PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience

Experience the Best of Tuscan Hill Towns with a Private Full-Day Tour to Volterra and San Gimignano

Thinking about visiting some of Italy’s most picturesque hill towns without the hassle of public transport or guided crowds? This private full-day tour offers a relaxed way to explore two enchanting spots—Volterra and San Gimignano—while enjoying a delicious Tuscan lunch and wine tasting. With seamless pickup, flexible free time, and the comfort of private transportation, it’s an experience tailored for travelers who want to soak in the scenery and history at their own pace.

What we really like about this trip? First, the personalized service makes all the difference—your own driver and the freedom to explore without feeling rushed. Second, the wine tasting experience at a family-run Chianti farm offers an authentic taste of Tuscany that you won’t forget. One thing to keep in mind? The tour is quite comprehensive, so it’s best suited for those who want a full-day immersion rather than a quick visit. Overall, if you’re after a well-rounded, relaxed day combining culture, scenery, and good food, this tour could be a great fit.

Key Points

• Hassle-free private transport saves time and eliminates the stress of navigating public transit or busy tour groups.
• Flexible exploring allows you to wander freely in Volterra and San Gimignano, with free time to soak in the atmosphere.
• Authentic Tuscan lunch at a biodynamic winery features a variety of local dishes paired with five different wines.
• Scenic drive through Chianti’s famous wine road offers stunning views of rolling hills, vineyards, and olive groves.
• Rich historical stops including Roman theaters, medieval towers, and notable landmarks in both towns.
• Highly rated guides and drivers help make your experience enjoyable, friendly, and informative.

An In-Depth Look at the Itinerary

Starting Point: Comfort and Convenience

Your day begins with a pickup around 8:30 am, with air-conditioned vehicle transport that’s private, meaning you won’t be crammed into a large group. The driver is described as friendly and knowledgeable, which really helps set a relaxed tone for the day. These details matter because they make the entire experience feel more personal and less rushed.

Stop 1: Discovering Volterra

Your first stop is the charming Etruscan hill town of Volterra. Known for its ancient roots and stunning architecture, you’ll have time to explore its narrow streets at your own pace. Highlights include the Roman Theater, the octagonal Baptistery, the Palazzo dei Priori, and the Etruscan Arch dating back to the 4th century BC.

According to reviews, travelers appreciated that they could wander freely, with one commenting that the guide was friendly and stopped at a lookout as a bonus. This flexibility means you can linger around the main sights or take in some quiet moments soaking in the views. The self-guided approach is ideal for those who want to absorb the atmosphere without a heavy schedule.

Stop 2: Tuscan Lunch and Wine Tasting at Podere La Marronaia- Le Colonne

After exploring Volterra, you’ll head to a typical family-run organic farm in Chianti. Here, lunch is more than just a meal—it’s an experience. Expect delicious local dishes like bruschetta, lasagna, homemade pasta, cured meats, pecorino cheese, and a sweet dessert.

During this time, you can indulge in five wine tastings—including Chianti, Chianti Riserva, Sangiovese, Vernaccia, and even a Super Tuscan or Rosé. Plus, there’s a variety of tastings of extra virgin olive oils, balsamic vinegar, truffle oil, and pepper olive oil, helping you understand how Tuscan flavors come together. Reviewers described the lunch as “great,” emphasizing how well the wines and food paired, and how the experience felt authentic and connected to local traditions.

Scenic Drive Through Chianti and Siena Hills

Post-lunch, the route takes you along the famous “Chianti wine road”, offering panoramic views of cypress-lined roads, vineyards, and olive groves. This drive alone is a treat if you love scenic landscapes and want to see the quintessential Tuscan countryside.

Final Stop: San Gimignano

Your last stop is the medieval town of San Gimignano, famed for its iconic towers. Once boasting over 70 towers during the Middle Ages, today you’ll see around a dozen that give the town its distinctive skyline. The self-guided visit lasts about an hour, giving you time to stroll through the medieval streets, admire the white Vernaccia wine, and perhaps sample the “best gelato in the world” as some reviews suggest.

Travelers praised the free time here, noting that the town feels like stepping back into the Middle Ages. The walk up to the towers offers spectacular views over the Tuscan hills, making it a perfect photo opportunity.

What Makes This Tour Stand Out

This experience balances guided elements with free exploration, which many travelers find appealing. The private transport ensures a relaxed pace and the flexibility to customize your time in each town. The lunch at the winery offers genuine insight into Tuscan cuisine and wine-making, making it more than just a sightseeing trip—it’s a taste of local life.

The high ratings (5.0 from 4 reviews) speak to consistent satisfaction, especially praising the friendly guides, beautiful scenery, and excellent wine and food. One reviewer even called the family winery experience “top notch” and felt like they were part of the family.

However, keep in mind that this is a full-day experience—about 7 hours—so it suits those who enjoy a comprehensive, relaxed tour rather than quick visits. It also involves some walking and self-guided exploration, which should be manageable for most travelers.

The Cost and Its Value

At around $289 per person, the price covers private transportation, lunch, wine tastings, and the guided drives. Given the inclusions—especially the personalized service and authentic experiences—many find this offers good value for a curated, hassle-free day. You’re essentially paying for convenience, quality, and a chance to see two of Tuscany’s most captivating towns in one go.

Who This Tour Is Perfect For

Travelers who want a hassle-free day exploring Tuscany’s hill towns without the crowds or public transit worries. It’s ideal if you value personalized service, authentic food and wine experiences, and the flexibility to wander at your own pace. If you’re traveling as a couple, a small group, or even a small family, this tour offers a cozy, well-rounded way to enjoy the Tuscan countryside.

FAQs

Is this a guided tour?
It’s a private tour, so only your group participates. The driver is friendly and knowledgeable, but it’s more about private transport and free exploration rather than a guided walk.

What’s included in the price?
The tour covers private air-conditioned transportation, bottled water, lunch at a winery with wine tastings, and various tastings including extra olive oil, balsamic vinegar, and truffle oil.

Can I customize my time in each town?
Yes, the tour offers free time in both Volterra and San Gimignano, allowing you to explore according to your interests.

How long is the drive?
The exact duration isn’t specified, but the entire tour lasts about 7 hours, with a scenic, relaxed drive through the Tuscan countryside.

Is there a minimum or maximum group size?
As a private tour, it’s booked exclusively for your group, ensuring a more intimate experience.

What should I wear or bring?
Comfortable shoes for walking, sun protection, and a camera are recommended to enjoy the sightseeing and scenic views.

What about children or families?
While not specifically targeted at families, the relaxed pace and flexible exploration options make it suitable for most travelers, including those with children.

Are there any restrictions or considerations?
Most travelers can participate, but it’s a full-day trip, so be prepared for some walking and a long day out.

Is it possible to cancel?
Yes, the tour offers free cancellation if canceled at least 24 hours in advance, giving some peace of mind.

To sum it up, this private tour offers a well-balanced, relaxed way to experience Tuscany’s highlights—without sacrificing authenticity or comfort. It’s perfect for those who want a meaningful day of sightseeing, good food, and wine, all tailored to their pace. If you love scenic drives, medieval towns, and genuine Tuscan flavors, this could be your ideal day trip.