Chianti and San Gimignano: Exclusive Wine and Arts Tour

Overview

Embark on a journey through the soul of Tuscany with this exclusive wine and gourmet experience. We explore the renowned Chianti Classico region, celebrated for its prestigious wines, rolling vineyards, and timeless charm. The tour also takes us to the medieval town of San Gimignano, famed for its iconic towers and artisan traditions. Along the way, we delve into Tuscany’s culinary heritage, savoring local dishes with exceptional wines.

Description

Your day begins with a scenic drive through Tuscany’s iconic countryside, offering breathtaking views of vine-covered hills and ancient olive groves. Arrive at a historic, family-run vineyard in the heart of the Chianti Classico region, where you’ll be introduced to the art and science of winemaking. Sample a curated selection of wines, including Chianti Classico and Chianti Riserva, and discover the meticulous techniques that give each wine its distinctive character. Next, continue to San Gimignano, famously dubbed the “Medieval Manhattan” for its towering skyline. Enter through one of its historic gates—Porta San Matteo, Porta San Giovanni, or Porta Quercecchio—and step into a world where time seems to have stood still. As you explore its medieval streets, marvel at the 13 surviving towers that once symbolized the town’s wealth and power. The town’s historic center is a treasure trove of architectural and artistic wonders. Visit Piazza del Duomo, home to significant landmarks such as the Palazzo Vecchio del Podestà, the Palazzo Comunale, and the Collegiate Church of Santa Maria Assunta, which houses exquisite frescoes by renowned Tuscan artists. The town’s perimeter is equally captivating, featuring a series of historic churches adorned with stunning frescoes, such as Sant’Agostino, San Jacopo, and San Bartolo. For panoramic views of the Tuscan landscape, don’t miss a walk up to the Rocca di Montestaffoli, a 14th-century fortress surrounded by olive groves.

 

Hidden gems of San Gimignano

 

• Piazza della Cisterna

• Ghirlandaio’s Fresco in the Chapel of Santa Fina

• Duomo di San Gimignano

• Rocca di Montestaffoli

• Church of Sant’Agostino

 

 

Piazza della Cisterna

 

A short walk from Piazza del Duomo, we move towards the picturesque Piazza della Cisterna, a triangular square named after the ancient cistern. The lively piazza was once the heart of medieval life, bustling with markets, festivals, and even jousting tournaments. Surrounded by imposing medieval towers and historic buildings, each with its own story, the square exudes an atmosphere of timeless charm. As we take in the details, Palazzo Tortoli, with its elegant 14th-century windows, and the mysterious Torre del Diavolo (Devil’s Tower), captures our imagination. According to local lore, the tower grew taller while its owner was away—an unexplained phenomenon attributed to the devil himself.

We pause to admire the square's harmony, and for those with a sweet tooth, a stop at Gelateria Dondoli is a must. Known worldwide, this award-winning gelateria offers unique flavors like saffron cream and pine nut. The climb to Piazza della Cisterna may be steep, but the reward—both in view and gelato (ice cream)—is undeniably worth it.

 

Ghirlandaio’s Fresco in the Chapel of Santa Fina

 

From Piazza della Cisterna, we head towards the Chapel of Santa Fina, nestled within the Duomo. Here, we find ourselves surrounded by the vibrant colors and profound devotion depicted in Domenico Ghirlandaio’s frescoes. The poignant story of San Gimignano’s patron saint, Fina, unfolds before us. Lying on her wooden plank, she is comforted by a vision of Saint Gregory the Great, who foretells her passage to eternal life. The frescoes vividly portray her trials and the miraculous events that followed her death: the healing of a paralyzed nurse, the restoration of sight to a blind child, and the tolling of the town’s bells by angels.

The chapel’s details invite us to linger—a hidden mouse under the plank, symbolizing the hardships she endured, adds a touch of humanity to this sacred space. As we stand in quiet reflection, the enduring legacy of Santa Fina comes alive, offering an intimate connection to the town’s spiritual heritage.

 

Duomo of San Gimignano

 

From the Chapel of Santa Fina, we walk back into the Duomo of San Gimignano, whose modest Romanesque facade belies the splendor within. Inside, we are greeted by walls adorned with breathtaking frescoes. On the left side, Bartolo di Fredi’s Old Testament stories unfold in rich detail, while the right side features the New Testament cycle attributed to Simone Martini’s followers.

Our journey through the nave reveals the dramatic Judgment Day fresco by Taddeo di Bartolo, commanding attention with its bold imagery. The transept hides more treasures, such as the Chapel of Santa Fina, where Ghirlandaio’s masterpiece continues to inspire, and the 13th-century wooden crucifix, radiating an almost mystical aura. Nearby, the Museum of Sacred Art invites us to delve deeper into Tuscany’s artistic and spiritual traditions with its collection of illuminated manuscripts, sculptures, and intricate silverwork.

 

Rocca di Montestaffoli

 

A short ascent from the Duomo brings us to the Rocca di Montestaffoli, a serene escape from the bustling town center. This 14th-century fortress, built to defend San Gimignano from neighboring Siena, offers a peaceful setting surrounded by olive groves. As we explore the remnants of the Rocca, the climb to its remaining tower rewards us with sweeping views of the Val d’Elsa and the iconic skyline.

During the Giostra dei Bastoni, a medieval reenactment held annually in June, the Rocca comes alive with vibrant color and historical pageantry. Whether resting in the shade of the olive trees or marveling at the panoramic vistas, we feel transported to a bygone era, where history and nature intertwine seamlessly.

 

Church of Sant’Agostino

 

A short stroll from the Rocca leads us to the Church of Sant’Agostino, a hidden gem often overlooked by hurried visitors. Its modest exterior belies the artistic treasures within. As we step inside, the stunning fresco cycle by Benozzo Gozzoli comes into view, illustrating the life of Saint Augustine with vibrant detail and emotional depth.

We take our time exploring the aisles, where the maiolica-tiled floor by Andrea della Robbia adds a colorful touch. The Cappella di San Bartolo, with its intricately carved altar by Benedetto da Maiano, is a testament to the devotion to its saints. This peaceful church invites us to pause and reflect, offering a moment of quiet appreciation for the artistry and spirituality that define San Gimignano’s rich heritage.