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Discover Tuscany’s medieval charm on a private tour from Florence, featuring San Gimignano, Volterra, and scenic countryside with a knowledgeable driver.

If you’re visiting Florence and craving a true taste of Tuscany’s timeless allure, the San Gimignano and Volterra Tour by Private Luxury Van offers an inviting glimpse into the region’s art, history, and local craftsmanship. This 8-hour journey combines the charm of medieval towns with scenic countryside views, all while riding comfortably in a private vehicle with your own dedicated driver.
What we really love about this experience is its flexibility and personal touch. Having a private driver means you can set your own pace and focus on what interests you most—whether that’s exploring ancient ruins, sampling local wines, or browsing artisanal shops. Plus, the van is cozy and upscale, making the trip both relaxing and stylish.
One consideration worth noting is the price point—at $868.20 per group (up to 7), it’s an investment. For some, this may seem high compared to group tours, but the personalized service and exclusive access to sights make it worth the expense. This tour is ideal for travelers who value comfort, authentic experiences, and the ability to customize their day.
This private tour suits those looking for a luxurious, less hurried way to discover rural Tuscany, especially couples, small groups, or families eager for a tailored adventure rather than a large, crowded bus.

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The tour kicks off at your Florence hotel around 9:30 am, with a private driver ready to whisk you away in a sleek, well-maintained van. From the start, the journey feels exclusive—no crowded buses or rigid schedules. The drive lasts about an hour, during which your driver shares insights into the Tuscan landscape, giving a preview of the charming towns to come.
Your first destination is Volterra, a city bursting with history. Known for its Etruscan roots, Roman amphitheater, and medieval architecture, Volterra offers a rich tapestry of past civilizations. The highlight here is the Cattedrale di Santa Maria Assunta, where you can admire stunning frescoes and intricate stonework. Reviewers mention the Etruscan tombs and Roman baths, which reveal the city’s ancient origins—some built hundreds of years before Christ.
A walk past the Palazzo dei Priori provides a glimpse into medieval governance, while local alabaster workshops give you a chance to see artisans at work. One traveler noted the alabaster trade is a long-standing tradition, and some workshops still produce beautiful sculptures and jewelry today.
A key perk of this tour is the option to include a lunch at a local farm, like Fattoria San Donato. While not included in the price, this is a fantastic opportunity to sample wines and organic products directly from the source. Many visitors find this farm visit a highlight, appreciating the chance to taste authentic Tuscan flavors in a peaceful rural setting.
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After exploring Volterra, your driver takes you to San Gimignano, often called the “Medieval Manhattan” because of its iconic towers. Inside the UNESCO World Heritage site, you’ll have ample free time to wander the narrow, cobblestone streets, soak up the atmosphere, and snap photos of the skyline.
The Piazza Duomo serves as a focal point, with the Collegiate Church displaying frescoes and impressive stonework. Climbing to the town’s highest point offers sweeping views of the surrounding vineyards and countryside—a perfect spot for photos. Don’t miss the Piazza della Cisterna, a sunny square lined with cafes and artisan shops, where you can relax and observe local life.
Reviewers love that they can choose where to eat—some opt for authentic trattorias, while others indulge in gelato recommended by the driver. One reviewer called San Gimignano a “dive into the Middle Ages,” emphasizing its well-preserved towers and lively streets.
Returning to Volterra, you’ll have the chance to browse boutiques and workshops, especially those specializing in alabaster artwork. Reviewers consistently praise the quality and beauty of the craftsmanship, often mentioning how it’s a great place to pick up unique souvenirs.
As the day winds down, your driver takes you back to Florence, sharing more insights into the Tuscan landscape. The comfortably-paced, private nature of the tour means you can sit back and reflect on a day filled with history, art, and scenic beauty—without the rush of larger group tours.


Kevin R. praised the “great tour with Massimo,” highlighting his knowledge and time spent showing around. Donna M. appreciated the less crowded, more authentic feel of the area, emphasizing her ability to split time between the towns. Both reviews highlight the personalized attention and scenic beauty that make this trip special.

This private tour offers a balanced combination of cultural sightseeing, scenic countryside, and authentic local experiences—all tailored to your pace. The knowledgeable driver, who doubles as a local guide, enriches the journey with fascinating insights into Tuscan history and traditions. With fewer crowds and the freedom to explore at your leisure, it’s ideal for travelers seeking a luxurious, relaxed day out of Florence.
While the price tag might seem steep, the personalized service, comfort, and exclusive access make it a worthwhile choice for those who want a more intimate, customizable Tuscan adventure. Whether you’re a history buff, art lover, or simply looking to enjoy the stunning scenery, this tour delivers a well-rounded, memorable experience.
If you prefer guided tours with large groups, or are on a tight budget, other options might suit you better. But for a private, tailored exploration of Tuscany’s medieval gems, this tour from Chianti Drivers is a compelling option.

Is hotel pickup included? Yes, the tour offers hotel pickup and drop-off in Florence, making the experience seamless.
How many people can join this tour? Up to 7 guests per booking, ideal for small groups or families.
What is the duration of the tour? Approximately 8 hours, giving ample time to explore both towns and enjoy the countryside.
Can I customize the itinerary? While the tour is set to visit San Gimignano and Volterra, you can choose to spend more or less time at each stop, and optional farm lunch arrangements are available.
What is the price per group? $868.20, which covers up to 7 people, making it a good value for a private experience.
Do I need to book in advance? Yes, most travelers book about 50 days ahead to secure their spot.
Is there a guide with me during the tour? No professional city guide is included, but your driver shares rich insights, making it a personalized guided experience.
Are meals included? No, but an optional farm lunch with wines and organic products can be organized.
What should I bring? Comfortable shoes for walking, a camera, and some cash for optional purchases or meals.
To sum it up, if you’re after a luxurious, flexible, and authentic way to experience Tuscany’s medieval towns and scenic countryside, this private tour ticks all the boxes. It’s perfect for travelers who value comfort, personalized attention, and a deeper connection with local culture and history.