San Gimignano & Chianti wine tour: Private day with lunch

Medieval towers, cypress avenues, and wine tastings at two working farms in one day

A private full-day tour through the Chianti hills and San Gimignano, with hotel pickup and a driver who navigates the vineyard roads while you move between two family-run wineries for lunch and tastings. The day centers on a 3-course meal at the first farm (homemade pasta, Pecorino cheese, cold cuts) paired with Chianti, Vernaccia and Super Tuscan wines, then a second tasting of Chianti Classico at a traditional estate before return to your hotel. The route crosses olive groves, cypress avenues and the rolling Siena countryside, with free time in San Gimignano's medieval square.

Step-by-step itinerary

Explore Chianti hills with wine tastings

• Pickup from your location
• Drive through Tuscan hills
• Visit San Gimignano village
• Free time to explore and gelato tasting
• Lunch at family-run Tuscan winery
• Wine, olive oil, and balsamic tastings
• Drive along Siena countryside wine road
• Visit traditional Chianti winery
• Chianti Classico wine tasting
• Return to your location

The experience

Your driver collects you from your hotel or apartment and steers through the rolling Tuscan hills toward San Gimignano. The route passes between cypress trees, vineyards and olive groves, and you'll have free time in the walled medieval village itself, the "Town of Fine Towers", to walk the main square, browse artisan shops, or taste the gelato at Gelateria Dondoli. The village is also the source of Vernaccia di San Gimignano, the white wine you'll encounter later in the day.

Lunch happens at a family-run biodynamic farm with views back toward San Gimignano's towers. You'll sit in a garden or private tasting room and eat a 3-course menu: homemade pasta, bruschetta, Pecorino cheese, prosciutto, salame and cold cuts, followed by wine tastings of Chianti, Chianti Riserva, Sangiovese, Vernaccia and Super Tuscan. The farm also pours tastings of extra virgin olive oil, pepper olive oil, balsamic vinegar and truffle oil, so you're tasting the full range of what the estate produces rather than wine alone.

After lunch the driver takes you along one of the most beautiful Tuscan wine roads, crossing gentle hills surrounded by vineyards and cypress. The final stop is a traditional Chianti winery in the heart of the region, where you taste Chianti Classico and Chianti Classico Riserva: the wines marked with the Gallo Nero (Black Rooster) seal. Then it's a comfortable return to your hotel, ending the day around eight hours after pickup.

What’s included

• Private transportation and an air-conditioned vehicle with your driver.
• 3-course lunch with homemade pasta, Pecorino cheese, cold cuts and bruschetta.
• wine tastings at two family-run farms featuring Chianti, Chianti Riserva, Vernaccia, Sangiovese and Super Tuscan.
• tastings of extra virgin olive oil, pepper olive oil, balsamic vinegar and truffle oil.
• bottled water throughout the day.
• hotel or apartment pickup and return.

Before you book

Days and timesEvery dayDeparts at 09:00

AgesAdult (18 and older) · Youth (under 18)

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 8 days ago

Operated by Pek Tuscany in Limo

Is this one for you?The day runs eight hours with a driver handling all the roads, so you move between stops without navigating or driving yourself. The pace is leisurely, built around a long lunch and two seated tastings rather than rushed stops.

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Top questions

What languages is the guide in?

Live guide in English, Spanish, French and Italian.

Can children come?

Yes. Ticket types: Youth (under 18).

What is there to do in San Gimignano during the free time?

San Gimignano is a walled medieval village with a famous skyline of ancient towers, artisan shops, and local products including saffron and Vernaccia wine. The main square is the center, and Gelateria Dondoli is a well-known spot for gelato there.

How many wine tastings are included in this tour?

Two separate tastings at two different farms: the first at the lunch farm includes Chianti, Chianti Riserva, Sangiovese, Vernaccia and Super Tuscan. The second at the traditional Chianti winery features Chianti Classico and Chianti Classico Riserva. You also taste olive oils, balsamic and truffle oil at the lunch farm.

What does the 3-course lunch include?

The lunch at the family-run farm includes homemade pasta, bruschetta, Pecorino cheese, prosciutto, salame and cold cuts as the main courses, paired with the wine tastings. The meal is served in a garden or private tasting room overlooking the medieval towers.

How long is the full day, and what is the route like?

The tour runs about 8 hours from pickup to return. The route crosses rolling Tuscan hills through olive groves, cypress avenues and vineyards, with stops in San Gimignano, two wine farms, and the Chianti countryside between them.