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

A full-day private tour through Tuscany’s most charming towns, with wine, history, and authentic local flavor.
For $289.20 per person, you get around 7 hours of exploring Volterra and San Gimignano, with a private driver, hotel pickup, and drop-off included. This experience is perfect for those wanting a personalized glimpse into Tuscany’s medieval past, picturesque landscapes, and delicious wines—all at a comfortable, relaxed pace.

We particularly love the luxury of having a private driver, which lets you soak in the scenery without worrying about navigation or timing. The Tuscan farm lunch paired with multiple wine tastings offers an authentic taste of local food and drink, making this tour a true sensory journey.

One thing to consider is the time spent in each town—with just an hour in San Gimignano and a similar time in Volterra, you’ll want to be prepared for a brisk but comprehensive visit. Also, if you’re seeking guided commentary, note that the tour is driver-led; a guide can be arranged in advance if desired.

This tour suits travelers who appreciate historic towns, scenic drives, and good wine. It’s especially ideal for those who want flexibility, a private atmosphere, and the chance to enjoy Tuscan cuisine without the hassle of self-driving.

This experience made our article of Which Pisa Full-Day Tours To Choose? Our Best 3 Picks.

Key Points

• Private, flexible experience tailored to your pace.
• Includes a traditional Tuscan lunch and around five wine tastings.
• Visit historic sites like the Roman Theatre, Duomo, and medieval towers.
• Scenic drive through Chianti hills with views of vineyards and olive groves.
• Ideal for those wanting personalized attention without a large group.
• A taste of authentic Tuscan cuisine with olive oils, balsamic vinegar, and truffle oil tastings.

The Itinerary in Detail: What You Can Expect

Starting Point: A Comfortable Pickup and Scenic Drive

The journey begins with hotel pickup in an air-conditioned vehicle, making the start of the day smooth and hassle-free. Your driver—Massimiliano, as some reviews mention—becomes your informal guide, providing insights into the landscapes of Tuscany. The drive alone offers a chance to settle in and enjoy views of olive groves, vineyards, and sunflowers that define this region.

Stop 1: Exploring Volterra – A Medieval Treasure

We loved the way this town feels like stepping into a living postcard. The walled hilltop town of Volterra is packed with history, from its roots in the Etruscan civilization to its Roman ruins.

Highlights include:

• The Roman Theatre, a stunning remnant of antiquity, where you can imagine the crowds who once watched performances here.
• The octagonal Baptistery and the majestic Duomo, both showcasing architectural styles spanning centuries.
• The Palazzo dei Priori, Italy’s oldest town hall, with its impressive façade and interior.
• The Etruscan Arch, dating back to the 4th century BC, offers a tangible link to the past.

Expect about 1 hour and 30 minutes in this town. We found the free time balanced for wandering the streets, browsing artisan shops, or simply soaking up the views from the ramparts. One reviewer mentioned that the “tour made it easy to see everything without feeling rushed,” which suits a wide range of travelers—from history buffs to casual visitors.

Stop 2: Tuscan Farm Lunch and Wine Tasting at Podere La Marronaia

Next, we headed to a biodynamic farm for a real taste of Tuscany. The setting is idyllic—olive trees, cypress-lined drives, and rustic farm buildings. The lunch is a showcase of local ingredients: bruschettas, homemade pasta, cold cuts, Pecorino cheese, and more. It’s a hearty, authentic meal that gives you a sense of what locals enjoy daily.

What makes this stop stand out is the wine tasting—roughly five varieties including Chianti, Chianti Riserva, Vernaccia, and Super Tuscan—plus tastings of extra olive oils, balsamic vinegar, and truffle oil. Our reviewer Flemming highlighted that the “van and driver made this outstanding,” echoing the value of having a dedicated driver with no limit on wine samples.

The farm visit lasts about 1 hour and 30 minutes, giving plenty of time to savor each glass and learn about Tuscan wine-making techniques. The tasting experience is designed to pair with the food, creating a sensory harmony that’s both educational and delicious.

Scenic Drive Through Chianti Hills

Post-lunch, we meandered through the famous Chianti wine road, enjoying the soft curves of the hills dotted with vineyards, olive groves, and cypress trees. The scenery alone makes this part of the tour worth it, offering a taste of what makes Tuscany so visually stunning.

Stop 3: San Gimignano – The Town of Towers

The final stop is San Gimignano, known for its medieval skyline of over 70 towers, though only a handful remain today. We loved how walking through the narrow streets felt like turning back the clock.

Highlights include:

• The magnificent towers that are the town’s hallmark, offering panoramic views from above.
• The main square, perfect for a quick gelato—Gelateria Dondoli is famed for its ice cream, and locals swear it’s the best in the world.
• The town’s white wine, Vernaccia di San Gimignano, is a regional specialty, and you’ll likely get a chance to taste it.

You’ll have about an hour here, enough for a leisurely stroll, some photos, and a taste of local saffron or cured meats if you wish to explore more. One review mentions that the “town feels like an open-air museum,” which is a perfect way to describe it.

What Makes This Tour Stand Out?

This experience is designed for those who want a personalized, relaxed day without the constraints of a large group. The private vehicle and driver give you flexibility and comfort, allowing you to spend more or less time at each stop based on your interests. The lunch and wine tastings are thoughtfully included, making this a well-rounded day that combines history, scenery, and culinary delights.

Reviews highlight the knowledgeable driver and the quality of the wine and food, with Flemming praising the “outstanding” experience. The scenic drives through Chianti’s rolling hills** are just as memorable as the sites themselves, giving a true sense of Tuscany’s charm.

Price and Value

At nearly $290, this tour might seem a bit hefty, but considering private transportation, a substantial Tuscan lunch, and multiple wine tastings, it offers excellent value for travelers seeking a curated experience. It’s especially suited for those who prefer private outings over crowded group tours, wanting to savor the scenery and flavors without rushing.

Who Is This Tour Best For?

This tour appeals to history lovers eager to explore ancient towns, food and wine enthusiasts looking to enjoy authentic Tuscan flavors, and travelers desiring a flexible, private experience. It’s ideal for couples, small groups, or anyone who appreciates personalized attention and scenic drives. If your goal is a well-balanced day of sightseeing, tasting, and relaxing, this tour hits the mark.

FAQ

Is hotel pickup and drop-off included?
Yes, the tour begins with pickup from your hotel, B&B, or private flat, and ends with drop-off, making the day seamless.

How long is each stop?
You’ll spend about 1 hour and 30 minutes in Volterra, 1 hour and 30 minutes at the farm with lunch and wine tastings, and approximately 1 hour in San Gimignano.

Are guided tours available during the stops?
The tour is driver-led, meaning your driver provides commentary. If you desire a dedicated guide, you can request this in advance for an additional fee.

What is included in the meal?
A hearty Tuscan lunch featuring bruschettas, homemade pasta, cold cuts, Pecorino cheese, and more, paired with wine tastings.

How many wines are tasted?
You’ll sample around five local wines, including Chianti, Chianti Riserva, Vernaccia, and Super Tuscan.

Can I customize the experience?
Since it’s a private tour, flexibility is possible—discuss preferences with your driver in advance.

What should I wear or bring?
Comfortable shoes for walking, sun protection, and perhaps a small bottle of water. The tour provides bottled water, but extra is always welcome.

Is this tour suitable for children?
While mainly designed for adults, children who enjoy scenic drives and light sightseeing can enjoy the day; wine tastings are for adults only.

What is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund, making it a risk-free choice if your plans change.

To sum it up, this private Tuscany tour offers a thoughtfully curated day combining culture, landscape, and gastronomy. It’s perfect for those who want to avoid the crowds and enjoy a flexible, intimate experience with genuine local flavors. Whether you’re a history buff, a wine lover, or simply seeking a scenic escape, this tour delivers a well-rounded taste of Tuscany’s magic.