Volterra and San Gimignano: a taste of medieval Tuscany!

A Private Day in Medieval Tuscany: Visiting Volterra and San Gimignano

If you’re seeking a slice of authentic Tuscany that avoids the crowds and dives into history, this private tour offers just that. For around $1,022 per group (up to 8 people), you get a full day exploring Volterra and San Gimignano, two towns brimming with medieval charm, local craftsmanship, and striking views. Led by a knowledgeable guide, you’ll enjoy the comfort of an air-conditioned vehicle with Wi-Fi, making every moment relaxing and informative.

What we love most? First, the ability to customize your time in each location—whether you want a quick photo, a taste of local alabaster craftsmanship, or a leisurely walk through the historic streets. Second, the chance to experience these places in a private setting, far from the bus crowds and rushed schedules.

However, keep in mind that the tour involves some driving through scenic countryside, which means a taste of Tuscany’s real landscape, but it also might be a long day if you’re not a fan of road trips. This tour is ideal for travelers who prefer a flexible, personalized experience and who appreciate a combination of history, scenery, and local culture.

If you enjoy discovering lesser-known historic sites, want to avoid large tour groups, and love a good mix of scenic drives and cultural stops, this tour is likely a perfect fit.

Key Points

• Private Experience: The tour is exclusive to your group, allowing flexibility and personalized attention.
• Historical and Cultural Sights: Visit a Roman amphitheater, alabaster workshops, and medieval town squares.
• Scenic Drive: Enjoy a drive through the famous Chianti countryside, with optional wine tasting.
• Comfort and Convenience: Ride in an air-conditioned vehicle with Wi-Fi, with pickup options from Florence.
• Authentic Towns: Explore less touristy, authentic towns with genuine charm and fewer crowds.
• Flexible Duration: The day runs approximately 9 hours, with enough time to soak in each site without feeling rushed.

Discovering the Heart of Medieval Tuscany

This tour combines the best of both worlds—history and scenery—making it a well-rounded day trip for those wanting to experience real Tuscany beyond the typical tourist spots. From the start, your driver will meet you in Florence, Livorno, or Pisa, providing a hassle-free pickup. The journey begins with a quick glimpse of the Roman Amphitheater in Volterra, an ancient relic where you can imagine locals enjoying summer concerts amid ruins that have stood for centuries.

Exploring Volterra’s Historical Roots

Within minutes of arrival, you’ll be at the Anfiteatro Romano, a site that still hosts summer events. The nearby panoramic viewpoint offers a perfect spot for photographs—ideal for capturing the ancient stones and sweeping Tuscan hills in the background. While admission isn’t included, the quick stop allows you to appreciate the scale and significance of Roman influence in this hilltop town.

Next, a visit to the Rossi Alabastri Volterra offers a peek into alabaster craftsmanship, a centuries-old tradition. The company’s lab hosts a free demonstration of artisans shaping this soft stone, giving you an authentic look at local craftwork. As one review noted, “We did a brief tour of the Rossi Alabastri, and it was a highlight for us—the craftsmanship and history behind alabaster are fascinating.”

From here, you’ll stroll through Piazza dei Priori, the bustling heart of Volterra. The square is framed by the Priory Palace and the Torre dei Priori, both they say, are recognizable from the Twilight movies. The cathedral on the square adds to the medieval charm, and most visitors spend about an hour wandering its streets, browsing shops, or sitting at a cafe.

The Drive through Tuscany’s Heartland

After soaking in Volterra, the tour continues with a scenic drive across the Chianti countryside. This area—often confused with the entire region of Tuscany—actually refers specifically to the land of wine and olive oil. The landscape is dotted with vineyards, cypress-lined roads, and rustic farmhouses. While food and drinks aren’t included, the scenery alone justifies the drive. If you want, a lunch with wine tasting can be arranged, offering a taste of local produce and tradition.

San Gimignano: A Tower-Laden Town

Your next stop is San Gimignano, the so-called “Medieval Manhattan,” famous for its skyline of medieval towers. Here, you’ll have about an hour to explore the historic center, walk among the towers, and enjoy the lively atmosphere. Don’t miss the chance to try the famous gelato in the main square—a sweet reward after wandering the narrow streets. Several reviews highlight this charming town as “fabulous,” with visitors praising the “beautiful atmosphere” and “great photo opportunities.”

What’s Included and What’s Not

This tour covers your private transportation, Wi-Fi, and bottled water—making the day comfortable and convenient. You’ll be in a small, private group with the flexibility to tailor your stops, which many reviewers find invaluable. Food, beverages (besides water), museum entrance fees, and wine tastings are not included but can be arranged separately.

The Value of the Tour

Given the personalized approach and the inclusion of transport, this tour offers excellent value, especially considering the cost per group rather than per person. The reviews attest to the value: “Our guide was very kind and made our trip so enjoyable,” and “We practically had the towns to ourselves,” both of which enhance the experience.

Authentic Experiences and Honest Observations

Several travelers mention how the guides made the trip special. Giuliano, one reviewer noted, “shared a wealth of information,” making history come alive. The small group size ensures you’re not just another face in a crowd, allowing for questions and tailored experiences.

The scenic drive through Chianti is a highlight, providing rolling hills and timeless landscapes that are best appreciated in person. The towns themselves are a delight—full of historic architecture, lively squares, and artisan shops. The alabaster workshop demonstrates genuine craftsmanship, a rare opportunity to see local traditions in action.

Considerations

While this tour offers flexibility, it is still a full day—about 9 hours—so it’s best suited for travelers who enjoy sightseeing at a relaxed but steady pace. If you’re looking for a more intensive wine tasting experience or want to include meals, you’ll need to make arrangements outside the initial fee.

Who Should Book This Tour?

This is an ideal choice for history buffs wanting to see authentic medieval towns, couples or families seeking a personalized experience, and travelers who appreciate scenic drives and local craftsmanship. If you’re looking for a luxury, all-included experience, this might not be the best fit, but if you value flexibility, intimacy, and genuine culture, you’ll find this tour rewarding.

Final Thoughts

This private tour of Volterra and San Gimignano delivers a well-balanced mix of history, scenery, and artisan craftwork. The flexibility to customize your visit, combined with a knowledgeable guide and comfortable vehicle, makes it stand out. It scores highly on reviews for friendly guides, stunning views, and authentic experiences—all essential ingredients for a memorable Tuscan day.

While it’s a longer day and doesn’t include meals or museum entries, the overall experience offers great value, especially for those eager to explore beyond the typical tourist routes. It’s perfect for anyone wanting a personalized, relaxed way to experience the medieval heart of Tuscany.

FAQs

Is this tour suitable for all ages?
Yes, most travelers can participate, and the private setup makes it flexible for families, couples, or groups of friends.

How long does each stop last?
Typically, the stops vary from about 10 minutes at the Roman Amphitheater and alabaster workshop to approximately an hour in each town, giving enough time to see key sites and take photos.

What’s included in the price?
Your group gets private transportation, an air-conditioned vehicle with Wi-Fi, bottled water, and a flexible schedule. Food, drinks besides water, museum fees, and tastings are extra.

Can I arrange a wine tasting or lunch?
Yes, there’s an option to include a wine tasting or a meal at a local farm, but these are not included in the base price. You can coordinate this with your guide.

How far in advance should I book?
On average, this tour is booked 73 days ahead, so planning early ensures availability.

What if the weather is bad?
The tour requires good weather; if canceled due to rain or bad conditions, you’ll be offered a different date or a full refund.

This private tour of medieval Tuscany offers a thoughtful, intimate way to experience the region’s history, scenery, and craftsmanship. Perfect for travelers seeking a genuine, customizable day away from crowds, it promises authentic moments and lifetime memories.