Volterra & San Gimignano private wine tasting tour from Siena

Walk Volterra's Roman Theater and medieval towers, taste five wines at a working farm

A private full-day tour from Siena visits Volterra's Roman Theater and historic streets, then moves to a family-run Tuscan farm for lunch with five wine tastings, before ending in San Gimignano's walled medieval town. Your driver handles the route through Chianti hills. You explore each stop at your own pace and return by 5pm.

Step-by-step itinerary

Explore Volterra and San Gimignano

• Meet your driver at location
• Drive through Tuscan countryside to Volterra
• Self-guided tour of Volterra's historic sites
• Travel to Tuscan farm for lunch and wine tasting
• Enjoy Tuscan lunch with 5 wine tastings
• Drive through Chianti hills to San Gimignano
• Self-guided tour of San Gimignano and towers
• Taste gelato at Gelateria Dondoli
• Return to your location

The experience

The day starts with pickup from your hotel or flat in Siena, then a drive through rolling Tuscan countryside (olive groves, vineyards, cypress rows) to Volterra. Once there, you walk the historic city on your own, moving between the 4th-century Etruscan Arch, the octagonal Baptistery, the Duomo, and the Palazzo dei Priori. The Roman Theater sits at the edge of town and offers one of the best viewpoints in Tuscany. Volterra is also known for alabaster workshops, so there's time to browse if that interests you.

Lunch happens at a family-run organic farm in the Chianti zone. You eat bruschetta, lasagna or homemade pasta, cured meats, pecorino cheese and dessert, paired with tastings of five wines: Chianti Rosso, Chianti Riserva, Sangiovese, Vernaccia, and a Rosé. The farm also offers tastings of extra virgin olive oil, balsamic vinegar, pepper oil and truffle oil, so you leave understanding how Tuscan producers work and what makes their combinations work. After lunch, the drive to San Gimignano cuts through the Chianti wine road and the Siena hills.

San Gimignano's walled medieval town is your final stop, explored on your own for about an hour. The "Town of Fine Towers" once held over 70 towers. Now roughly a dozen remain, making it feel like an open-air museum. The town is known for saffron, the Golden Ham, and Vernaccia di San Gimignano wine. In the main square, Gelateria Dondoli serves ice cream worth the detour. The return to Siena is expected around 5pm.

What’s included

• Your private driver handles all transportation from Siena and back.
• the air-conditioned vehicle comes with bottled water. Lunch at the farm includes five wine tastings plus tastings of olive oil, balsamic vinegar, pepper oil and truffle oil. Your driver speaks English, Spanish, Italian or French, depending on availability.

Before you book

Days and timesEvery dayDeparts at 08:30

Book up to2d before

AgesAdult (18 and older) · Youth (1 to 17 years)

GroupPrivate

Live guideEnglish, Spanish, French and Italian

Meeting point and pickupHotel pickup included.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 10 days ago

Good to know

Low physical effortWheelchair accessibleStroller-friendlyInfant seats available

Operated by Pek Tuscany in Limo

Is this one for you?Choose this private tour if you're exploring Volterra and San Gimignano solo or with companions. Your driver waits at each stop while you set your own pace, and lunch with wine tastings at a working farm is included rather than booked separately.

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Top questions

What languages is the tour guided in?

Live guide in English, Spanish, French and Italian.

Can children come?

Yes. Ticket types: Youth (1 to 17 years).

What is the Roman Theater in Volterra like when you get there?

Volterra's Roman Theater sits at the edge of the historic city and is one of the best viewpoints in Tuscany. It dates back to the Roman period and remains one of the town's most significant attractions, visible from many angles as you walk through the streets.

How does the wine tasting work at the farm?

The farm tasting includes five wines (Chianti Rosso, Chianti Riserva, Sangiovese, Vernaccia, and Rosé) served during lunch alongside bruschetta, pasta, cured meats and cheese. You also taste extra virgin olive oil, balsamic vinegar, pepper oil and truffle oil, so you learn how each one pairs with food and how Tuscan producers make them.

Can you spend as much time as you want in San Gimignano, or is it rushed?

San Gimignano is a self-guided stop with about an hour to explore. That is enough time to walk the walled medieval town, see the towers, and visit the main square where Gelateria Dondoli sits. If you want longer, you can arrange that with your driver.

What happens if you have dietary restrictions or allergies?

The farm lunch includes bruschetta, lasagna or homemade pasta, cured meats, pecorino cheese and dessert. Let your driver know about any restrictions when you book, so the farm can prepare alternatives or adjustments for you.

Is there time to shop for souvenirs in Volterra?

Volterra is famous for alabaster craftsmanship and salt quarries, and the self-guided portion of the visit gives you time to browse workshops and shops if you want to buy something. The town's artisan work is distinctive to the region.