San Gimignano, Siena and Chianti Small Group Wine Tour

The San Gimignano, Siena, and Chianti Small Group Wine Tour offers an immersive experience into the heart of Tuscany. Priced at $168.36 per person, this 9-hour journey departs from Florence and features visits to iconic towns, wine tasting, and a delicious Tuscan lunch. The tour operates with a small group of up to 30 people, ensuring a more personalized experience, and it’s perfect for those who want a well-rounded day exploring Tuscany’s highlights at a relaxed pace. While reviews praise the knowledgeable guides, stunning scenery, and great value, some note that certain stops—like Siena’s free exploration—may feel a bit rushed.

This tour suits travelers seeking a mix of guided sightseeing and free time, especially those interested in wine tasting and authentic local cuisine. It does involve a fair amount of walking and some weather considerations, but overall, it caters well to curious adventurers wanting to see Tuscany’s most famous spots with the comfort of transportation and expert narration.

Key Points

• Full-day experience exploring Siena, San Gimignano, and Chianti from Florence
• Includes wine tasting in a typical Tuscan winery with 5 wines and artisanal products
• Delicious Tuscan lunch featuring lasagne al tartufo, ribollita, and cantucci with Vin Santo
• Guided tours with free time in San Gimignano and Siena
• Small group size (up to 30 travelers) for a more intimate experience
• Departs at 8:30 am from Piazza del Duomo in Florence

Starting Point and Duration of the Tour

The tour begins at Piazza del Duomo, Florence, at 8:30 am, with the group gathering near public transportation options. The entire experience lasts approximately 9 hours, wrapping up back at the starting point. The schedule balances sightseeing, tasting, and leisure, with some stops offering free time of up to 1-2 hours for independent exploration.

Travelers should prepare for an early start and a long day, but the well-paced itinerary helps prevent fatigue. The tour operates in all weather conditions, so dressing appropriately for the day’s climate is recommended.

Exploring Siena’s Medieval Charm

Siena’s old town forms a core part of this experience. The guides lead visitors through the historic city center, focusing on highlights like the Siena Cathedral (Duomo), an impressive Gothic-Romanesque church with a facade in black and white marble and artworks by Donatello, Pinturicchio, and Nicola Pisano.

The Piazza del Campo, famous for hosting the Palio di Siena, is a hub for civic life and celebrations. The shell-shaped square is surrounded by medieval palaces and is ideal for strolling and soaking in local atmosphere. An ancient fountain in the square, featuring wolves, symbolizes Siena’s connection to ancient Rome, although the original carved panels are housed elsewhere for preservation.

The Palazzo Pubblico and Museo Civico showcase frescoes and paintings, including the renowned Maestà. Sightseeing here combines guided narration with plenty of free time, though some guests find the visit slightly brief considering Siena’s richness.

The Allure of San Gimignano’s Skyline

San Gimignano earns its nickname “Manhattan of the Middle Ages” thanks to its skyline of medieval towers. The tour provides two hours of free time in this UNESCO World Heritage site, allowing visitors to wander at their own pace.

Most choose to visit the Duomo di San Gimignano, an impeccably preserved church with medieval frescoes, or explore Piazza della Cisterna, a lively square with a wheel at its center and historic palaces facing it. The town’s narrow alleys and craft workshops invite relaxed browsing, with a popular stop being the Gelateria Dondoli, known for serving some of the world’s best ice cream.

For those eager for panoramic views, climbing Palazzo Pubblico’s Torre Grossa for stunning vistas of the towers and Tuscan landscape is a highlight, though the climb takes about 30 minutes and is not included in the cost.

Chianti Wine Tasting in the Tuscan Countryside

A major highlight is the wine tasting experience at Agricola Poggio Ai Laghi, set amidst the rolling hills of Chianti. The private tour of the winery culminates in sampling five wines paired with artisanal olive oils, including truffle and spicy pepper varieties, plus Gold Seal balsamic vinegar.

The wine tasting lasts about one hour and forty minutes, offering guests a chance to learn about local production methods and savor authentic flavors. The winery’s scenic setting enhances the experience, making it a memorable part of the day.

The lunch at the winery is a Tuscan feast with cheese, cured meats, bruschetta, lasagne al tartufo, and hearty ribollita. For dessert, guests indulge in cantucci dipped in Vin Santo, rounding out the culinary experience.

Free Time and Discovering San Gimignano

During the free time in San Gimignano, visitors can explore its medieval streets, towers, and churches. The Collegiata di Santa Maria Assunta, located in the main square, presents an extraordinary medieval church with original walls and artwork, and is a quick visit option.

Piazza della Cisterna offers picturesque views, historical architecture, and lively cafes. For those wanting a panoramic view, climbing the Torre Grossa in Palazzo del Popolo is popular, providing sweeping vistas of the town’s skyline of towers and the surrounding countryside.

Practicalities and Group Size

This tour maintains an intimate group environment with a maximum of 30 travelers, allowing for more personalized attention from the expert tour leader. The transportation is via comfortable bus, enabling smooth travel between Florence and the Tuscan towns.

Participants should expect a moderate amount of walking and be prepared for changeable weather. The tour includes free time for individual exploration, so comfortable shoes and weather-appropriate clothing are recommended.

Food and Drink Highlights

The wine tasting in Chianti is a major draw, featuring five wines with artisanal oils and balsamic. The lunch offers a classic Tuscan menu, emphasizing local ingredients and traditional recipes, with lasagne al tartufo and ribollita providing hearty flavors.

Guests have praised the quality of the wine and deliciousness of the meal, though some reviews mention that at the winery, pasta costs extra and that lunch service can be slow. Despite this, the overall culinary experience aligns with Tuscan traditions and adds significant value.

Final Assessment: Who Will Appreciate This Tour?

This full-day Tuscan adventure appeals to those who want a balanced mix of guided sightseeing and free exploration, with a focus on wine, food, and iconic towns. Visitors who appreciate stunning scenery, historical architecture, and local flavors will find this tour rewarding.

While some might wish for longer in Siena and San Gimignano, the included wine tasting, scenic views, and cultural highlights make it a solid choice. It’s especially suitable for travelers seeking a relaxed yet comprehensive introduction to Tuscany’s best-known sites with the convenience of transportation and expert guides.

Frequently Asked Questions

Is hotel pickup included in this tour?
No, the tour starts at Piazza del Duomo in Florence, and hotel pickup is not provided.

What is the duration of the wine tasting?
The wine tasting lasts about one hour and forty minutes at Agricola Poggio Ai Laghi.

Are guided tours included in Siena and San Gimignano?
No, the tour provides guided exploration in Siena but free time in San Gimignano; there are no guided tours inside the towns beyond the initial exploration.

What should I wear?
Comfortable shoes are recommended due to walking on cobblestone streets and slight inclines, along with weather-appropriate clothing.

Can I visit Siena Cathedral?
Entry is not included in the ticket price, so visitors can choose to visit it at their own expense, depending on opening times.

What is the group size?
The maximum group size is 30 travelers, ensuring a more engaging experience.

Is this tour suitable for children or elderly travelers?
Most travelers can participate, but some walking and physical activity are involved, so consider mobility levels.

Does the tour operate in bad weather?
Yes, the tour operates in all weather conditions. Dress appropriately for potential rain or cold.

What is the cancellation policy?
You can cancel free of charge up to 24 hours in advance for a full refund.

Who is the experience provider?
The tour is provided by myTour in Italy.