Exploring the enchanting regions outside of Florence, this private tour offers travelers an immersive experience through Tuscany’s most captivating destinations. From the medieval wonders of Siena to the picturesque hills of Chianti, the journey promises to unveil the true heart of this remarkable Italian province. Whether seeking to uncover Siena’s historic legacy or savor the flavors of a traditional Tuscan lunch paired with fine regional wines, this exclusive excursion caters to the discerning explorer. What hidden gems await in this private tour of Tuscany’s gems?

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Key Points

Explore the historic towns of Siena, San Gimignano, and the Chianti wine region on a private day tour from Florence.
Visit the UNESCO-listed Siena and its iconic Duomo, and enjoy free time to wander the charming streets.
Discover the "Town of Fine Towers," San Gimignano, and savor renowned Tuscan gelato.
Indulge in a guided wine tasting of Chianti Classico wines and a traditional Tuscan lunch.
Enjoy the flexibility and convenience of a private tour with transportation included.

You can check availability for your dates here:

Tour Overview

The "Florence: Private Siena, San Gimignano & Chianti Tour" is a comprehensive 9-hour excursion that allows visitors to discover the historic cities, medieval villages, and picturesque Chianti countryside of Tuscany.

Priced at $479.84 per person, the private tour includes transportation, a guided wine tasting, and a traditional Tuscan lunch.

Highlights include exploring the UNESCO-listed historic center of Siena, wandering the ancient walls of Monteriggioni, and visiting the charming town of San Gimignano.

With free cancellation up to 24 hours in advance and a reserve now, pay later option, this tour offers flexibility and convenience for travelers.

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Monteriggioni: Medieval Fortress Village

Monteriggioni stands as a captivating medieval fortress village, its ancient walls and towers rising majestically against the rolling Tuscan landscape. Visitors can explore the well-preserved medieval architecture, admiring the strategic design and panoramic vistas. The village offers a glimpse into Tuscan history, with its quaint squares, cobblestone streets, and traditional shops.

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Stepping back in time, Monteriggioni transports visitors to a bygone era, inviting them to enjoy the captivating medieval ambiance of this picturesque Tuscan gem.

Siena: Exploring the Historic Center

After experiencing the enchanting medieval village of Monteriggioni, the tour continues to the historic city of Siena.

The group stops for a photo op, capturing the city’s iconic Duomo and Piazza del Campo, a UNESCO World Heritage site. Guests then have two hours of free time to explore Siena’s winding streets, admire its Gothic architecture, and indulge in local delicacies.

Whether browsing quaint shops, visiting the Basilica of San Domenico, or simply soaking in the vibrant atmosphere, the city’s timeless charm captivates all who visit.

The tour provides an opportunity to take in Siena’s rich history and cultural heritage.

Chianti Hills: Wine Tasting and Tuscan Lunch

As the tour leaves the medieval village of Monteriggioni behind, the group eagerly anticipates the next stop in the heart of the Chianti wine region.

The scenic drive through the rolling Tuscan hills sets the stage for a delightful wine tasting experience.

Upon arrival, a knowledgeable guide leads the group through a sampling of the region’s renowned Chianti Classico wines.

Complementing the tasting, a traditional Tuscan lunch showcases the area’s fresh, locally sourced ingredients.

The perfect pairing of fine wine and authentic cuisine immerses the travelers in the essence of Tuscany’s renowned culinary and viticultural traditions.

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San Gimignano: The Town of Fine Towers

Leaving the picturesque Chianti hills behind, the group eagerly anticipates their next destination – the medieval town of San Gimignano, known as the "Town of Fine Towers".

Towering over the surrounding landscape, the town’s iconic skyline of 14 preserved medieval towers stands as a testament to its prosperous past.

Wandering through the charming streets, visitors marvel at the well-preserved Gothic and Romanesque architecture, including the Duomo and the Palazzo del Podestà.

The town is also renowned for its award-winning gelato, offering a delightful treat after exploring the historic sights.

A delightful treat after exploring the historic sights, the town is renowned for its award-winning gelato.

With free time to roam, the group can truly enjoy the town’s timeless allure.

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Highlights of the Experience

The tour offers a remarkable opportunity to take in the rich cultural tapestry of Tuscany.

Visitors will discover the UNESCO-listed historic center of Siena, with its striking Gothic architecture and lively piazza.

In Monteriggioni, they’ll explore the ancient fortress walls and enjoy panoramic vistas.

The tour also includes a guided wine tasting in the Chianti hills, where guests can savor local vintages paired with a traditional Tuscan lunch.

Finally, the enchanting medieval town of San Gimignano, known for its iconic towers and award-winning gelato, provides a charming finale to the day’s adventures.

Inclusions and Amenities

This tour provides a comprehensive package of inclusions and amenities to ensure an exceptional Tuscan experience.

The tour is led by an informative English-speaking guide who provides insightful commentary throughout the day. Guests are transported in a luxury private vehicle, ensuring a comfortable and hassle-free journey.

Guests are transported in a luxury private vehicle, ensuring a comfortable and hassle-free journey, while an informative English-speaking guide provides insightful commentary throughout the day.

The experience also includes:

A guided wine tasting featuring local Chianti Classico varieties and a traditional Tuscan lunch made with fresh, locally sourced ingredients.
Free time to explore the charming medieval towns of Siena, Monteriggioni, and San Gimignano at one’s own pace.
All fuel and parking fees are covered, allowing for a seamless and carefree adventure.

Important Information

Guests should meet at Piazza della Calza by Porta Romana, near the San Giovanni Battista della Calza church, at 8:30 am to begin the tour.

Comfortable shoes, a sun hat, a camera, and water are recommended. The tour isn’t suitable for wheelchair users.

Guests can customize the itinerary to suit their preferences and should notify the team about any dietary needs or minors in the group.

The tour includes private transportation in a luxury vehicle, an informative English-speaking guide/driver, a wine tasting, and a Tuscan lunch, with free time to explore Siena, Monteriggioni, and San Gimignano.

The Sum Up

Set out on a captivating journey through Tuscany’s enchanting landscapes and historic towns. Enjoy the rich heritage of Siena, marvel at the iconic towers of San Gimignano, and savor the flavors of Chianti with a guided wine tasting and traditional Tuscan lunch. This private tour from Florence offers a personalized experience, allowing you to create unforgettable memories in the heart of this captivating region.