Volterra and San Gimignano: a taste of medieval Tuscany!

Planning a trip to Florence and craving a deeper dive into Tuscany’s less crowded gems? This private tour to Volterra and San Gimignano offers a personalized journey through two of Italy’s most captivating medieval villages. With a focus on authentic experiences, knowledgeable guides, and scenic countryside, it promises a full day of cultural richness and beautiful vistas.

What we love most about this experience is the flexibility—since it’s a private tour, your group can spend more time exploring what interests you most. Plus, the chance to visit off-the-beaten-path spots like the Roman Amphitheatre and Rossi Alabastri Volterra adds a layer of authenticity that large group tours often miss.

One thing to consider is the price—at over $1,000 for up to 8 people, this is a premium experience. However, when you factor in private transportation, Wi-Fi on board, and tailored itineraries, it’s a solid value for those wanting a curated, stress-free day.

This tour suits travelers who appreciate history, scenic drives, and a personalized approach—perfect for couples, families, or small groups seeking a relaxed, immersive taste of Tuscany beyond the usual crowded spots.

Key Points

• Private and customizable experience tailored to your interests
• Comfortable transportation with Wi-Fi and bottled water included
• Visit less touristy sites like the Roman Amphitheatre and Rossi Alabastri Volterra
• Explore two iconic medieval villages in one day—Volterra and San Gimignano
• Optional wine tastings and local food experiences available (not included in the tour price)
• Ideal for small groups seeking an exclusive, flexible adventure with a knowledgeable guide

An Overview of the Experience

This tour is designed for those who want to uncover Tuscany’s medieval charm without the crowds. It lasts roughly 9 hours, and the flexible, private nature of the trip makes it a perfect choice for those looking to customize their day. From the moment you’re picked up in Florence (or other nearby cities), the journey begins in comfort, with air conditioning and Wi-Fi to keep things convenient and connected.

The core appeal lies in the blend of history, scenery, and authentic local flavor. Unlike many group tours, this is tailored to your pace, allowing you to linger longer at favorite spots or skip over ones you’re less interested in.

The Itinerary, Step by Step

Stop 1: The Roman Amphitheatre in Volterra

Our journey kicks off with a quick visit to the Roman Amphitheatre, an ancient relic with ongoing cultural relevance. You’ll get a peek at this historic site from a panoramic viewpoint, perfect for photos. While admission isn’t included, the view alone makes it worth a few moments. The amphitheatre is still used today for summer concerts and events, which adds a lively touch to an ancient site. Expect to spend around 10 minutes here, enough for a quick photo and a sense of Roman ingenuity.

Stop 2: Rossi Alabastri Volterra

Next, you’ll visit Rossi Alabastri Volterra, a company with over a century of tradition in alabaster craftsmanship. The free demonstration at their workshop showcases the skill and artistry that have kept this craft alive. This stop offers a genuine glimpse into local artisanal work, making it far more authentic than a typical museum visit. Reviewers love how this visit is a short but insightful window into Italy’s centuries-old craftsmanship, with many appreciating the opportunity to see the process firsthand.

Stop 3: Piazza dei Priori in Volterra

From there, you’ll explore the historic center of Volterra, centered around the Piazza dei Priori. Here, the Priory Palace and the iconic tower, famously featured in the film Twilight, are sights you won’t forget. With about an hour to wander, you can soak in the medieval atmosphere, snap photos, and appreciate the architecture. The cathedral nearby offers a peaceful backdrop and a chance to see the religious art and history that permeates this town.

Stop 4: The Chianti Countryside

Driving across the Chianti region offers a scenic respite, where rolling hills, vineyards, and olive groves dominate the landscape. This part of the tour is a favorite among reviewers, who rave about the stunning views and the chance to breathe in the quintessential Tuscan scenery. You might choose to add a lunch with wine tasting or just enjoy a tasting session without food (both optional, and not included in the price). The drive itself, approximately 1.5 hours, is a highlight, giving you a chance to relax and take in the lush landscape.

Stop 5: San Gimignano

Finally, you arrive in San Gimignano, the “medieval Manhattan,” known for its impressive towers and preserved walls. The town’s atmosphere is magical—narrow cobblestone streets, lively squares, and views over the Tuscan countryside. You’ll spend about an hour here, and most visitors agree that the gelato in the main square is an absolute must-try. Many reviews mention how enchanting the town feels, especially when lit up in the late afternoon.

What’s Included and What’s Not?

Included in the price are:
– Air-conditioned vehicle with Wi-Fi and bottled water
– Private transportation, ensuring flexibility and comfort
– The ability to tailor your experience

Not included are:
– Lunch, which can be arranged optionally
– Entry fees for certain sites, while most stops are free or have optional paid entrances
– Beverages beyond water, wine tastings, and gratuities

The value here is in the personalized service and convenience—you get to avoid crowded tours and stick to what interests you most.

Authentic Reviews and Insights

Travelers consistently praise the knowledgeable guides who make the history come alive. For instance, one reviewer mentioned that their guide, Giuliano, was “very kind” and kept everyone entertained, which shows how a good guide can elevate the experience. Multiple reviewers highlight the stunning views and the value of exploring lesser-known sites like Rossi Alabastri, rather than just the typical tourist spots.

The food and wine element is a bonus. While not included, many travelers appreciate the option to include a lunch at a local farm or winery, which can turn a sightseeing day into a full Tuscan culinary experience. The scenic drive through Chianti also gets glowing reviews, often described as an “escape into a postcard.”

Why This Tour Works for You

This isn’t your average day trip. If you enjoy history, beautiful landscapes, and personalized service, this tour hits the mark. It’s especially great for small groups who want a more intimate, flexible experience—whether you’re traveling with family, friends, or a partner. The comfort of private transportation means you can relax and truly savor the scenery without feeling rushed or crowded.

If you’re keen on authentic local craftsmanship and want to avoid the commercialized feel of larger tours, the stops at Rossi Alabastri and the less touristy sections of Volterra are a real plus.

However, be mindful of the price point—this is a premium experience, but many feel that the quality of guides, the flexibility, and the scenic stops justify the cost. It’s ideal if you’re looking for a luxury, personalized day in Tuscany that offers a taste of genuine, lived-in Italy.

The Sum Up

For travelers seeking a relaxed, customizable, and authentic way to explore Tuscany’s medieval towns, this private tour delivers. It combines stunning scenery, local craftsmanship, and historic charm in a way that large group trips simply can’t match. The insider insights from reviewers highlight the importance of a knowledgeable guide and the value of visiting less touristy sites, making it a worthwhile choice for those who want more than just the surface.

While the price might be on the higher side, the private transportation, flexible itinerary, and exclusive visits offer tangible value. It’s an excellent option for small groups or couples wanting a more intimate, tailored experience that captures the essence of Tuscany’s medieval heartlands.

If you’re a lover of history, scenic drives, and authentic local encounters, this tour is likely to be one of the highlights of your trip to Italy.

FAQ

Is this tour suitable for all ages?
Yes, most travelers can participate, and the private setting makes it accommodating for families, couples, or small groups.

How long is the drive between the stops?
The drive across the Chianti countryside lasts about 1.5 hours, providing ample time to relax and enjoy the scenery.

Can I customize the itinerary?
Since it’s a private tour, yes—you can discuss your interests with your guide and tailor the experience accordingly.

Are food and wine tastings included?
No, these are optional extras. You can arrange a lunch or wine tasting at an additional cost, but they are not included in the base price.

Is parking available at the sites?
Most sites like Volterra and San Gimignano are accessible by car, and private transportation is included, so parking logistics are managed smoothly.

What should I wear?
Comfortable shoes are recommended, especially for walking through cobblestone streets and historic sites. Dress appropriately for the weather.

Are admission fees included?
Most stops are free or have optional paid entrances. The Roman Amphitheatre’s entrance isn’t included, but the views are accessible from outside.

Is this tour available year-round?
Yes, but note that the tour requires good weather, and cancellations for poor weather are fully refundable or can be rescheduled.

This private tour to Volterra and San Gimignano offers an authentic, intimate look at some of Tuscany’s most cherished medieval towns, with the flexibility and comfort that make it stand out. It’s perfect for travelers who want a curated experience, away from crowds, and eager to discover the region’s genuine magic.