Small Group Tour to Siena & San Gimignano with Chianti Wine

This small-group tour from Florence offers a well-rounded taste of Tuscany’s picturesque towns and renowned wines. If you’re looking for an affordable, engaging way to step into the heart of Italy’s countryside and history, this experience might be just right.

What we love about this tour is its balance: intimate small group size (up to 25 participants) ensures a relaxed, personable atmosphere, and the chance to taste authentic Chianti wines paired with regional goodies is a real highlight. Plus, visiting Siena’s stunning Piazza del Campo and the medieval towers of San Gimignano offers captivating photo opportunities and a glimpse into Italy’s architectural past.

A potential consideration is the full day’s schedule—at 10 hours, it’s quite packed, and some travelers might prefer more time in each town for wandering or shopping. But overall, this tour works best for those eager to see key highlights without the hassle of independent planning. It’s particularly suited for first-time visitors to Tuscany, wine lovers, or anyone wanting a taste of Italy’s famous medieval atmosphere with expert guidance.

Key Points

• Intimate group setting enhances personal interaction and flexibility.
• Combines cultural sightseeing with wine tasting, offering both history and flavor.
• Efficiently organized with a well-balanced itinerary covering Siena, San Gimignano, and Chianti.
• Includes local guides and expert-led wine tasting, adding depth to the experience.
• Travel in comfort with air-conditioned transport and free Wi-Fi.
• Good value for a full-day tour at roughly $142, including transportation, guides, and tastings.

You can check availability for your dates here:

The Itinerary in Detail

Starting Point and Transportation

The tour begins at the Tours & News KiosK at Piazzale Montelungo Bus Terminal, conveniently located within walking distance from Florence’s Santa Maria Novella Train Station. The use of a comfortable, air-conditioned minibus with free Wi-Fi ensures that the journey is relaxed and connected, which is a thoughtful touch. The group size caps at 25, making the experience intimate enough for questions or spontaneous stops.

Morning: Siena’s Medieval Magic

Once on the road, the first highlight is Siena, often overshadowed by Florence but equally deserving of attention. The local guide takes you through winding medieval streets filled with history. You’ll get a one-hour guided tour, during which you’ll see the famous Piazza del Campo, recognized worldwide for its shell shape and the vibrant Palio horse race held twice a year.

We loved the way Siena’s Gothic architecture is on full display, especially the Siena Cathedral, with its elaborate marble façade (though you’ll admire it from outside). The guide’s insights help bring this city’s past to life, making it more than just a pretty square.

Midday: San Gimignano’s Towers and Tapestry

After Siena, a scenic drive takes you to San Gimignano, often called the “Medieval Manhattan” for its 14 iconic towers that dominate the skyline. Walking through Piazza della Cisterna and Piazza del Duomo, you’ll sense the town’s storied past as a thriving medieval trading hub.

San Gimignano’s well-preserved medieval architecture and breathtaking panoramic views of the surrounding vineyards and olive groves are what make it a favorite for visitors. Many past travelers comment on the scenic beauty and authentic charm of the town, with one noting, “It’s like stepping into a fairytale. The towers are more impressive than I imagined.”

You’ll have free time here to explore artisan shops, pick up a souvenir, or simply soak in the atmosphere. This portion of the tour offers a perfect balance—structure with free time to wander.

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Afternoon: Chianti Wine Tasting

The final leg of the day leads you into the Chianti region, famous for its world-class wines. Here, a rustic winery welcomes you for a guided tasting session. You’ll sample the Chianti Classico and other local varieties, paired with regional specialties like pecorino cheese, cured meats, and bruschetta.

What makes this part stand out is the opportunity to learn about the winemaking process from vineyard to bottle, gaining insight into what makes Chianti wines so distinctive. Past reviews praise the generosity and knowledge of the hosts, with one saying, “The wine tasting was relaxed but informative, and the cheeses complemented the wines beautifully.”

Return to Florence

After a full day exploring history, scenery, and flavors, the return trip offers a chance to unwind and reflect on your experience. The tour ends back at the original meeting point, making logistics straightforward.

The Practical Aspects: What You Need to Know

Price and Value: At $141.61 per person, this tour offers a solid value considering the included transportation, guided tours, and wine tasting. The small-group format means more personalized attention and a relaxed atmosphere.

Duration: Lasting around 10 hours, expect an early start and a full day, but the pacing is generally comfortable. This is ideal for travelers who want to maximize their time in Tuscany without the hassle of planning individual visits.

Transportation: The air-conditioned minibus with free Wi-Fi helps keep the long drive pleasant. It’s a practical way to cover the distances between towns without fatigue.

Guides and Commentary: Having a professional, English-speaking guide throughout adds depth and context, especially at Siena and the wine estate. Past travelers highlight the guides’ friendliness and knowledge.

Included and Not Included: While transportation, guided tours, and tastings are covered, meals are not, so plan to bring snacks or budget for lunch independently. The meeting point is central, and the end point is the same, simplifying logistics.

Accessibility and Restrictions: The tour isn’t suitable for children under 3, those with back problems, or wheelchair users, mainly because of the walking involved.

Why This Tour Works Well for Travelers

This experience is perfect for those who want a well-organized day filled with iconic sights, culture, and authentic flavors. It’s especially suited for first-time visitors to Tuscany who prefer not to drive or worry about logistics, and for wine enthusiasts eager to sample regional specialties in a traditional setting.

Though it’s a long day, the mix of sightseeing, walking, and tasting keeps things lively. It offers a balanced introduction to Tuscany’s medieval charm, scenic landscapes, and celebrated wines—all in one affordable package.

The Sum Up

For travelers seeking an approachable, comprehensive taste of Tuscany, this small-group tour hits the sweet spot. It combines cultural highlights—like Siena’s beautiful Piazza del Campo and San Gimignano’s towers—with a delicious tasting of Chianti wines and regional products. The limited group size fosters a friendly, relaxed atmosphere, making it easier to connect and ask questions.

While the day is full, it’s designed to give you valuable insights without feeling rushed, perfect for those eager to see key sights and indulge in regional flavors. The scenic drives, authentic towns, and wine experience make this tour a memorable snapshot of Tuscany’s charm—ideal for first-timers or those short on time but hungry for a genuine taste of Italy.

FAQ

What is the starting point for this tour?
The tour begins at the Tours & News KiosK at Piazzale Montelungo Bus Terminal, within walking distance from Florence’s Santa Maria Novella Train Station.

How long is the tour?
The activity lasts approximately 10 hours, including travel time, sightseeing, and tasting sessions. Check availability for specific start times.

Is transportation provided?
Yes, you’ll travel in an air-conditioned minibus or minivan with free Wi-Fi, making the journey comfortable and connected.

What is included in the price?
The tour includes roundtrip transportation, professional English-speaking guides, guided tour in Siena, free time in San Gimignano, and a wine tasting at a local winery with regional products.

Are meals included?
No, meals are not included, so you should plan to bring snacks or buy lunch during free time.

Is this tour suitable for children or disabled travelers?
It’s not suitable for children under 3, people with back problems, or wheelchair users, due to walking and accessibility considerations.

Can I cancel the tour?
Yes, you can cancel up to 24 hours in advance for a full refund.

Do I need to bring anything?
Bring comfortable shoes, a hat, camera, sunscreen, and a water bottle. Pack light, as backpacks are not allowed.

Is it possible to reserve and pay later?
Yes, you can reserve now and pay later, keeping your plans flexible without upfront costs.

This tour offers an inviting way to glimpse Tuscany’s medieval past, enjoy breathtaking views, and taste its famous wines—all in a day carefully curated to maximize your experience. Whether you’re a history buff, a wine lover, or simply eager to see Italy’s iconic towns, this trip is a solid choice.

You can check availability for your dates here: