Tuscany Wine and History Exploration Tour

Board a comfortable, fully-equipped GT coach and set off to discover the wonders of Tuscany.
The first stop of this small group tour will be the magnificent city of Siena. Here, accompanied by a local guide, you’ll have the opportunity to stroll through the charming streets of the city, admiring the stunning Piazza del Campo and the impressive Siena Cathedral.

No trip to Tuscany would be complete without a stop at a Chianti winery. Take a relaxing break during your tour and indulge in a tasting of some of the region's most iconic wines. Alongside the wine, you'll also enjoy a selection of delicious local products, allowing you to savor the authentic flavors of Tuscany.

End your journey exploring San Gimignano, known for its 14 medieval towers and breathtaking views of the Tuscan countryside. Wander through its charming streets and piazzas, taking in its well-preserved architecture.

A perfect blend of history, beauty, and wine, this tour offers an unforgettable taste of Tuscany!

Meeting Point

Piazzale Montelungo

Piazzale Montelungo, Firenze FI, Italy

TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL
Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!

What's included:

• Expert English Only Tour Leader
• Free time in San Gimignano
• Roundtrip transportation by air-conditioned minibus or minivan with free wi-fi
• 1 Hour English Only Guided tour of Siena with an Expert Local Guide
• Sampling of wines, extra-virgin olive oil and regional products
• Visit of a typical Chianti Winery with wine tasting
• VIP Small Group Tour up to 25 participants

Not included:

• Pick up and drop off
• Gratuities

What to expect:

Duration: 10 hours, 30 minutes

Siena

Siena

The adventure begins in Siena, a city celebrated for its medieval charm and rich cultural heritage. A local guide will take you through its narrow streets, unveiling centuries of history. Admire the iconic Piazza del Campo, one of Europe’s most renowned squares, famous for hosting the thrilling Palio horse race. Marvel at the stunning Siena Cathedral, a Gothic masterpiece adorned with intricate details, marble floors, and priceless works of art by masters like Michelangelo and Donatello. Experience the lively atmosphere of this historic city, a proud rival of Florence throughout history.

3 hours

Piazza Salimbeni

Piazza Salimbeni, Siena, 53100

Stroll through Piazza Salimbeni and admire the stunning architecture of the buildings surrounding the square. The iconic Palazzo Salimbeni stands as a symbol of the town’s financial history, offering a glimpse into Siena’s rich past while providing a peaceful and picturesque setting in the heart of the city.

30 minutes

Duomo di Siena

Piazza del Duomo 8, , Siena, 53100

Follow your guide and admire from the outside the outstanding Duomo di Siena
The Duomo di Siena, or Siena Cathedral, is one of the most remarkable examples of Italian Gothic architecture. Dedicated to the Virgin Mary, it was constructed between the 12th and 14th centuries and stands as a symbol of Siena’s rich history and artistic legacy.

30 minutes • Admission Ticket Not Included

Strada in Chianti

Strada in Chianti

Continue your amazing journew with a visit to a traditional winery in the Chianti region, where you’ll indulge in a guided wine tasting experience. Savor the rich flavors of Chianti Classico and other local varietals, perfectly paired with regional delicacies like pecorino cheese, cured meats, and bruschetta. Learn the secrets of winemaking, from grapevine to glass, and embrace the traditions and passion that define this celebrated wine region.

2 hours

San Gimignano

San Gimignano

Next, travel through the idyllic Tuscan countryside to reach San Gimignano, a hilltop town often called the "Medieval Manhattan" for its iconic skyline of 14 ancient towers. Explore Piazza della Cisterna and Piazza del Duomo, stroll along charming streets lined with artisan shops, and admire the town’s remarkably preserved medieval architecture. The stunning views of vineyards and olive groves stretching out to the horizon will leave you spellbound, making San Gimignano an unforgettable highlight of your day.

2 hours

Piazza Della Cisterna

San Gimignano, 53037

Make your way to Piazza della Cisterna, the heart of San Gimignano’s historic center, and savor the internationally acclaimed, award-winning gelato from Gelateria Dondoli.

30 minutes

Collegiata di Santa Maria Assunta - Duomo di San Gimignano

Piazza del Duomo 2, , San Gimignano, 53037

Admire the Duomo of San Gimignano from the outside, with its impressive Romanesque facade and beautiful positioning in the heart of the town, offering a glimpse of its medieval charm and historical significance.

30 minutes • Admission Ticket Not Included

Rocca of Montestaffoli

Via della Rocca 6, San Gimignano, 53037

Explore the Rocca di Montestaffoli, both from the outside and within, where you can appreciate its imposing structure and wander through its historic interior. From the top, enjoy breathtaking panoramic views of San Gimignano and the surrounding countryside, immersing yourself in the rich medieval heritage of the town.

30 minutes

Piazza del Campo

Il Campo, , Siena, 53100

Visit one of the most significant squares in the city of Siena and let yourself be captivated by the imposing "Torre del Mangia". Built between 1338 and 1348, it was designed to match the height of the Siena Cathedral's bell tower, symbolizing the harmony between religious and civic authority in the city.

1 hour