Exclusive Siena and San Gimignano Tour & Chianti Wine Experience

The Exclusive Siena and San Gimignano Tour & Chianti Wine Experience offers a well-rounded journey through some of Tuscany’s most iconic sights, all within a 10.5-hour day. For $122.44 per person, participants are transported in a comfortable, air-conditioned GT coach to explore Siena’s medieval charm, indulge in a Chianti wine tasting at a traditional winery, and wander the well-preserved streets of San Gimignano. This tour caters to those interested in history and wine, with a small group size of up to 25 participants ensuring a more intimate experience.

While the pace can sometimes feel tight—especially with the timing of stops—overall, this tour offers a thoughtful blend of cultural sights, scenic countryside, and regional flavors. It’s an ideal option for visitors wanting a curated taste of Tuscany’s highlights in a single day, with the advantage of expert guides and included tastings.

Key Points

• Small-group tour with up to 25 people ensures a more personalized experience.
• Includes a guided 1-hour tour of Siena with a local expert guide.
• Visiting Siena’s Piazza del Campo and the Siena Cathedral—both highlights of the city.
• Wine tasting at a Chianti winery with regional products like olive oil, pecorino cheese, and cured meats.
• Time in San Gimignano with free time to explore the medieval towers and artisan shops.
• Enjoy a famous gelato from Gelateria Dondoli in San Gimignano.
• Roundtrip transportation from Florence with free Wi-Fi.
• Includes the tasting of local wines and products, but excludes the Duomo di Siena entry fee.

Siena’s Medieval Streets and Artistic Treasures

This tour begins in Siena, a city celebrated for its classic medieval atmosphere and artistic marvels. The local guide guides visitors through narrow streets that echo centuries of history. The standout highlight is the Piazza del Campo, renowned across Europe for its distinctive shell shape and lively ambiance, especially during the Palio horse race.

The Siena Cathedral is a Gothic masterpiece, decorated with marble floors and artworks by Michelangelo and Donatello. Visitors can admire it from the outside, appreciating its detailed exterior, while inside, the cathedral’s artistic richness makes a lasting impression. A visit to Piazza Salimbeni offers a more relaxed peek into Siena’s financial history, with the Palazzo Salimbeni standing as a symbol of the city’s historic prosperity.

Exploring Siena’s Historic Heart

The Duomo di Siena is not included in the ticket price but can be admired from the outside. It embodies Italian Gothic architecture and is a lasting symbol of Siena’s artistic achievements. The guide leads you through the city’s streets, sharing stories of Siena’s rivalry with Florence and its medieval significance. The roughly 3-hour visit provides enough time to appreciate Siena’s lively atmosphere and architectural beauty without feeling rushed.

Chianti Winery and Locally-Paired Tasting

A highlight of the tour is the visit to a traditional Chianti winery. The guided tasting features Chianti Classico and other regional vineyards, with a focus on winemaking traditions. Alongside the wines, guests sample olive oil, pecorino cheese, cured meats, and bruschetta, which are typical regional products.

The 2-hour winery stop offers an opportunity to learn about grapevine cultivation and wine production, making it informative even for those new to Tuscan wines. The tasting experience emphasizes passion and traditions, providing a flavorful taste of Chianti’s renowned wines.

San Gimignano’s Medieval Skyline and Artisanal Charm

After the winery, the tour moves into San Gimignano, often called the “Medieval Manhattan” for its 14 ancient towers dominating the skyline. The town’s well-preserved medieval architecture and picturesque streets make it a favorite stop. Visitors stroll through Piazza della Cisterna and Piazza del Duomo, exploring artisan shops and enjoying the spectacular views of vineyards and olive groves.

The free time in San Gimignano allows visitors to appreciate the town’s historic ambiance at their own pace. Many opt to visit Gelateria Dondoli, renowned for its award-winning gelato, a sweet treat that has garnered international acclaim. The 30-minute stop is perfect for indulging in authentic Italian gelato and soaking in the town’s medieval charm.

San Gimignano’s Key Landmarks and Panoramas

The Collegiata di Santa Maria Assunta provides a Romanesque exterior and a window into San Gimignano’s artistic and architectural heritage. While the interior is not included in the tour, the exterior alone offers insight into medieval religious architecture.

The Rocca of Montestaffoli is a historic fortress where visitors can explore both the exterior and interior, enjoying breathtaking panoramic views from its top. The fortress’s imposing structure and medieval appearance serve as a tangible link to San Gimignano’s past.

Return to Siena’s Main Square and Landmark Tower

The tour concludes with a visit to Piazza del Campo in Siena once again, where guests admire the Torre del Mangia. Built between 1338 and 1348, the tower was designed to match the height of Siena’s cathedral bell tower, symbolizing the balance between religious and civic power. The 1-hour stop offers the chance to absorb Siena’s historic atmosphere before returning to Florence.

Practical Details and Logistics

This VIP small-group tour operates with a roundtrip from Piazzale Montelungo in Florence, starting at 9:00 am. The transportation is in an air-conditioned minibus with free Wi-Fi, making the journey comfortable and connected. The tour includes an expert English-speaking guide and a tour leader to enhance your experience.

The tour is suitable for individuals with moderate physical fitness, as some walking on cobbled streets and uphill areas may be involved. The tour’s timing is generally well-structured, but some reviews note that timing could be improved, especially during busy periods.

Limitations and Considerations

While the tour offers a rundown, entry to the Siena Cathedral is not included in the ticket price. Some stops, such as the Duomo di Siena and Collegiata di Santa Maria Assunta, are viewed from the outside. Visitors should also plan for some walking and standing during the stops in San Gimignano and Siena.

This tour is best suited for those interested in history, architecture, and wine. It offers limited free time in San Gimignano, so those wanting to explore in depth might prefer longer visits. The tour’s smaller group size enhances the experience, but it’s not suitable for those seeking a fully independent exploration.

Final Thoughts on the Siena and San Gimignano Experience

This tour provides a curated glimpse into Tuscany’s most iconic towns, combining cultural highlights with regional wine tastings. The guides’ knowledge and the scenic countryside help create a well-balanced day. The inclusion of a Chianti winery visit and local product tastings adds flavor to the experience that simply sightseeing cannot match.

This experience is particularly good for travelers who appreciate history and wine within a manageable, small-group setting. While it may feel a bit rushed at times, the quality of the sights and tastings makes it a worthwhile choice for those wanting a comprehensive day trip from Florence.

Frequently Asked Questions

Is transportation included in the tour?
Yes, roundtrip transportation from Piazzale Montelungo in Florence is included, in an air-conditioned minibus with free Wi-Fi.

How long is the free time in San Gimignano?
Guests enjoy approximately 2 hours of free time to explore San Gimignano’s streets, shops, and landmarks.

Are meals included in the tour?
No, meals are not included. However, the wine tasting at the winery includes regional products such as olive oil, pecorino cheese, and cured meats.

What stops does the tour include in Siena?
Stops in Siena include Piazza del Campo, the Siena Cathedral exterior, and Piazza Salimbeni. The Duomo di Siena can be admired from the outside, but entry is not included.

Is this tour suitable for children or those with mobility issues?
The tour requires moderate physical activity and involves walking on cobbled streets and some uphill areas, so it’s best for those with moderate fitness levels.

Can I cancel or change my booking?
Yes, free cancellation is available up to 24 hours before the start time, providing flexibility if plans change.