Exploring the enchanting Siena and Chianti region by private luxury van offers an unforgettable day trip from Florence. Led by a knowledgeable guide, visitors will discover Siena’s UNESCO-listed historic center, iconic sites like Piazza del Campo, and the stunning Siena Cathedral. The scenic drive through Chianti’s vineyards and olive groves leads to family-owned wineries, where exquisite wine tastings and authentic Tuscan cuisine await. This seamless excursion provides an immersive experience of Tuscany’s rich culture and renowned winemaking traditions.
Key Points

- Full-day private luxury van excursion from Florence to explore Siena’s historic center and the scenic Chianti region, with opportunities to taste local wines and culinary delights.
- Guided walking tour of Siena’s UNESCO-listed historic center, including visits to the iconic Piazza del Campo and the impressive Siena Cathedral.
- Scenic drive through the Chianti countryside, showcasing lush vineyards, olive groves, and picturesque stone farmhouses.
- Tastings at family-owned wineries and visits to olive oil and balsamic vinegar producers, offering an immersive culinary experience.
- Seamless experience with free hotel pickup and drop-off, as well as included admission tickets to top landmarks.
Tour Overview

This private luxury van excursion from Florence to Siena and Chianti offers a full-day experience ideal for families.
With 100% traveler recommendation from 10 reviews, the tour includes free hotel pickup and drop-off.
Guests will explore Siena’s UNESCO-listed historic center with a local guide, visiting Piazza del Campo and the medieval cathedral.
The scenic drive through Chianti provides views of vineyards and olive groves.
Travelers can taste Chianti wines, olive oil, and balsamic vinegar, as well as enjoy lunch at a local restaurant or family-owned vineyard.
An English-speaking driver, bottled water, and admission tickets are included.
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Exploring Siena’s Historic Center
After exploring the scenic Chianti countryside, the excursion takes guests to the historic city of Siena.
A local guide leads visitors on a walking tour of Siena’s UNESCO-listed historic center. The tour includes Piazza del Campo, the iconic medieval town square, and the impressive Siena Cathedral.
Guests will stroll along the city’s historic boulevards, discovering boutiques, cafes, and architectural gems.
The excursion offers an immersive experience, allowing visitors to soak in Siena’s rich history and medieval atmosphere.
With admission tickets included, the tour provides seamless access to the city’s top landmarks.
Discovering Piazza Del Campo and the Cathedral

Visitors first encounter the iconic Piazza del Campo, Siena’s expansive medieval town square. Shaped like a scallop shell, the plaza hosts the famous Palio horse race twice a year.
Nearby stands the magnificent Siena Cathedral, a Romanesque-Gothic masterpiece adorned with striped marble and intricate statues. Travelers can explore the cathedral’s interior, admiring the ornate pulpit, stained glass windows, and the mosaic-tiled floor.
They’ll also learn about the cathedral’s history and significance to Sienese culture from the knowledgeable local guide. With ample time to wander, guests discover hidden gems along the square’s historic streets and charming boutiques.
Walking Tour of Siena’s Boutiques and Boulevards

With the grandeur of Piazza del Campo and the Siena Cathedral now explored, the tour moves on to uncover the city’s charming boutiques and historic boulevards.
The walking tour weaves through the narrow streets, showcasing local artisanal shops and centuries-old landmarks.
Highlights include:
- Browsing handcrafted leather goods, ceramics, and other unique Sienese souvenirs
- Admiring the ornate architecture and medieval ambiance of the city’s main thoroughfares
- Exploring hidden corners and experiencing the authentic spirit of Siena’s vibrant city center
The immersive exploration provides an intimate look at the daily life and rich cultural heritage that defines this Tuscan gem.
Scenic Drive Through Chianti’s Vineyards and Olive Groves

The scenic drive through Chianti’s vineyards and olive groves offers a captivating glimpse into the heart of Tuscany’s renowned wine region.
Winding roads reveal a patchwork of lush, rolling hills dotted with ancient stone farmhouses and family-owned wineries. Visitors can admire the contrast of green vines and silvery olive trees, while enjoying breathtaking views of the surrounding countryside.
This picturesque journey showcases the quintessential Tuscan landscape, providing a tranquil respite from the bustling city.
Travelers will cherish the opportunity to witness the natural beauty that has inspired artists and winemakers for centuries.
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Tasting Chianti Wines: Classico, Reserve, and Tuscan Desserts

After marveling at the stunning Chianti countryside, guests can embark on a tasting journey to sample the region’s renowned wines.
The tour includes:
- Classico – the signature Chianti blend with notes of cherry and spice
- Reserve – fuller-bodied wines with increased complexity and aging
- Tuscan dessert wines – sweet, syrupy delights like Vin Santo, often paired with biscotti
Guests visit family-owned cellars to learn about the winemaking process and savor the unique flavors of each varietal.
The tasting experience provides an authentic glimpse into Chianti’s rich viticultural heritage and is a highlight of the day’s excursion.
Visiting Family Cellars, Olive Oil Producers, and Balsamic Vinegar Makers

As guests venture beyond the picturesque Chianti vineyards, they’re invited to enjoy the region’s rich culinary heritage by visiting family-owned olive oil producers and balsamic vinegar makers.
These intimate stops offer a rare glimpse into centuries-old traditions. Guests can witness firsthand the meticulous process of crafting premium extra virgin olive oil and aged balsamic vinegar.
They’ll learn about the local growing conditions, tasting notes, and artisanal techniques passed down through generations. These authentic experiences provide a deeper appreciation for Tuscany’s unparalleled food culture and the passion behind every local delicacy.
Dining Experiences: Local Restaurants and Family-Owned Vineyards

Guests on the Siena and Chianti Wineries Excursion have the opportunity to savor authentic Tuscan cuisine during their journey.
Lunch may be enjoyed at a local restaurant or family-owned vineyard, providing a true taste of the region. Options include:
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Dining at a traditional trattoria, where guests can indulge in regional specialties like pici pasta, wild boar ragu, and ribollita soup.
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Experiencing a leisurely lunch at a family-operated winery, complemented by their renowned Chianti wines.
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Savoring a farm-to-table meal showcasing locally sourced ingredients and the expertise of skilled Tuscan chefs.
These culinary highlights elevate the excursion, offering a memorable gastronomic experience.
Frequently Asked Questions
Are There Any Age Restrictions for This Tour?
This tour doesn’t have any age restrictions. It’s suitable for families and all ages can participate in the activities like wine tasting and visiting historic sites across Siena and Chianti.
Can We Customize the Itinerary to Include Specific Wineries?
Yes, the itinerary can be customized to include specific wineries. The tour operator is flexible and can accommodate requests for visiting particular family cellars, olive oil producers, or balsamic vinegar makers based on traveler preferences.
How Long Is the Drive Between Florence and Siena?
The drive between Florence and Siena is approximately 1 hour and 15 minutes, covering a distance of around 65 kilometers. The actual travel time may vary depending on traffic conditions and the specific route taken.
Do We Have Free Time to Explore Siena on Our Own?
The tour includes a guided walking tour of Siena’s historic center, allowing travelers to explore the city’s landmarks and boutiques. However, the itinerary does not provide dedicated free time for independent exploration of Siena.
Is There an Option to Extend the Tour Duration?
Yes, the tour can be extended to allow more free time in Siena. Travelers can request a longer duration when booking, providing more opportunity to explore the historic center and local shops at their own pace.
The Sum Up
This private tour offers a unique opportunity to take in the rich history, culture, and gastronomy of Siena and Chianti. Guests will explore Siena’s UNESCO-listed historic center, enjoy scenic drives through picturesque vineyards, and indulge in wine tastings and authentic Tuscan cuisine at family-owned wineries and trattorias. With complimentary hotel pickup and drop-off, it’s a seamless and unforgettable day for families seeking to experience the enchanting Siena and Chianti region.
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