Exploring the historic towns of Siena and San Gimignano is a must-do for any visitor to Tuscany. This small group tour offers an immersive experience, guiding you through the region’s architectural gems and introducing you to its renowned Chianti wines. With roundtrip transportation and a professional English-speaking leader, you’ll explore the area’s rich cultural heritage and savor the flavors that make Tuscany so captivating. Whether you’re a first-time traveler or a seasoned explorer, this tour promises to uncover the authentic charm of these enchanting destinations.
Key Points

- A small group tour that visits the historic towns of Siena and San Gimignano, with a Chianti wine tasting experience.
- Roundtrip transportation, a professional English-speaking guide, and ample free time to explore the destinations.
- Highlights include the Piazza del Campo in Siena, the Gothic Siena Cathedral, and the medieval towers of San Gimignano.
- Opportunity to sample renowned Chianti Classico wines and regional specialties at a traditional Chianti winery.
- Tour group size is limited for a more intimate and personalized experience.
Overview of the Tour

The small group tour to Siena and San Gimignano offers a comprehensive exploration of two picturesque Tuscan towns. Priced from $136.53 per person, the 10-hour experience includes roundtrip transportation, a professional English-speaking guide, and a wine tasting session.
Participants will visit Siena’s iconic Piazza del Campo and Duomo, as well as meander through the winding medieval streets. In San Gimignano, they’ll marvel at the town’s 14 preserved towers and browse artisan shops.
The tour provides ample free time to soak in the unique atmospheres of these historic destinations. Comfortable shoes and a camera are recommended for this small group adventure.
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Exploring Siena

As visitors step into the historic heart of Siena, they’ll encounter the city’s iconic Piazza del Campo, a stunning Renaissance square that serves as the centerpiece of this medieval gem.
Guided by their tour leader, they’ll admire the impressive Siena Cathedral, its Gothic façade adorned with intricate marble artwork.
Strolling through the winding streets, they’ll discover the city’s well-preserved architecture and learn about its rich history.
Visitors strolling through Siena’s winding streets will discover the city’s well-preserved architecture and learn about its rich history.
With the tour leader’s expertise, visitors will gain a deeper understanding of Siena’s cultural significance and its role as an important Tuscan destination.
Discovering San Gimignano

Next, the tour visits San Gimignano, known as the "Medieval Manhattan" for its well-preserved towers that dominate the skyline.
Guests will explore the charming town and marvel at the panoramic views from its hilltop location. They’ll stroll through the quaint streets lined with artisan shops, tracing the history of the 14 medieval towers that still stand tall.
The tour provides free time to wander at your own pace, allowing you to soak in the atmosphere of this UNESCO World Heritage Site and capture photos of the striking architecture and stunning vistas.
Chianti Wine Tasting Experience

After exploring the charming town of San Gimignano, the tour takes guests to a traditional Chianti winery for a wine tasting experience.
At the winery, travelers sample the renowned Chianti Classico and other local wines. The tasting is accompanied by regional specialties like pecorino cheese, cured meats, and bruschetta.
Travelers sample renowned Chianti Classico and local wines, accompanied by regional delicacies like pecorino, cured meats, and bruschetta.
Guests have the opportunity to learn about the winemaking process and the unique characteristics of Chianti wines. This immersive experience provides insights into the rich wine culture of the Tuscany region.
The wine tasting completes the day’s exploration of the area’s history, architecture, and gastronomy.
More Great Tours NearbyTransportation and Tour Leader

The tour includes roundtrip transportation by air-conditioned minibus or minivan, which provides free Wi-Fi for passengers’ convenience.
A professional English-speaking tour leader accompanies the small group, ensuring a seamless and informative experience. The group size is limited to 25 participants, creating an intimate atmosphere and allowing for personalized attention.
The tour leader’s expertise guides visitors through the highlights of Siena and San Gimignano, providing insights and historical context.
Pickup and drop-off at the designated meeting point are included, making it a hassle-free and enjoyable day trip from Florence.
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Small Group Size and Inclusions

The small group size of up to 25 participants allows for a more intimate and personalized experience during the tour. The tour includes roundtrip transportation by air-conditioned minibus/minivan with free Wi-Fi, and a professional English-speaking tour leader to guide you. Here’s what else is included:
| Inclusion | What You Get |
| — | — |
| Guided Tour | 1-hour guided tour in Siena |
| Free Time | Free time in San Gimignano |
| Wine Tasting | Wine tasting session with regional products |
| Pickup/Drop-off | Hotel pickup and drop-off |
| Small Group | Small group size (up to 25 participants) |
Meeting Point and Accessibility
According to the important information provided, the meeting point for this tour is at the Tours & News Kiosk at Piazzale Montelungo Bus Terminal, which is located 5-10 minutes from the Santa Maria Novella Train Station.
The tour isn’t suitable for children under 3, individuals with back problems, or wheelchair users. Participants should wear comfortable shoes and bring a hat, camera, sunscreen, and water. Smoking and backpacks aren’t allowed.
It’s recommended to check the weather forecast and dress appropriately to ensure a comfortable and enjoyable tour experience.
Preparation Tips

To ensure a smooth and enjoyable tour experience, participants should come prepared. Comfortable shoes are a must, as the tour involves walking through historic city centers.
A hat and sunscreen are recommended, as the tour takes place outdoors, and the Mediterranean sun can be intense. Bringing a water bottle is also advised for staying hydrated.
Participants should avoid bringing bulky backpacks, as they can be cumbersome during the tour. Plus, smoking isn’t permitted.
Before the tour, it’s a good idea to check the weather forecast and dress accordingly to make the most of the experience.
Frequently Asked Questions

What Is the Cancellation Policy for This Tour?
The tour offers free cancellation up to 24 hours in advance for a full refund. Customers can reserve the tour now and pay later, providing flexibility with their travel plans.
Do I Need to Bring Any Special Equipment for the Wine Tasting?
No special equipment is needed for the wine tasting. Guests can simply bring an appetite to enjoy the Chianti Classico and local wines paired with pecorino cheese, cured meats, and bruschetta at the traditional Chianti winery.
Is There an Option to Extend the Tour Duration?
The tour duration cannot be extended. It’s a fixed 10-hour itinerary that can’t be lengthened. Customers must adhere to the set schedule and can’t customize the tour duration based on their preferences.
Can I Request a Private Tour Instead of a Small Group?
Yes, you can request a private tour instead of a small group tour. Many tour operators offer private tour options that provide a more personalized experience, though they may have a higher price point than the small group tour.
How Do I Redeem the "Reserve Now & Pay Later" Option?
To redeem the "reserve now & pay later" option, simply select that option during the booking process. This allows you to hold your spot without making full payment until closer to the tour date.
The Sum Up
This small group tour to Siena and San Gimignano offers an immersive Tuscan experience. Travelers can explore the iconic Piazza del Campo, marvel at the Gothic Siena Cathedral, and wander through San Gimignano’s charming medieval streets. The Chianti wine tasting adds a delightful local touch, while the roundtrip transportation and professional guide ensure a seamless and memorable day. It’s an excellent way to discover the rich cultural heritage of this picturesque region.
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