San Gimignano & Chianti Hills Tour: Lunch & Wine Tasting

You taste wine at two different farms, not just one tasting room.

A private full-day tour through the Chianti hills and San Gimignano with a personal driver, hotel pickup, and a three-course lunch at a family-run organic farm paired with wine tastings at two separate wineries. The route crosses olive groves and cypress-lined roads to the medieval towers of San Gimignano, then stops at Monteriggioni Castle before ending with Chianti Classico tasting on the way back.

Step-by-step itinerary

Chianti Hills and San Gimignano Tour

• Meet driver at your location
• Drive to San Gimignano
• Explore San Gimignano medieval town
• Drive through Chianti hills
• Lunch at family-run Tuscan farm
• Wine and oil tasting at farm
• Visit Monteriggioni Castle and museum
• Wine tasting at Chianti Classico winery
• Return to your hotel or apartment

The experience

Your driver picks you up at your hotel and drives you through rolling Chianti landscape (olive groves, cypress avenues, vineyards) to San Gimignano, where you explore the medieval town on your own. The towers are the draw here, along with the shops and the main square. The itinerary mentions Gelateria Dondoli if you want gelato. From there you head to a family-run organic farm for lunch: bruschetta, homemade pasta or lasagna, Tuscan ham, pecorino cheese, and dessert, paired with five wines including Chianti, Chianti Riserva, Sangiovese, and Vernaccia. The farm overlooks San Gimignano's towers across the hills.

After lunch you visit Monteriggioni Castle, built by Siena between 1213 and 1219 as a fortress against Florence. Inside is a museum of medieval weapons. On the return journey you stop at a second winery (one of several Chianti Classico producers in the area) for a tasting of Gallo Nero and other wines. The full day ends by 5 p.m. at your hotel.

The tour runs with a personal driver who speaks English, Spanish, Italian or French. The vehicle is air-conditioned and includes bottled water. Children from age one are welcome, and infant seats are available.

What’s included

• Private transportation in an air-conditioned vehicle.
• hotel or apartment pickup and return.
• personal driver speaking your choice of English, Spanish, Italian or French.
• self-guided exploration of San Gimignano.
• three-course lunch at a family organic farm with bruschetta, homemade pasta, Tuscan ham, pecorino cheese and dessert.
• five wine tastings during lunch.
• visit to Monteriggioni Castle with medieval weapons museum.
• second wine tasting at a Chianti Classico winery.
• bottled water throughout the day.

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 7 days ago

Good to know

Easy physical levelWheelchair accessibleStroller friendlyInfant seats availablePublic transport nearby

Operated by Pek Tuscany in Limo

Is this one for you?Eight hours leaves room for a full day in the region without an overnight stay, but rules out combining this with other major attractions in the city you're staying in. Plan it as your day in the countryside.

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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 (1 to 17 years).

What is San Gimignano known for besides the towers?

San Gimignano is celebrated for its saffron, Prosciutto d'Oro cured meat, and Vernaccia di San Gimignano wine made from ancient local grapes. The town is also famous for its gelato, particularly at Gelateria Dondoli, a two-time world champion.

How many wines do I taste during the day?

You taste wines at two separate stops: five wines during lunch at the farm (Chianti, Chianti Riserva, Sangiovese, Vernaccia), and then Gallo Nero and other Chianti Classico wines at a winery on the return drive.

What does lunch at the farm include?

Lunch is three courses with bruschetta, homemade pasta or lasagna, Tuscan ham, Tuscan cold cuts, pecorino cheese from Pienza, and dessert, paired with the five wine tastings. The farm also offers tastings of extra virgin olive oil, pepper olive oil, balsamic vinegar, and truffle oil.

What is Monteriggioni Castle and why stop there?

Monteriggioni is a medieval fortress founded by Siena between 1213 and 1219 as an outpost against Florence. It was known as an impregnable fortress in antiquity, and today you can visit a museum of medieval weapons inside the castle walls.

What time does the tour end?

The return to your hotel is expected by 5 p.m., making the full day eight hours from pickup.