Small Group Tour to Siena & San Gimignano with Chianti Wine

Planning a day to explore Tuscany’s historic towns and rolling vineyards? This small-group tour from Florence offers a well-balanced mix of medieval charm, breathtaking views, and delicious wine tastings. It’s ideal for travelers who want a more intimate experience and a chance to truly savor Italy’s countryside without the hassle of organizing transport themselves.

What makes this trip stand out? First, the guided exploration of Siena, with its iconic Piazza del Campo, is both informative and visually stunning. Second, the visit to San Gimignano—often called the “Medieval Manhattan”—gives a chance to see its famous towers and enjoy panoramic vistas. Third, the Chianti wine tasting at a rustic vineyard provides a genuine taste of local flavors paired with regional specialties. One thing to keep in mind is that meals are not included, so if you’re hungry after all that sightseeing, plan for a leisurely lunch on your own.

This tour is suitable for those wanting a well-rounded immersion into Tuscany’s culture, history, and wine, especially if you prefer traveling with a small group (up to 25 people) for a more personal experience.

Good To Know

• Intimate group size ensures personalized attention and a relaxed atmosphere.
• Expert guides provide insightful commentary on Siena, San Gimignano, and wine making.
• Historic towns are explored with ample free time to wander and absorb the atmosphere.
• Stunning vistas along the Chianti hills enhance the scenic appeal.
• Authentic wine tasting with regional products like pecorino cheese and bruschetta.
• Flexible booking options with free cancellation up to 24 hours in advance.

You can check if your dates are available here:

Exploring Tuscany in a Day: What to Expect

This tour is designed for travelers who want to maximize their time while soaking up the essence of Tuscany. From start to finish, you’ll travel comfortably in an air-conditioned minibus, with up to 25 participants, making it easier to connect and ask questions without feeling lost in a crowd.

The Journey Begins: Florence to Siena

Your day kicks off from the meeting point at the Piazzale Montelungo bus terminal, just a short walk from Florence’s Santa Maria Novella station. The friendly staff, easily spotted in their fuchsia CIAOFLORENCE jackets, will guide you onto your vehicle. Expect a comfortable ride with free Wi-Fi, perfect for catching up or planning your next stops.

Once in Siena, a professional local guide will lead you through its winding streets. Siena isn’t just picturesque—it’s packed with history, from the Gothic cathedral to the famous Piazza del Campo, where the Palio horse race takes place twice a year. According to reviews, the guided tour in Siena lasts about an hour and offers fascinating insights that deepen your appreciation for this medieval city. The guide’s storytelling is praised for bringing Siena’s history to life, making the visit both educational and engaging.

Siena’s Highlights: Piazza del Campo and Gothic Marvels

The Piazza del Campo is a highlight for many visitors. Its shell shape and terracotta bricks create a striking setting, and it’s easy to see why it’s considered one of Europe’s most beautiful squares. Many reviews mention the vibrant atmosphere here, especially if you happen to visit during a festival or market day. The Siena Cathedral, with its intricate marble façade, leaves a lasting impression—even from the outside—offering a glimpse into the city’s artistic grandeur.

Transition to San Gimignano

After Siena, you’ll traverse the scenic Tuscan landscape—rolling hills dotted with vineyards, olive groves, and cypress trees—to reach San Gimignano. Known as the “Medieval Manhattan,” the town’s 14 historic towers dominate its skyline, providing breathtaking panoramic views that are often highlighted in reviews.

Here, you’ll have free time to wander the narrow streets, browse artisan shops, or sit down for a quick coffee. The Piazza della Cisterna and Piazza del Duomo are popular spots, where you can admire medieval architecture and perhaps spot a local artisan or two. Many travelers mention how the town’s atmosphere feels like stepping back in time, and the views from the town walls are consistently praised.

More Great Thing To Do Nearby

The Vineyard Experience in Chianti

The final part of your day takes you to a traditional wine estate in the Chianti region. This isn’t just a tasting session—it’s an opportunity to learn about Tuscany’s most famous wine, Chianti Classico, directly from those who produce it. Visitors often appreciate the rustic charm of the estate and the chance to sample local wines paired with regional delicacies like pecorino cheese, cured meats, and freshly made bruschetta.

According to reviews, the guided wine tasting is engaging and informative, with staff sharing the secrets behind winemaking—from vineyard to bottle. Many mention how the scenery around the winery adds to the experience, with views of vineyards sprawling across gentle hills—truly a picture-perfect setting.

The Logistics: Transportation, Timing, and Value

The roundtrip transportation in a climate-controlled minibus makes for a comfortable journey, especially considering the scenic driving through Tuscany’s countryside. The small group size ensures more personalized attention from your guide, which many travelers find helpful for asking questions or just feeling less like a number.

The duration of 10 hours allows for a relaxed pace—long enough to enjoy each stop without feeling rushed. The start times vary depending on availability, so checking ahead is recommended. Breakfast and lunch are not included, giving you the flexibility to choose your preferred places for a meal or snack during free time.

At a price of approximately $141.61 per person, this tour packs a lot of value. It combines cultural exploration, scenic views, and wine tasting—all curated in a way that balances guided insights with personal exploration. The inclusion of free Wi-Fi, professional guides, and visits to both Siena and San Gimignano makes it a well-rounded option for those wanting to see Tuscany without the hassle of planning every detail.

Authentic Experiences and Traveler Insights

Travelers consistently mention the stunning views as one of the most memorable aspects of this tour, especially in the Chianti region and from San Gimignano’s towers. Many note that the guide’s commentary helped them understand the significance of each town’s architecture and history, making the experience richer.

Some reviews highlight that timing in San Gimignano is just right, leaving enough room for a relaxed wander. Others appreciated the informative wine tasting, which included not just a tasting but background stories that enhanced their appreciation of Tuscan wine culture.

A few travelers mention that walking in Siena involves some uphill sections, so comfortable shoes are a must. Also, since meals aren’t included, it’s worth planning for a snack or late lunch to maximize your energy—especially if you want to linger in the towns rather than rushing through.

Final Thoughts: Is This Tour for You?

This small-group tour offers an excellent way to experience some of Tuscany’s most iconic sights and flavors in a single day, especially if you enjoy guided cultural insights paired with beautiful scenery. It’s perfect for travelers who want a comfortable, organized experience without sacrificing authenticity. The wine tasting at a traditional estate adds a tangible connection to the region’s culinary heritage, making this tour particularly appealing to wine lovers.

If you’re visiting Florence and want to venture into Tuscany’s medieval towns with ease, this trip delivers a good mix of history, scenery, and local flavor. Keep in mind that free time in San Gimignano allows for personal exploration, so bring your camera and some cash for souvenirs or a quick lunch.

Overall, it’s a solid value for a full day of sightseeing, especially given the small group size and knowledgeable guides. Just be prepared for some walking and bring along your curiosity—and maybe a little extra room in your suitcase for tasting souvenirs.

FAQ

Is transportation included? Yes, roundtrip transportation is provided in an air-conditioned minibus with free Wi-Fi.
What is the group size? The tour is limited to up to 25 participants, ensuring a more intimate experience.
Are meals included? No, meals are not included, giving you flexibility to choose your own lunch.
When does the tour start? The start time depends on availability; check ahead to see the current schedule.
How long is the tour? The entire experience lasts approximately 10 hours.
Is this tour suitable for children? It’s not recommended for children under 3 or for people with back problems or wheelchair users.
What should I bring? Comfortable shoes, a hat, camera, sunscreen, and water are advised.
Can I cancel? Yes, you can cancel up to 24 hours in advance for a full refund.
Does the tour include a guide? Yes, an English-speaking professional guide accompanies you throughout the day.
Is there free time in San Gimignano? Yes, you will have free time to explore at your own pace after the guided visit.

In essence, this tour offers a well-rounded, manageable way to see Tuscany’s historic towns, enjoy stunning views, and sample the region’s famous wines—all tailored for those who value a comfortable, engaging experience. It’s a fantastic choice for first-time visitors or anyone wanting a taste of Tuscany’s best in a single day.

You can check if your dates are available here: