Siena and San Gimignano: Small-Group Tour with Lunch from Florence

Traveling through Tuscany’s rolling hills, medieval towns, and vineyards is a dream for many, but knowing how to make the most of a day trip can be tricky. This small-group tour from Florence offers a well-rounded taste of Siena and San Gimignano, plus a delightful winery lunch. With a maximum of 25 travelers, you’ll enjoy a intimate experience packed with history, food, and stunning vistas.

What stands out for most travelers is the knowledgeable guides who bring the towns’ stories to life, and the delicious Tuscan cuisine that’s included in the price. A possible consideration is the tight schedule—while ample time is allotted for exploring, you’ll need to keep pace to see all the highlights. This tour suits those who love history, food, wine, and small-group intimacy, and who want a structured but flexible day out.

Key Points

• Small group size ensures personalized attention and fewer crowds.
• Expert guides enhance the experience with insider knowledge and humor.
• Visit iconic landmarks like Piazza del Campo and Siena Cathedral.
• Enjoy a scenic drive through Tuscany’s countryside with Wi-Fi onboard.
• Tasting and lunch at a family-owned vineyard offers authentic flavors.
• Ample free time allows for exploring San Gimignano at your own pace.

An In-Depth Look at the Tour Experience

Starting the Day: Comfort and Convenience

The tour begins at Piazzale Montelungo in Florence, an ideal central spot just near the train station. Early risers will appreciate the 8:00 am start, giving you a full day of exploring. The transportation is by luxurious, air-conditioned Mercedes minibus or similar, accommodating up to 25 travelers. Several reviews mention how comfortable and smooth the ride is, with free Wi-Fi available—perfect for sharing photos or catching up on social media as you leave the city behind.

The Drive Through Tuscany

As you leave Florence, the scenery becomes increasingly picturesque—vineyards, olive groves, and rolling hills stretch out in every direction. Travellers frequently comment on the beautiful countryside views that make the journey part of the experience. The driver, Francesco, is praised for being cautious and courteous, even stopping for families or pedestrians crossing the road, which adds a layer of safety and friendliness.

Siena: A Medieval Marvel

Once in Siena, the guided walk focuses on the medieval charm of this city, with stops at the Piazza del Campo and Siena Cathedral. One reviewer notes that the guide, Lorenzo, is extremely knowledgeable, sharing insights about the neighborhoods, the famous horse race (Palio), and local traditions. You’ll love seeing the distinctive black-and-white striped Siena Cathedral, though note that entry costs extra (€15) and isn’t available on Sundays or during celebrations.

The group gets to stroll through the narrow streets, admire the well-preserved architecture, and soak in the lively atmosphere of this historic city. Some travelers mention that the guided tour inside Siena’s highlights is very informative, with one reviewer emphasizing Lorenzo’s humor and local stories that make the history come alive.

Optional Siena Cathedral Tour

If you’re interested in visiting the Siena Cathedral interior, you can pay the guide €15 for the tour, but keep in mind that it’s not available on Sundays. Many find it worthwhile since the cathedral is considered one of Italy’s most beautiful churches, with intricate mosaics, stunning artwork, and a breathtaking façade.

The Vineyard and Lunch at Agriturismo Tenuta di Mensanello

After exploring Siena, the tour takes you to a family-owned Tuscan winery, the highlight of many reviews. Here, you’ll see the cellars and olive oil presses, and settle into a relaxed setting for a delicious Tuscan lunch. The meal features seasonal delicacies paired with local wines, including their well-regarded red wines, which guests rave about.

Travelers have described this part of the tour as a “highlight,” emphasizing the authenticity of the experience. One reviewer mentions the “beautiful lunch at a boutique winery,” and notes how the food is hearty and flavorful, perfectly pairing with the wines. It’s a chance to slow down, enjoy local flavors, and learn about Tuscan winemaking from the owners or staff.

San Gimignano: The Towered Town

Following lunch, the journey continues to San Gimignano, the “Medieval Manhattan,” famous for its cluster of tall towers that create a skyline unlike any other in Italy. You’ll have about an hour and 15 minutes to wander independently, giving you freedom to explore at your own pace.

Most travelers love this time to grab a gelato—the town’s gelato shops are renowned—and to admire the main street’s shops selling local crafts and souvenirs. You might also visit the Collegiata, the main church, or just enjoy the panoramic views from a vantage point. Reviewers highlight how the free time in San Gimignano offers the perfect balance between guided sightseeing and independent wandering, making it a flexible experience.

Return to Florence

The journey back to Florence wraps up around 6:00 pm, giving you plenty of time to reflect on your day. Travelers appreciate the well-organized itinerary, with many saying that it’s a full but manageable day that offers a true taste of Tuscany’s highlights.

Transport, Timing, and Group Size

The small group size (max 25 people) ensures a more personal, engaging experience. The roundtrip transportation by comfortable minibus with Wi-Fi makes the long drive enjoyable, and the pickup location right near the train station makes this tour accessible if you’re already based in Florence.

The duration of approximately 10 hours means you’ll spend a good chunk of the day immersed in Tuscan towns, but the schedule is tight enough to prevent boredom. Reviews often mention how the timing feels just right—ample exploration time balanced with guided tours and a leisurely lunch.

Pricing & Value

The cost of $171.76 per person might seem steep at first glance, but when you consider private transportation, guided tours, the lunch, and wine tastings, it becomes clear that the price reflects a comprehensive experience. Past guests frequently mention the quality of guides, the delicious food, and the scenic drives as making it a worthwhile investment.

This tour is especially good for travelers who value authentic local food, small-group intimacy, and insider knowledge—it offers a curated experience that’s more personal than larger bus tours.

Authentic Experiences and Insights from Reviews

Many reviewers mention their guides by name, like Lorenzo, Susie, and Alex, praising their knowledge, humor, and attentiveness. One traveler states, “Lorenzo was very kind and his information very interesting,” highlighting how guides bring stories and humor that elevate the experience.

The winery lunch is often described as a “highlight,” with guests enjoying the seasonal Tuscan cuisine and excellent wines. The scenery, charming towns, and local interaction all combine to make it feel like a true taste of Tuscany, not just a touristy ride.

Practical Tips for Travelers

• Book in advance—this tour is popular, often booked 73 days ahead.
• Remember to bring comfortable shoes for walking in Siena and San Gimignano’s cobblestone streets.
• If you’re interested in visiting Siena Cathedral, plan to pay €15 directly to the guide (not available on Sundays).
• For those with mobility issues, note that the tour involves some walking on uneven surfaces, and a private tour might be a better option.
• Luggage storage is available on the bus if needed, handy if you’re arriving from or heading to other destinations afterward.
• The return is around 6 pm, so consider your evening plans accordingly.

This experience is ideal for history buffs who want meaningful guided insights into Siena and San Gimignano, food and wine lovers eager to sample authentic Tuscan flavors, and travelers who prefer small-group settings over large, crowded buses. It’s perfect if you value comfort, authenticity, and flexibility—and if you’re happy to keep a lively pace for a full day of sightseeing.

It’s less suited for those seeking a very leisurely, unstructured day or travelers with mobility challenges, given the walking involved and the structured schedule.

Is hotel pickup available for this tour?
No, the tour starts at Piazzale Montelungo in Florence, near the train station.

What is included in the price?
Roundtrip transportation, guided walking tours of Siena, a winery lunch with wine tasting, and free time in San Gimignano are included.

Can I visit Siena Cathedral?
Yes, entrance to Siena Cathedral can be purchased (€15), but it’s not included in the tour price and not available on Sundays.

How long is the drive from Florence to Siena?
The scenic drive takes approximately 1 hour, with comfortable, Wi-Fi-equipped transport.

What if I want to explore Siena more extensively?
Your guide provides a structured overview, but you’re free to explore on your own during the free time, especially in San Gimignano.

Is this tour suitable for children or people with limited mobility?
It’s best suited for travelers comfortable with walking and standing; limited mobility may find it challenging.

How much time do we spend in San Gimignano?
You’ll have around an hour and 15 minutes for independent exploration, including gelato, shopping, or visiting the church.

What is the group size?
A maximum of 25 travelers ensures a more intimate experience.

Can I cancel if my plans change?
Yes, with free cancellation up to 24 hours before the tour’s start, you can get a full refund.

This tour offers a fantastic way to experience Tuscany’s highlights with expert guides, delicious local food, and charming towns—all within a well-paced, small-group setting. Perfect for those seeking an authentic, memorable day out from Florence.