Tucked away in the heart of Tuscany, this private tour from Florence offers travelers a chance to enjoy the region’s rich history, captivating landscapes, and renowned culinary delights. From the medieval splendor of Siena’s Piazza del Campo to the iconic skyline of San Gimignano, this intimate journey promises an unforgettable experience. Guests will also have the opportunity to explore the charming town of Monteriggioni, savor a traditional Tuscan lunch, and indulge in a delightful wine tasting featuring the area’s signature VERNACCIA and local olive oil. With a maximum group size of 8, this tour ensures a personalized and authentic exploration of Tuscany’s cultural and gastronomic treasures. What awaits beyond the walls of Florence is a world of enchantment, waiting to be discovered.
Key Points

- Explore the historic centers of Siena, Monteriggioni, and San Gimignano on a private tour from Florence, lasting approximately 9.5 hours.
- Experience a traditional Tuscan lunch and wine tasting at a local winery, including sampling of VERNACCIA white wine and olive oil.
- Visit the well-preserved medieval walls of Monteriggioni and the iconic skyline of San Gimignano, known as the ‘Medieval Manhattan.’
- Enjoy ample free time for shopping and exploration in each village, with a guided tour of Siena’s Piazza del Campo and Duomo.
- Transportation in a premium, air-conditioned van with an English-speaking driver, with a maximum group size of 8 people.
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Contents
- Key Points
- Tour Overview
- Itinerary Highlights
- Culinary Experience
- Transportation and Group Details
- Important Information
- Siena Discovery
- Monteriggioni and San Gimignano
- Wine Tasting and Local Delicacies
- Frequently Asked Questions
- Is Photography Allowed During the Tour?
- Can I Bring My Own Food and Drinks on the Tour?
- Is There an Option to Extend the Tour Duration?
- What Is the Cancellation Policy for This Tour?
- Is There a Discount for Groups Larger Than 8 People?
- Recap
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Tour Overview

This private tour offers a comprehensive exploration of the picturesque Tuscan towns of Siena, Monteriggioni, and San Gimignano, departing from Florence and lasting approximately 9.5 hours.
Priced at €439.00 per person, the tour includes free cancellation up to 24 hours in advance and a reserve now, pay later option.
Travelers will experience the historic centers of these charming villages, visiting ancient churches, medieval castles, and picturesque hamlets.
In Siena, a guided tour showcases the iconic Piazza del Campo and Piazza del Duomo. Ample free time is provided for shopping and independent exploration in each destination.
The tour also includes a traditional Tuscan lunch and wine tasting at a local winery.
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Itinerary Highlights

Embarking on this private tour, travelers experience the historic centers of Siena, Monteriggioni, and San Gimignano, visiting ancient churches, medieval castles, and picturesque hamlets along the way.
In Siena, a guided tour takes them to see the famous Piazza del Campo and Piazza del Duomo. They’ll then have free time in each village to shop or explore the local sights at their leisure.
From the well-preserved medieval walls of Monteriggioni to the iconic skyline of San Gimignano, this itinerary offers a comprehensive glimpse into the rich history and architectural wonders of Tuscany’s most enchanting destinations.
Culinary Experience

The private tour includes a typical Tuscan lunch at a local restaurant, where travelers can savor authentic cuisine and local delicacies.
Following the meal, the group will visit a nearby winery for a tasting of the region’s renowned VERNACCIA white wine and a sampling of local olive oil, providing an immersive culinary experience that showcases the flavors of Tuscany.
This experience allows guests to:
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Indulge in the rich, traditional flavors of Tuscan gastronomy.
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Discover the unique characteristics of the VERNACCIA grape and the region’s renowned olive oil.
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Gain a deeper appreciation for the local culinary traditions and terroir of the Tuscan countryside.
Transportation and Group Details

Travelers will be transported in a premium, air-conditioned van driven by an English-speaking driver during the private tour.
The group size is limited to a maximum of 8 persons, with a minimum of 2 required for the tour to operate.
Pick-up can be arranged upon request, making it convenient for participants to join the experience.
The small group size ensures a personalized and intimate exploration of the Tuscan countryside.
Whether travelers are part of a larger party or prefer a more exclusive adventure, the transportation and group details are designed to provide a comfortable and enjoyable journey through Siena, San Gimignano, and Monteriggioni.
More Great Tours NearbyImportant Information

The tour commences promptly at 8:15 AM daily, with participants meeting the driver outside Cantina Antinori. Comfortable footwear is recommended to ensure a smooth and enjoyable experience navigating the historic villages. Plus, pets and smoking are prohibited during the tour. These tour details and guidelines help ensure a seamless and memorable private excursion through the picturesque Tuscan countryside.
The meeting point at Cantina Antinori is conveniently located, allowing for a timely departure.
To further enhance the experience, the tour:
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Provides a maximum group size of 8 persons, ensuring personalized attention.
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Offers a pick-up service upon request for added convenience.
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Maintains a policy of free cancellation up to 24 hours in advance for a full refund.
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Siena Discovery

Often considered the crown jewel of the tour, Siena enchants visitors with its beautifully preserved medieval architecture and vibrant cultural heritage.
During the guided tour, you’ll stroll through Piazza del Campo, the iconic shell-shaped square that’s home to the annual Palio horse race. You’ll then marvel at the stunning Duomo, a masterpiece of Italian Gothic architecture with intricate marble striations. Your guide will share the fascinating history of these iconic landmarks, bringing Siena’s past to life.
With ample free time, you can explore the charming alleys, browse local boutiques, and savor authentic Sienese delicacies at your own pace, enjoying the city’s timeless atmosphere.
Monteriggioni and San Gimignano

After exploring the enchanting city of Siena, the tour continues to the walled medieval town of Monteriggioni, known for its stunningly preserved defensive walls and towers.
Guests then journey to the iconic hilltop village of San Gimignano, famed for its striking skyline of medieval towers that have earned it the nickname ‘the Medieval Manhattan.’
In San Gimignano, visitors can:
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Wander the charming cobblestone streets and visit the Duomo di San Gimignano, a Romanesque cathedral with remarkable frescoes.
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Discover artisan shops selling local delicacies, handicrafts, and the renowned Vernaccia di San Gimignano white wine.
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Climb to the top of one of the iconic towers for panoramic views over the picturesque Tuscan countryside.
Wine Tasting and Local Delicacies

At the heart of this Tuscan discovery lies the captivating wine tasting experience, where guests explore the rich flavors and history of the region’s renowned varietals.
Guests savor the crisp notes of the VERNACCIA white wine, renowned for its distinctive terroir, as well as sample the robust, full-bodied red wines that have made this area a celebrated wine-producing destination.
Alongside the wine tasting, visitors indulge in a spread of authentic Tuscan delicacies, including locally sourced artisanal cheeses, cured meats, and other regional specialties, providing a comprehensive culinary journey through the flavors of this iconic Italian landscape.
Frequently Asked Questions

Is Photography Allowed During the Tour?
Photography is generally allowed during the tour. Guests are free to take photos at the various locations visited, such as ancient churches, medieval castles, and picturesque villages. However, photography may be restricted in some areas, so guests should follow the guide’s instructions.
Can I Bring My Own Food and Drinks on the Tour?
No, you generally cannot bring your own food and drinks on the tour. The tour includes a typical Tuscan lunch at a local restaurant as well as a wine tasting, so bringing your own items is not permitted.
Is There an Option to Extend the Tour Duration?
The tour operator doesn’t explicitly offer an option to extend the tour duration. However, customers can inquire about this possibility when booking the tour. Any extension would likely incur an additional fee.
What Is the Cancellation Policy for This Tour?
The tour has a free cancellation policy up to 24 hours in advance for a full refund. Customers can cancel their booking and receive a complete reimbursement if they notify the provider at least a day before the scheduled departure.
Is There a Discount for Groups Larger Than 8 People?
The tour has a fixed maximum group size of 8 persons and doesn’t offer discounts for larger groups. The price remains the same regardless of the total number of participants, as stated in the tour details.
From Florence: Private Siena, San Gimignano + Wine Tasting
Recap
Enjoy the captivating landscapes and rich heritage of Tuscany on this private tour from Florence.
Discover the enchanting medieval towns of Siena, Monteriggioni, and San Gimignano, savoring a traditional Tuscan lunch and indulging in a delightful wine tasting.
With a small group size, this personalized journey offers an intimate experience that celebrates the region’s culture, gastronomy, and stunning vistas.
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