local history.
• Giovanni da Verrazzano: The castle is the birthplace of the famous navigator Giovanni da Verrazzano (1485-1528), whose voyages are celebrated at the castle.
• Continuity of Winemaking: The castle's cellars hold historical records showing an uninterrupted tradition of winemaking on the estate dating back to at least 1150.
• Modern Revival: The Cappellini family acquired the castle in 1958, undertaking extensive restoration of the vineyards and the historic buildings to restore Verrazzano to its former glory as a leading Chianti producer.

Discover the heritage behind every bottle when you take our Finest Wines of Tuscany and Central Italy Tour.

Castello di Poppi is one of Tuscany’s most important and best-preserved medieval castles. Its imposing structure dominates the surrounding landscape. Exploring its beautifully preserved interiors is like stepping back in time; you can wander through grand halls, visit a chapel adorned with 14th-century frescoes attributed to Taddeo Gaddi, and browse a historical library housing over 25,000 ancient manuscripts and incunabula. The castle is a gateway to understanding Tuscany's turbulent medieval past.

What to Expect

Explore a perfectly preserved medieval fortress linked to Dante.

• Architectural Prototype: Admire the castle's design, which is believed to have served as the prototype for Florence's famed Palazzo Vecchio. It was designed by the same architect, Arnolfo di Cambio.
• The Rilliana Library: Discover the historical Biblioteca Rilliana, an impressive library containing thousands of medieval manuscripts and rare early printed books.
• Chapel Frescoes: View the stunning cycle of 14th-century frescoes in the Guidi Chapel, which depict scenes from the life of John the Baptist with remarkable color and detail.
• Panoramic Tower Views: Climb the tall central tower for breathtaking 360-degree views of the town of Poppi and the beautiful Casentino Valley.
• Battle of Campaldino Museum: Learn about the historic 1289 Battle of Campaldino through models and exhibits that detail the conflict in which the Guelphs defeated the Ghibellines.

A Journey through History

Walk in the footsteps of Dante and uncover the secrets of a pivotal medieval battle.

• The Guidi Counts: The castle was the main residence of the Counts Guidi, a powerful feudal family who ruled the Casentino region for centuries.
• Dante's Exile: The famed poet Dante Alighieri is believed to have stayed at the castle in 1310 as a guest of Count Guido da Romena, and it is said he wrote parts of his Inferno here.
• The Battle of Campaldino: The castle played a key role in the lead-up to the Battle of Campaldino, a major clash between Guelph Florence and Ghibelline Arezzo, in which Dante himself fought.
• Florentine Conquest: After the last Count Guidi was expelled in 1440, the castle fell under the control of the Republic of Florence and became the seat of its local government.
• A Symbol of Casentino: Today, Castello di Poppi is the cultural and historical heart of the Casentino region, hosting cultural events, exhibitions, and educational activities.

Uncover the medieval heart of Tuscany. Allow our experts to curate an immersive Tuscany Tour of Medieval Cities and Renaissance Preserves that includes the magnificent Castello di Poppi.

Castello di Monteriggioni is a perfectly preserved medieval fortress near Siena and one of Tuscany's most iconic and recognizable landmarks. Built by the Sienese as a defensive outpost against their Florentine rivals, the town features a complete circle of high walls and 14 imposing towers that have remained largely intact for over 800 years. As you stroll along the ancient cobblestone streets, explore quaint artisan shops, and climb sections of the ramparts for sweeping views of the surrounding Chianti countryside.

What to Expect

Walk the walls of a fortress so perfect it was immortalized by Dante.

• Intact Circuit of Walls: Walk along sections of the remarkably preserved defensive walls and imagine yourself as a medieval soldier guarding against an approaching army.
• Fourteen Towers: Admire the 14 imposing towers that punctuate the walls, creating the castle’s distinctive "crown-like" appearance when viewed from a distance.
• Medieval Festival: If you visit in July, experience the "Monteriggioni di torri si corona" medieval festival, when the town comes alive with jousts, costumed parades, crafts, and period music.
• "Monteriggioni in Arme" Museum: Explore the small but fascinating museum dedicated to medieval armor and weaponry.
• Cultural Influence: Discover the castle's influence on popular culture, from its mention in Dante's Inferno to its inspiration for settings in the Assassin's Creed video game series.

A Journey through History

Explore the story of Siena's impenetrable "crown" in the heart of Tuscany.

• Sienese Stronghold: The castle was built between 1213 and 1219 by the Republic of Siena as a frontline fortification in its long-standing conflict with Florence.
• An Unconquered Fortress: Thanks to its strategic location and formidable defenses, Monteriggioni was considered impregnable and successfully repelled numerous Florentine attacks over the centuries.
• Dante's Inferno: The castle's striking towers made such an impression that Dante Alighieri famously compared them to the circle of giants guarding the ninth circle of Hell in his Inferno.
• A Betrayal: The fortress finally fell to Florence not by force, but by betrayal in 1554, when the Sienese captain in charge simply handed the keys over to the Medici forces.
• A Living Village: Unlike many castles that became ruins, Monteriggioni has remained a small, inhabited village, preserving its authentic medieval character to this day.

Step into a living medieval legend when you customize our Perfect Private Tour of Tuscany in 2 Weeks.

Castello Malaspina is a striking medieval fortress that holds a commanding presence over the city of Massa. Its breathtaking views stretc from the marble peaks of the Apuan Alps to the blue expanse of the Ligurian Sea. Built on a rocky hill, the castle boasts an impressive and complex network of walls, towers, and courtyards. Its architecture is a fascinating blend of historical periods, reflecting its long and storied past. As you explore its grand halls and climb to the top of its towers, you can learn about the history of the powerful Malaspina family, who ruled the region for centuries and shaped its destiny.

What to Expect

Discover a fortress that bridges the mountains and the sea with its rich history.

• Layered Architecture: Observe the castle’s unique architectural evolution, from its original medieval core to the magnificent Renaissance palace built within its walls.
• Breathtaking Panoramas: Climb to the top of the castle for some of the most stunning panoramic views in Tuscany, encompassing the city, the coastline, and the dramatic Apuan Alps.
• Renaissance Palace: Wander through the sumptuously decorated rooms of the residential palace. They feature elaborate frescoes, painted ceilings, and elegant loggias.
• Defensive Structures: Explore the impressive outer fortifications, including robust bastions and defensive walls that highlight the castle’s military importance.
• Cultural Events: The castle frequently hosts art exhibitions, concerts, and cultural events, making it a vibrant center for the local community.

A Journey through History

Unravel the legacy of the powerful Malaspina dynasty in their most impressive stronghold.

• Early Medieval Origins: The first fortifications on the site date back to the early Middle Ages, likely built by the Obertenghi family, ancestors of the Malaspinas.
• The Malaspina Rule: The powerful Malaspina family took control and significantly expanded the castle from the 13th century onwards, making it the seat of their feudal power.
• From Fortress to Palace: In the 15th and 16th centuries, the castle was transformed from a purely military fortress into a refined Renaissance residence, reflecting the family's wealth and status.
• Prison and Decline: After the end of the Malaspina dynasty's rule, the castle was used as a military prison in the 19th and early 20th centuries, before falling into a state of neglect.
• Modern Restoration: The castle has been the subject of extensive restoration projects, allowing it to be opened to the public as a museum and cultural venue, preserving its unique heritage.

Experience the power and prestige of Tuscany's noble past on an Art Capitals of Italy Tour.

Castello di Meleto is surrounded by rolling vineyards in the heart of Tuscany’s Chianti Classico region. With its two imposing cylindrical towers, this fortress was once a strategic fortification in the perpetual conflicts between Florence and Siena. Today, the castle welcomes you to explore its beautifully preserved halls, a charming 18th-century theater, and ancient wine cellars. A private guided tour will provide you with fascinating insights into its history, while wine tastings and culinary experiences highlight the estate’s exceptional Chianti Classico and traditional Tuscan flavors.

What to Expect

Enjoy the perfect blend of history, wine, and Tuscan hospitality in a classic Chianti castle.

• Historical Tours: Take a guided tour to discover the castle’s furnished rooms, historical kitchens, and the enchanting Teatrino di Meleto, a tiny private theater from 1741.
• Wine and Olive Oil Tastings: Sample the estate’s acclaimed organic wines and extra-virgin olive oil in the historic wine cellars or on a panoramic terrace.
• Cooking Classes: Participate in hands-on cooking classes where you can learn to prepare traditional Tuscan dishes like the Italian fish stew, Cacciucco.
• Vineyard Exploration: Wander through the surrounding 400 acres of vineyards and olive groves that make up the castle's thriving agricultural estate.

A Journey through History

Explore a castle that stood on the front lines of the Florentine-Sienese wars.

• Benedictine Origins: The castle's history begins in the 11th century as a property of the nearby Benedictine monks of the Coltibuono Abbey.
• Strategic Stronghold: Due to its location on the border between the territories of Florence and Siena, Meleto became a key military outpost for the Florentine Republic.
• The Ricasoli Family: The castle later came into the possession of the Ricasoli family and they were responsible for many of its fortifications.
• Sieges and Fortifications: The castle endured several sieges, leading to the addition of its two massive, round Aragonese-style towers in the 15th century to defend against new cannon warfare.
• A Peaceful Transformation: After the wars between Florence and Siena ended in the 16th century, the castle was gradually transformed into a peaceful countryside villa, which is the role it enjoys today.

Indulge in the rich flavors and history of the Chianti region. Let us arrange an exclusive wine tasting and tour at Castello di Meleto as part of your In-Depth Tour of Tuscan Gourmet Cuisine.

Castello di Vicchiomaggio is a Renaissance-era castle surrounded by lush vineyards and olive groves, sitting majestically atop a hill in Greve in Chianti. Known for its rich history and exceptional wines, it showcases historic grounds, ancient wine cellars, and picturesque Italian gardens. You can indulge in wine tastings featuring its acclaimed Chianti Classico and other premium vintages while taking in breathtaking views of the Tuscan countryside from its panoramic terrace.

What to Expect

Walk in the footsteps of da Vinci at this elegant Renaissance wine estate.

• Acclaimed Wine Tastings: Enjoy tastings of the castle's award-winning wines, which are consistently ranked among the best in the Chianti Classico region.
• Renaissance Architecture: Admire the castle's beautiful Renaissance structure, including its imposing central tower, elegant courtyard, and historic defensive walls.
• Gourmet Dining: Dine at the castle’s gourmet restaurant, which serves exquisite traditional Tuscan cuisine prepared with a modern twist, perfectly paired with the estate's wines.
• Panoramic Views: From its elevated position, the castle offers some of the most spectacular and far-reaching views across the Greve valley.

A Journey through History

Uncover the castle's connections to some of the Renaissance's greatest names.

• Lombard Origins: The castle's name derives from "Vico-locus-maggiori," meaning "major village," and its origins trace back to a Lombard stronghold from around 957 AD.
• Leonardo da Vinci's Stay: The castle is famously associated with Leonardo da Vinci, who is believed to have stayed here in 1503 while painting the Mona Lisa. The landscape in the background of the painting is said to be inspired by the views from the castle.
• Literary Connections: The castle is also mentioned in historical texts by the poet Henry Wadsworth Longfellow, who wrote about its history and beauty.
• From Defense to Viticulture: Originally a defensive fortress, the castle was transformed into a Renaissance villa in the 16th century. This shifted its focus from military strategy to agriculture and winemaking.
• The Matta Family: In 1964, the castle was purchased by the Matta family, who have passionately restored it and elevated its winery to international acclaim.

Sip wine where Leonardo once sketched when you take an Art Capitals of Italy Tour.

Castello di Montegufoni is a magnificent testament to centuries of Tuscan history. Surrounded by rolling vineyards and olive groves, this medieval fortress-turned-estate offers you a serene and beautiful escape into a bygone era. You can explore its beautifully preserved architecture, including a distinctive medieval tower, rustic courtyards, and a famous gallery of masks. A visit here is an opportunity to experience the authentic atmosphere of a historic Tuscan estate while enjoying breathtaking views of the Chianti hills.

What to Expect

Discover a castle of art, history, and legend just a short drive from Florence.

• The "Room of Masks": Be captivated by the unique room decorated with whimsical and grotesque masks. It was painted in the early 20th century by the artist Gino Severini, a friend of the castle’s then-owner.
• Historic Architecture: Admire the castle’s impressive main tower, which echoes the design of Florence's Palazzo Vecchio, and wander through its numerous courtyards and loggias.
• Frescobaldi Wine: While no longer owned by the family, the castle's history is deeply intertwined with the noble Frescobaldi family, renowned for their contributions to winemaking.
• Serene Gardens: Enjoy the tranquility of the castle’s Italian-style gardens, a perfect place for a leisurely stroll and to soak in the peaceful Tuscan atmosphere.
• Proximity to Florence: The castle's convenient location makes it an ideal base for exploring the city of Florence and the surrounding Chianti countryside.

A Journey through History

Explore the rich past of a castle that once sheltered priceless Renaissance masterpieces.

• Medieval Origins: The castle dates back to the 12th century and was originally built by the Ormanni family, who were embroiled in the Guelph-Ghibelline conflicts.
• The Acciaioli Family: In the 14th century, the castle passed to the powerful Acciaioli family, who expanded it and added the imposing tower.
• Sir George Sitwell's Vision: In 1909, the castle was purchased by the eccentric English baronet Sir George Sitwell, who undertook a massive restoration and commissioned the famous "Room of Masks."
• A Wartime Sanctuary: During World War II, Castello di Montegufoni served as a secret repository for some of Florence's most priceless works of art, including Botticelli's Primavera and Uccello's Battle of San Romano, protecting them from Nazi looting and Allied bombing.

Unearth the artistic soul of the region on our Great Escape to Tuscany Tour.

Tuscany's castles are living chronicles of the region's soul. From the battle-scarred ramparts of Monteriggioni that now frame breathtaking vineyard views to the ancient cellars of Brolio where world-class Chianti is aged to perfection, each fortress tells a story of transformation.

These experiences can be thoughtfully woven into your bespoke itinerary. Whether your passion lies in private wine tastings in historic cellars, exploring artistic treasures hidden within fortified walls, or simply waking up to the serene beauty of the Chianti hills, our travel specialists can make it a reality. For more information and inspiration, see our Tuscany travel guide or Tuscany tours and travel packages.