Chianti and San Gimignano Tour: Wine, Towers, and a Taste of Tuscany

Overview

Embark on a journey through the soul of Tuscany with this exclusive wine and gourmet experience. Enjoy a wine tasting at a renowned vineyard in Chianti, a region celebrated for its prestigious wines and rolling countryside. Then head to the medieval town of San Gimignano, famed for its iconic towers, Renaissance frescoes and artisan traditions. Along the way we'll delve into Tuscany’s culinary heritage, savoring local dishes at a lunch amongst the vines. With private transportation included, this is the best way to visit this enchanting part of Italy!

Description

Get to Grips with Chianti, Tuscany’s Most Iconic Wine

 

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. Learn about the unique terroir, the aging process in oak barrels, and what distinguishes a Chianti Classico from a Riserva. Then comes the tasting itself: sample a curated selection of wines, including Chianti Classico and Chianti Riserva, and discover the meticulous techniques that give each wine its distinctive character. You’ll leave with a deeper appreciation for what makes Chianti one of the most celebrated wine regions in the world.

 

Explore Stunning San Gimignano

 

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. 

You’ll have ample free time to visit the highlights of the town at your own pace and according to your own interests: you will certainly want to stop at 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, where Benozzo Gozzoli’s paintings are some of the greatest works of the early Renaissance. 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.

 

Duomo of San Gimignano

 

Don’t be fooled by the modest Romanesque facade of the town’s Duomo - inside splendor awaits, with breathtaking frescoes adorning almost every surface. 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. 

 

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.

 

Treat Yourself with an award-winning gelato

 

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.

 

Lunch Among the Vines: A True Tuscan Feast

 

After working up an appetite exploring San Gimignano we’ll continue to one of San Gimignano’s most esteemed wineries, where an elegant lunch awaits. Set within a panoramic vineyard estate, your three-course meal showcases the very best of Tuscan cuisine, prepared with seasonal, local ingredients - all paired with expertly selected estate wines.

Whether you're a seasoned oenophile or simply love good food, this is the perfect way to end your day in one of Tuscany’s most fabulous regions - with mouthwatering dishes, fine wines, great company and an unmatched view. See you there!