Florence: Siena, San Gimignano and Chianti Small Group Tour

Discover Tuscany’s Charms on a Small Group Tour

The Florence: Siena, San Gimignano, and Chianti Small Group Tour offers an engaging full-day experience through some of Tuscany’s most captivating towns. Priced at a reasonable cost, this 9-hour guided trip is ideal for travelers seeking an intimate atmosphere, with groups limited to 25 people. The tour departs from Piazzale Montelungo in Florence, at 7:45 AM, and offers a combination of guided walks, free time, and delicious food and wine tastings.

What makes this tour stand out is its well-balanced itinerary, allowing deep exploration of Siena and San Gimignano, plus a stop in the picturesque Chianti countryside. The expert guides bring the towns’ stories to life, while the included lunch with local wines gives a genuine taste of Tuscany. A notable strength is the small group setting, which creates a relaxed, personalized experience, though it’s not suitable for those with mobility issues.

This tour is perfect for those who want to see Tuscany’s highlights without the hassle of independent planning. It combines sightseeing, cultural insights, and culinary delights into one seamless day. However, travelers should be prepared for a day of walking and driving, and keep in mind that Siena Cathedral is not accessible on Sundays or during religious celebrations.

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Key Points

• Includes Siena, San Gimignano, and Chianti in a single day
• Guided walking tour in Siena with skip-the-line access to the cathedral
• Tastings of local wines and a hearty Tuscan lunch at a family-owned winery
• Stroll through San Gimignano’s medieval streets and admire its famous towers
• Small-group size ensures more personalized attention
• Departure at 7:45 AM from Florence, returning late afternoon

From the Meet Point to the Tuscan Countryside

The tour begins at Piazzale Montelungo, located opposite the parking lot, about an 8-minute walk from Florence SMN Train Station. The meeting point is marked by a red flag or a sign with the activity provider’s logo. The coach ride to Siena lasts about 1.5 hours, during which the guide shares some introductory insights about the day ahead.

Traveling in a comfortable minibus, the small group enjoys scenic views of the Tuscan hills, olive groves, and vineyards. This relaxed start helps set the tone for a full day of discovery in some of Italy’s most iconic towns.

Exploring Siena’s Historic Center with a Guide

Upon arriving in Siena, the guided walking tour lasts approximately 75 minutes. The guide leads the group through narrow medieval streets, sharing stories about Siena’s history and its famous Palio horse race held twice a year in the shell-shaped Piazza del Campo.

Guests get skip-the-line access to the Siena Cathedral, a magnificent example of Gothic architecture. Inside, visitors can admire intricate artworks and stunning details, although access is limited on Sundays and religious holidays. The walking tour also includes passing through lively squares and learning about Siena’s rivalries and traditions, making history come alive.

After the guided exploration, there’s about an hour of free time. Visitors often use this to shop for local crafts, browse cafes, or simply enjoy Siena’s authentic ambiance at their own pace.

A Taste of Tuscan Rural Life at a Family-Owned Winery

Following Siena, the group drives about 35 minutes through serene Tuscan scenery to reach a family-owned wine estate. Here, the focus is on local wines and authentic countryside hospitality. The winery provides a hearty Tuscan lunch that includes assorted cold cuts, cheeses, bruschetta, pasta or soup, and dessert, all paired with the estate’s own wines and olive oil.

The lunch is more filling than a typical light snack, making it a satisfying meal that pairs beautifully with wine tastings. Guests enjoy relaxed conversations with the winery staff, learning about olive oil and wine production, and appreciating the stunning views of vineyards and rolling hills.

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Discovering San Gimignano’s Medieval Skyline

After lunch, the journey continues with a 35-minute drive to San Gimignano. Known for its skyscraper-like medieval towers, the town’s main street is lined with shops selling local crafts, gelato, and souvenirs. The free time of about 1.5 hours allows visitors to explore independently.

Highlights include visiting the Collegiata, the main church, and photographing the town’s iconic skyline from different vantage points. Sampling gelato in San Gimignano is a popular activity, and the views of Tuscan countryside from the town walls are truly picturesque.

Return Journey and Practical Details

The coach ride back to Florence takes approximately 75 minutes, giving the group time to relax after a full day of sightseeing. The tour concludes at Piazzale Montelungo in late afternoon, making it convenient for travelers to continue exploring Florence or return to their accommodation.

The entire experience is designed to balance guided discovery with free exploration, giving travelers a rich taste of Tuscany’s culture, scenery, and flavors.

The Experience with Expert Guides and Smooth Logistics

Throughout the day, guides like Lorenzo and Francesco receive high praise for their knowledge, storytelling skills, and friendly demeanor. They provide useful tips, manage pacing, and ensure all guests feel comfortable and engaged.

The driver Alessio or Nino, depending on the day, expertly navigates the winding roads, making the journey comfortable and safe. The small group size allows for easier movement through towns and more personal interactions with guides and local hosts.

Practical Tips and Accessibility

The tour operates rain or shine, with weather-appropriate clothing recommended. It is not suitable for mobility-impaired or wheelchair users due to the walking involved in Siena and San Gimignano. Guests should bring their passport or ID, and those with dietary restrictions should request vegetarian options when booking.

Why This Tour Works for You

With an overall rating of 4.9 out of 5 from 433 reviews, this tour clearly resonates with travelers who value expert guides, authentic experiences, and a relaxed pace. The small group setting is often cited as a key advantage, making sightseeing less rushed and more intimate.

The combination of cultural visits, wine tasting, and country lunch offers a comprehensive and enjoyable Tuscan day trip. While it packs a lot into one day, the pacing allows for ample free time to soak in the atmosphere and take photos.

Florence: Siena, San Gimignano, and Chianti Small Group Tour

This tour provides an excellent way to see Tuscany’s highlights in one day, especially for those short on time in Florence. The guided walking tours, wine tasting, and local lunch create a well-rounded experience. The expert guides and smooth logistics ensure a comfortable, enriching day.

The limited group size enhances the experience, fostering more interaction and easier navigation through crowded streets. The inclusion of skip-the-line access to Siena’s cathedral and the stunning countryside views are real pluses.

However, travelers should be prepared for a full day of walking and driving. The Siena Cathedral’s inaccessibility on Sundays and during religious events** is a small consideration. This tour offers a fantastic snapshot of Tuscany’s towns and traditions, making it a highly recommended choice for first-time visitors.

Frequently Asked Questions

What is included in the tour price?
The price covers transportation in a minibus, guided tours in Siena, wine tasting, and a Tuscan lunch. Entrance fees like Siena Cathedral are included, but check if specific upgrades are available.

What time does the tour start and end?
The tour departs at 7:45 AM from Florence and returns in the late afternoon, typically around 5:30–6:00 PM.

Is the tour suitable for children or those with mobility issues?
No, it’s not suitable for people with mobility impairments or wheelchair users due to walking in Siena and San Gimignano. Young children may find the full day lengthy.

Do I need to bring anything special?
Guests should bring their passport or ID and dress in weather-appropriate clothing. Comfortable shoes are recommended for walking.

Can dietary restrictions be accommodated?
Yes, a vegetarian menu can be arranged if requested at the time of booking.

What is the group size?
Limited to up to 25 participants, ensuring a more personal experience compared to larger tours.

How is the guide?
The guides are consistently praised for their knowledge, friendliness, and storytelling ability. They provide helpful tips and make the experience enjoyable.

What if it rains?
The tour operates rain or shine, so come prepared for the weather.

Is the Siena Cathedral accessible on Sundays?
No, visits to Siena Cathedral are not available on Sundays or during religious celebrations.

What makes this tour stand out from others?
The small-group size, expert guides, and the balanced itinerary that combines culture, scenery, and food make this tour a standout choice for exploring Tuscany in one day.

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