Chianti & Montalcino Wine Tour from San Gimignano

Two wineries in one day means tasting Chianti and Brunello side by side, with lunch and vineyard views between them.

A full-day wine tour from San Gimignano takes you through the Tuscan countryside to two working wineries: one in Chianti, the other in Montalcino, world-famous for Brunello. You taste at both, eat a traditional lunch with regional products, and get free time to walk Montalcino's medieval streets before returning to San Gimignano. The tour runs eight hours and includes air-conditioned transport, a professional guide in English, Spanish or Italian, and all tastings and meals.

Step-by-step itinerary

Wine tasting and sightseeing tour

• Meet guide at Porta San Giovanni
• Travel to Tuscan countryside winery
• Wine tasting with regional products
• Enjoy traditional Tuscan lunch
• Travel to Montalcino wine area
• Wine tasting with regional specialties
• Free time exploring Montalcino center
• Return to San Gimignano

The experience

The day starts at Porta San Giovanni in San Gimignano, where you meet your guide and board an air-conditioned minivan. From there, the route heads into rolling vineyard country to the first winery in the Chianti region. You taste wines there, paired with typical regional products (cheeses, cured meats, bread), and sit down to a traditional Tuscan lunch. The winery visit and tasting take about an hour and a half.

After lunch, the minivan carries you south toward Montalcino, the hilltop town known for Brunello di Montalcino, one of Italy's most prestigious red wines. At the second winery, you taste again, this time with regional specialties, and spend about thirty minutes there. The vineyard views from Montalcino are the landscape the tour is built around: rolling hills that stretch to the horizon, and the vines themselves at different seasons.

Once the tasting ends, you have an hour and a half of free time to explore Montalcino on your own. The medieval center is small enough to walk in that window: narrow streets, stone buildings, a fortress at the top, and views back over the countryside you just drove through. Then the minivan returns you to San Gimignano, arriving in the late afternoon.

What’s included

• Air-conditioned minivan transport from San Gimignano to both wineries and back.
• a professional tour guide.
• tastings at two wineries with regional specialties paired at each.
• a traditional Tuscan lunch at the first winery.

Before you book

Days and timesMonday, Thursday and SundayDeparts at 11:30

Book up to12h before

AgesAdult (13 and older) · Child (3 to 12 years) · Infant (under 3): free

GroupUp to 29

Live guideEnglish, Spanish and Italian

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

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

Prices and times updated today

Good to know

Low physical effortPublic transport nearbyNot recommended during pregnancyNot recommended with back problems

Operated by myTour in Italy

Is this one for you?Book this if you want to visit two separate wine regions in one day with a guide handling all the driving and route planning between San Gimignano and Montalcino.

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Top questions

What languages is the tour guided in?

Live guide in English, Spanish and Italian.

Can children come?

Yes. Ticket types: Child (3 to 12 years); Infant (under 3): free.

What's the difference between the two wineries on this tour?

The first winery is in Chianti, the region known for its lighter, more elegant reds. The second is in Montalcino, where Brunello di Montalcino (a fuller, more structured wine) is made. Tasting both in one day lets you compare the two regions' styles side by side.

How much free time do I get in Montalcino?

You have an hour and a half to explore the medieval center on your own after the winery tasting. That's enough time to walk the main streets, climb to the fortress if you want the views, and stop for a coffee or gelato.

Is lunch included, and what kind of food is it?

Lunch is included at the first winery and consists of traditional Tuscan dishes paired with regional products like local cheeses and cured meats. It's served as part of the winery visit, not as a separate stop.