Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience Tuscany on a private day trip from Florence to Volterra and San Gimignano, including lunch, wine tastings, and personalized sightseeing in 7 hours.

This private tour offers a full taste of Tuscany with visits to Volterra and San Gimignano, two iconic hill towns. For $231.52 per person, you’ll spend approximately 7 hours exploring these historic sites, enjoying a Tuscan lunch with wine tasting, and traveling in a comfortable, air-conditioned vehicle. The tour includes pickup from your Florence accommodation and a private driver, making it a relaxed and personalized experience.
While the tour is perfect for those seeking an intimate and flexible approach to sightseeing, it’s worth noting that a full guide is not included, although it can be requested in advance for an additional fee. The group is small and private, ensuring a tailored experience. The average booking window of 31 days reflects its popularity among visitors eager to explore Tuscany’s countryside and medieval towns with ease.

If wine interests you, we've examined these other wine experiences in Florence

The tour begins with a pick-up at your Florence hotel, B&B, or private flat, setting the tone for a relaxed, stress-free day. The driver takes you through the rolling hills of Tuscany, passing olive groves, vineyards, and sunflower fields. This scenic ride offers an immediate glimpse of how picturesque and tranquil the Tuscan landscape is.
The journey itself becomes part of the adventure, with the driver sharing brief insights into the region’s geography and cultural landscape. This is a perfect way to ease into the day and get into the spirit of Tuscany’s natural beauty before arriving at your first stop.
Volterra welcomes visitors with its walled medieval architecture built atop a hill. The town is a reminder of Italy’s Etruscan roots, with some of the original Etruscan gates still standing, and a museum packed with Etruscan and Roman relics.
Key sights include the Roman Theater, which dates from ancient times, and the octagonal Baptistery and Duomo, which showcase the town’s religious architecture. The visit is self-guided, giving you the freedom to explore at your own pace. With around 90 minutes allocated, you can take your time to stroll through charming streets, browse local shops, or simply enjoy the panoramic views from the hilltop.

After exploring Volterra, the tour heads to a family-run organic farm, Podere La Marronaia- Le Colonne, for a genuine Tuscan lunch. The lunch features bruschetta, lasagna, or homemade pasta, along with cured meats, pecorino cheese, and dessert.
This farm offers an insider look at Tuscan cuisine, with a tasting of five wines, including Chianti, Chianti Riserva, Sangiovese, Vernaccia, and Brunello. Visitors also sample extra virgin olive oils, balsamic vinegar, and truffle oil, making this a true culinary highlight. The two-hour sitting delivers a delicious meal paired with expert wine tastings, showcasing the region’s best produce and winemaking traditions.

Post-lunch, the drive continues along the famous Chianti wine road, winding through the hillsides dotted with cypress trees, olive groves, and vineyards. This scenic route offers stunning views characteristic of the Chianti region, with many opportunities for photos and short stops.
The drive culminates in the medieval town of San Gimignano, renowned for its towers and preserved architecture. The journey itself emphasizes the region’s natural beauty and the classic Tuscan landscape, making the transition to the town even more captivating.
Keen to taste more of Florence? We've looked into these other food and drink experiences

Known as the “Town of Fine Towers,” San Gimignano once boasted over 70 towers during the Middle Ages. Today, about 14 of these remain, giving the town its distinctive skyline that looks like a fairy-tale settlement.
The self-guided visit lasts about an hour, allowing plenty of time to wander through narrow cobblestone streets, visit local artisan shops, and enjoy the views of the surrounding countryside. The main square offers a chance to taste the world-famous Vernaccia di San Gimignano, a crisp white wine made from local grapes.
A highlight is sampling the famous ice cream in the world, which local shops proudly serve in the main square—a sweet note to conclude your visit.

This private tour ensures a smooth experience with air-conditioned transportation and bottled water provided throughout the day. The driver is a local expert, making the classic Tuscany scenery more engaging with brief commentary.
The start time is set at 9:00 am, and the itinerary offers a flexible yet well-paced schedule, with self-guided exploration at each stop. The pickup service means no need to worry about parking or navigating, especially helpful for visitors unfamiliar with the region.

The lunch and wine tasting component stands out as a genuine highlight. The 5 wine tastings include Chianti, Chianti Riserva, Sangiovese, Vernaccia, and Brunello. These wines are paired with Tuscan delicacies, emphasizing local produce and traditional winemaking techniques.
Along With wines, you sample extra olive oils, balsamic vinegar, and truffle oil, elevating the meal into a comprehensive taste of Tuscany’s culinary craftsmanship. The experience is informal yet educational, perfect for those interested in regional flavors.
Both Volterra and San Gimignano are free to enter, allowing visitors to spend their time exploring without entrance fees. The self-guided approach gives flexibility to linger or move quickly, depending on personal interests.
However, guided tours are available upon request, with a one-week advance notice and additional cost, should you prefer a more detailed explanation of the sites’ history and architecture.
This 7-hour private tour offers a well-rounded day of sightseeing, culture, and culinary delights. The personalized service, delicious lunch, and wine tastings collectively create a memorable day in Tuscany.
While the self-guided exploration means fewer explanations at each site, the flexibility and private transport compensate well. It suits visitors who appreciate independent wandering combined with curated experiences, especially those interested in wine, food, and medieval towns.
This tour provides a convenient, intimate way to experience Volterra’s relics and San Gimignano’s towers, paired with a typical Tuscan lunch and wine tasting at a local farm. Its flexible, private setup makes it ideal for those who prefer their sightseeing unhurried and personalized.
The scenic drive, delicious food, and stunning towns make this a solid choice for visitors wanting a complete taste of Tuscany in a single day. Its high rating of 5.0 reflects strong satisfaction, particularly for those who value authentic regional cuisine and medieval architecture.
“The Tuscan countryside was beautiful. Daniel was a great driver. Lunch outside with the view of San Gimignano was priceless. Volterra is a hidde…”
Is this tour suitable for children?
While the tour is primarily designed for adults, children can enjoy the scenic drives, the open-air towns, and the lunch. However, self-guided exploration at sites may require supervision.
What is included in the wine tasting?
The wine tasting includes 5 different wines: Chianti, Chianti Riserva, Sangiovese, Vernaccia, and Brunello. You also sample extra virgin olive oils, balsamic vinegar, and truffle oil.
Can I request a guided tour instead of self-guided visits?
Yes, a pro guide can be booked one week in advance for an additional fee, providing more detailed explanations at each site.
How early should I book this tour?
The average booking window is 31 days in advance, but early reservations are recommended, especially during peak seasons.
Are entrance fees included?
No, both Volterra and San Gimignano are free to enter. The tour is based on self-guided exploration at each stop.
What should I wear for this tour?
Comfortable shoes for walking through towns and uneven streets are advisable. Dress according to the weather, especially if visiting during warmer months.
Is lunch included, and what does it feature?
Yes, a Tuscan lunch with bruschetta, pasta, cured meats, cheese, and dessert is included, along with wine tastings.
Can I customize this private tour?
Customization is possible with advance notice, including requesting a guide or adjusting the itinerary to suit your interests.