Volterra and San Gimignano: a taste of medieval Tuscany!

Travelers looking for a true slice of Italy’s enchanting past often find themselves overwhelmed by the options — but this private day trip to Volterra and San Gimignano offers a balanced mix of history, scenic beauty, and personalized attention. Designed for up to eight travelers, this nine-hour tour from Florence (or nearby cities like Pisa or Livorno) promises a relaxed, authentic exploration of two hidden gems off the typical tourist trail.

What we really love about this experience is its flexibility. Since it’s private, you’re in charge of how much time you spend at each stop — whether it’s wandering the cobbled streets of Volterra or marveling at the medieval towers of San Gimignano. Plus, the combination of comfort, local insights, and the chance to skip the crowds makes it a standout choice for those seeking a laid-back, immersive day in Tuscany. However, it’s worth considering that the price per group might seem steep for some, especially as food and wine tastings are optional extras rather than included. This tour is best suited for those who value personalized service and want a curated experience rather than a packed group tour.

Key Points

• Customized private experience means more time on what interests you most.
• Comfortable transportation with Wi-Fi keeps you connected and relaxed during the day.
• Two villages in one day provide a well-rounded glimpse into medieval Tuscany.
• Authentic sights like the Roman Amphitheater, Rossi Alabastri, and San Gimignano’s towers make the history come alive.
• Optional wine and food experiences offer a taste of local cuisine without the tour including it in the base price.
• Expert local guides add depth and personal stories that make the history vivid and memorable.

Exploring the Itinerary: What You Can Expect

The Roman Amphitheater: Stepping Into Ancient Rome

Your day starts with a quick stop at Anfiteatro Romano, an impressive piece of Roman engineering that still holds cultural significance today. Although the ticket isn’t included, we loved the quick panoramic view, which proved perfect for snapping photos of the amphitheater’s massive structure. As one reviewer noted, this site is still alive with music and events during summer, adding a layer of ongoing history. It’s a brief visit, but a great way to kickstart your immersion into Italy’s ancient past.

Rossi Alabastri Volterra: Craftsmanship and Tradition

Next, you’ll visit the Rossi Alabastri, a family-owned alabaster workshop that’s been around the longest in the region. Here, you get a free demonstration of alabaster craftsmanship, which is fascinating. The artisans’ skill is evident in the delicate carvings and luminous stones. Travelers have praised this stop for its authenticity and personal touch, with one reviewer mentioning how the demonstration was a highlight. It’s a quick visit, about 10 minutes, but one that offers insight into Tuscan craftsmanship and the region’s long-standing artisanal traditions.

Piazza dei Priori: Medieval Charm in Volterra

Strolling through Piazza dei Priori, you step into the heart of Volterra’s medieval vibrancy. The square features the Priory Palace and the tower seen in Twilight, adding a cinematic feel. The Cathedral opposite the square is also worth a quick look. This stop lasts about an hour, giving you enough time to soak in the atmosphere, snap photos, and maybe grab a gelato. Reviewers have expressed how practically empty the streets were during their visit, making it feel like you’re discovering a secret corner of Italy rather than a busy tourist spot.

Crossing the Chianti Countryside

From Volterra, you’ll drive through the Chianti region, famous for its wine, olive oil, and scenic vineyards. Here, the journey itself becomes part of the experience. If you choose, a lunch with wine tasting or just a wine tasting session can be arranged (food and drinks are extra). The hour and a half spent here is a wonderful transition from ancient cities to the lush, rolling hills of Tuscany. Travelers have remarked on how peaceful and picture-perfect the landscape is, with some saying it’s the kind of scenery that makes you want to stop the car and just stare.

San Gimignano: The Medieval Tower City

The final main stop is San Gimignano, a medieval town famous for its towers that create a skyline straight out of a fairy tale. You’ll have about an hour to explore the historic center — wandering the narrow streets, browsing artisan shops, and, of course, trying the best gelato in the main square. Many reviews highlight how stunning the town’s atmosphere is and how the towers seem to reach for the sky, making it a perfect spot for photos. Travelers also appreciate the chance to stroll freely and soak up the medieval vibe without feeling rushed.

What’s Included and What’s Not?

This tour provides several practical benefits, including air-conditioned vehicle, Wi-Fi, and bottled water—all valuable for a comfortable day out. The private transportation means you avoid the chaos of crowded group buses and can customize your itinerary slightly, within reason.

However, food, beverages (except water), museum entrance fees, and wine tastings are not included in the base price. We think this is fair, as it allows flexibility—you can opt for a simple tour or indulge in local wine and food experiences if you like. The price, around $1,021.75 for up to 8 people, reflects a high-quality, personalized service, which many reviewers feel is good value considering the private nature and expert guides.

Transportation and Timing

The 9-hour duration is well-balanced, giving enough time at each stop without feeling hurried. The use of air-conditioned vehicles with Wi-Fi means you stay comfortable and connected, and the private setup allows for spontaneous stops or extra time at places that pique your interest, as some guests have appreciated.

Guides and Personal Touch

Guests consistently praise the knowledgeable guides, particularly mentioning Giuliano, who many reviewers refer to as “fabulous” and “a wealth of information.” Their ability to share stories and insider tips elevates the experience beyond just sightseeing.

Who Would Love This Tour?

If you’re someone who appreciates a personal touch, loves exploring historic sites without the crowds, and enjoys scenic drives through Tuscany’s famed countryside, this private tour is a stellar choice. It’s perfect for couples, families, or small groups of friends who want a relaxed, curated experience with flexible timing.

While the price may seem high, the combination of private transportation, personalized service, and access to lesser-known sites offers excellent value for those wanting a deeper, more authentic taste of Tuscany. The optional wine and food tastings also mean you can tailor the experience to your culinary interests, making each trip uniquely yours.

The Sum Up

This Volterra and San Gimignano tour delivers a genuine, immersive experience into Tuscany’s medieval and ancient past. Its private setup, comfortable transport, and knowledgeable guides create a seamless journey that feels both special and authentic. The stops at Roman ruins, artisan workshops, medieval squares, and vineyard-lined hills provide a well-rounded glimpse of the region’s culture and scenery.

It’s an ideal choice for travelers who value personalized attention, flexibility, and the chance to explore off-the-beaten-path gems without the rush of larger group tours. The inclusion of iconic sites, stunning vistas, and local artisan experiences makes it more than just a sightseeing day—it’s a curated journey into Tuscany’s soul.

For those seeking a relaxing, enriching day in Italy’s heartland, this tour offers excellent value, memorable moments, and a genuine taste of what makes Tuscany so captivating.

FAQ

Is this tour suitable for all ages?
Yes, most travelers can participate, and it’s especially good for those who prefer a private, relaxed experience. Service animals are allowed, and the pace can be adjusted slightly.

How long do we spend at each stop?
You’ll have around 10 minutes at the Roman Amphitheater and Rossi Alabastri, about an hour in Volterra, one and a half hours crossing the Chianti countryside, and an hour in San Gimignano. The timing offers a good balance between seeing sights and enjoying the atmosphere.

Are meals included in the tour?
No, meals are not included in the base price. However, you can arrange a lunch with wine tasting, which is an optional addition, and food and drinks outside water are at your expense.

What is the transportation like?
You’ll travel in a private, air-conditioned vehicle equipped with Wi-Fi, ensuring comfort and connectivity during your day.

Can I customize the itinerary?
While the core stops are fixed, the private nature of the tour allows some flexibility—discuss your preferences with your guide to make the most of your day.

How far in advance should I book?
On average, this tour is booked 73 days ahead, which is advisable if you want to secure your preferred date, especially in peak seasons.

This tour offers a fantastic, personalized way to experience the medieval charm of Tuscany’s lesser-known towns, with the convenience and comfort that make a day away from the crowds truly worthwhile.