Private tour Siena, San Gimignano and Monteriggioni, lunch in the cellar

Explore Tuscany’s Historic Gems with a Private Guide

This private tour from Florence offers a personalized journey through some of Tuscany’s most iconic spots. For $887.34 per group (up to 7 people), visitors enjoy a flexible itinerary, led by an English-speaking driver. The experience lasts approximately 8 to 9 hours, making it a comfortable full-day escape into the Tuscan countryside. The tour includes transportation in an air-conditioned vehicle with WiFi, with pickup and return to Florence included. While lunch and wine tasting are not part of the base price, the stops here are highlights, especially at a family-run winery.

What makes this tour particularly attractive is its small-group, private format, allowing for greater flexibility and more personalized attention. The consistent 5.0/5 rating from 8 reviews underscores its high value and enjoyable experience. It suits travelers who want a comprehensive, intimate exploration of Tuscany’s famous towns with skip-the-line access to key attractions and plenty of free time to soak in the scenery.

Key Points

• Private, fully customizable day trip starting from Florence with pickup included
• Visits to Siena, Monteriggioni, and San Gimignano, all UNESCO World Heritage sites
• Includes a walk through Siena’s historic center, including the Basilica of San Domenico and Piazza del Campo
• Short stop at Monteriggioni’s castle-like village, a fairy-tale setting
• Time for wine tasting and a lunch in a family-run winery at Sant’Appiano (lunch not included in tour price)
• Admire panoramic views of the Tuscan countryside from San Gimignano and taste Italy’s finest ice cream
• Tour duration is about 8 to 9 hours, with comfortable private transport and WiFi onboard
• Highly praised guides, especially Florian, known for his knowledge and friendly approach

From Florence to Siena’s Historic Downtown

The tour begins with a roughly 1.5-hour drive from Florence to Siena’s city center, a UNESCO World Heritage Site. The guided walk includes visits to the Basilica of San Domenico, renowned for its Gothic architecture and the relic of Santa Caterina. The Piazza del Campo welcomes visitors with its distinctive shell shape, and it hosts the famous Palio horse race held twice each summer.

The exterior of Siena’s Duomo, the Metropolitan Cathedral of Santa Maria Assunta, is also included in the visit. While internal visits to the Duomo are optional and not included in the price, guests can appreciate its stunning façade and the chance to admire its architectural details. The guided exploration ensures that visitors get a clear sense of Siena’s cultural importance and lively atmosphere.

Monteriggioni’s Enchanting Castle-Like Village

After Siena, a short 25-minute drive brings travelers to Monteriggioni, a tiny medieval village that feels straight out of a fairy tale. The castle walls and towers have remained remarkably intact since the 13th century, giving a sense of stepping back in time.

The around 30-minute visit emphasizes the magical ambiance of the village, with its few streets and impressive fortifications. Its small size means there’s little time to explore, but the visual impact of its well-preserved ramparts and towers leaves a lasting impression. It’s an ideal stop for those who appreciate medieval architecture and scenic views.

Wine Tasting and Lunch at Sant’Appiano

The itinerary includes a 1 hour and 30 minutes stop at a family-run winery, Fattoria Sant’Appiano. The lunch and wine tasting are optional and not included in the tour price, but this is often highlighted as a favorite part of the day. The wine cellar offers a chance to sample Chianti wines, and the lunch in the cellar provides a taste of authentic Tuscan cuisine in a warm, familial setting.

Guides like Florian are praised for their knowledge about local wines and for explaining the winemaking process, adding educational value to the tasting. The experience offers a relaxing break amidst Tuscan vineyards, with the chance to sample some of Italy’s best wines in a genuine setting.

The Charm of San Gimignano’s Medieval Skyline

Following the winery stop, the tour moves on to San Gimignano, about 40 minutes away. Known for its medieval towers, this town is a UNESCO site that has retained its historic charm since the 14th century.

Visitors get a 1-hour exploration of the town’s narrow streets, towers, and piazzas. The viewpoints offer spectacular panoramas of the Tuscan countryside. San Gimignano is also famous for tasting the best ice cream in Italy, a treat that visitors often indulge in while strolling through its well-preserved medieval streets.

Panoramic Views and Michelangelo’s Square

The tour concludes with a visit to Piazzale Michelangelo in Florence, offering one last stunning vista of the city. From this vantage point, visitors can look out over Florence’s rooftops and famous landmarks, making it a perfect photo opportunity before returning to the starting point.

The private transportation makes the return trip smooth, and with WiFi and bottled water included, travelers can relax comfortably during the journey. The drop-off back in Florence wraps up the day, giving a convenient end to the experience.

The Transport and Guide Experience

Throughout the tour, a private, air-conditioned vehicle ensures a comfortable ride between stops. The WiFi onboard adds convenience, allowing for sharing photos or quick messages during transit. The guide, Florian, receives high praise for his knowledge, friendliness, and patience, making the experience more engaging and informative.

His ability to point out interesting details and share background stories enhances the visit to each site. The small-group format ensures a personalized experience, with ample opportunity to ask questions and tailor the timing to suit your interests.

The Flexibility and Pace of the Tour

This private tour offers significant flexibility in scheduling and pacing. Stops are timed to allow for photo opportunities, short walks, and relaxing breaks. The lunch and tasting at the winery are optional but often considered a highlight, and guides are accommodating to your preferences.

While the tour covers several locations in one day, the pacing remains comfortable—enough time to enjoy each stop without feeling rushed. Travelers with limited mobility should consider the walking involved, especially at Siena and San Gimignano.

The Value and Booking Insights

At $887.34 for a group of up to 7, this tour provides a cost-effective way to see multiple Tuscan highlights in one day with personalized service. Booking is typically done 74 days in advance, reflecting its popularity.

The free cancellation policy allows for flexibility if plans change, making it a practical choice for those who want a well-organized, intimate experience with high customer ratings.

Who Will Enjoy This Tour?

This private, guided experience is ideal for small groups or families seeking an authentic and relaxed exploration of Tuscany. It suits those interested in history, architecture, wine, and scenic views, with the added comfort of private transport and flexible timings.

Anyone who appreciates personalized service and wants to avoid large tour groups will find this itinerary particularly rewarding. The knowledgeable guide and carefully curated stops make for a memorable day in Tuscany.

Frequently Asked Questions

Is lunch included in the tour?
No, lunch at the winery is optional and not included in the tour price.

Can I visit the Siena Duomo inside?
An internal visit to Siena’s Duomo is possible but not included in the base price and requires an additional ticket.

Is the tour suitable for children?
Most travelers can participate, and the tour is private, allowing customization. For specific needs like child seats, please request at booking.

What languages are guides available in?
The driver and guide speak English.

How long are the stops at each location?
Stops last approximately 1.5 hours in Siena, 30 minutes in Monteriggioni, 1.5 hours at the winery, and 1 hour in San Gimignano, making for a well-paced day.