Siena & San Gimignano tour from Florence: Chianti winery dinner

Siena's Piazza del Campo, San Gimignano's stone towers, and a Tuscan dinner in the Chianti countryside

This afternoon tour from Florence takes you through Chianti to Siena for a guided walking tour of its Contrade and Gothic landmarks, then to San Gimignano for free time in the medieval town, and ends with a typical Tuscan dinner and wine tasting at a winery in the countryside. The tour runs 9 to 12 hours and includes transportation in a luxury minivan, an English-speaking guide, and a surprise tasting in Siena. The Tuscany Grand Tour option adds Pisa and a traditional lunch if you want a full-day experience starting at 8 AM.

Step-by-step itinerary

Tuscany towns and winery dinner

• Meet at Florence meeting point
• Guided tour of Siena
• Free time in San Gimignano
• Dinner and wine tasting at Chianti winery
• Return to Florence meeting point

The experience

The day starts at your Florence meeting point and moves into the Chianti hills in a luxury minivan. You arrive in Siena for a guided walking tour that covers the Contrade neighborhoods and Piazza del Campo, the shell-shaped square ringed by medieval palaces where the Palio horse race runs twice a year. A surprise tasting of local specialties happens before you leave the city.

San Gimignano comes next: a UNESCO-listed town famous for its surviving tower houses that rise from the medieval streets. You have free time to walk the town at your own pace, climb the towers if you want, and eat lunch on your own (not included). The winery sits in the Chianti countryside, and as the sun sets you sit down to a typical Tuscan dinner paired with wine tasting. The return to Florence and your starting point closes the tour.

If you want more, the Tuscany Grand Tour option starts at 8 AM and adds a stop in Pisa to see the Piazza dei Miracoli and the Leaning Tower (tower entry is not included and costs extra if you buy it on-site), plus a traditional Tuscan lunch instead of the dinner. That version runs the full day. The tour runs in any weather, and infants can travel in a pram or specialized seat. Free WiFi is on board throughout.

What’s included

• Luxury minivan transportation from Florence.
• English-speaking driver and tour guide.
• guided walking tour of Siena with its Contrade and Piazza del Campo.
• surprise tasting of local specialties in Siena.
• free time in San Gimignano.
• typical Tuscan dinner and wine tasting at a boutique winery in Chianti.
• free WiFi on board.

Options for this experience

4 options

Essential Coach Tour and DinnerGuide in English · 13:00 and 14:00Afternoon tour with dinner covering Siena and San Gimignano by coach, featuring top Tuscan sights and a typical dinner at a winery, a great experience at a budget-friendly price

Small Group: Siena and DinnerGuide in English · 13:00 and 14:00Afternoon tour of Siena and San Gimignano with dinner, in a premium small group of up to 20 people by Mercedes minivan, a top-tier tour that includes a winery dinner

Tuscany Grand Tour, semi-privateGuide in English · 08:00Upgrade to the Grand Tour: a full-day, 12-hour tour departing at 8 AM covering Siena, San Gimignano, Chianti, Pisa and a Tuscan lunch, a semiprivate journey limited to 8 people, done in style

Private tour of Siena and San Gimignano with dinnerGuide in English · 08:00, 13:00 and 14:00Private Group: Siena and Dinner, a private afternoon in Siena and San Gimignano with a traditional winery dinner

You see the exact price of each option when you check availability.See dates & prices

Before you book

Days and timesEvery dayDepartures at 08:00, 13:00 and 14:00

Book up toStart time

AgesAdult (13 and older) · Child (4 to 12 years) · Infant (under 4)

GroupUp to 20

Live guideEnglish

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

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by Towns of Italy

Is this one for you?Choose the standard afternoon tour if you want the highlights of Siena, San Gimignano and Chianti wine without committing to a full day. Pick the Tuscany Grand Tour option if you're staying longer and want to add Pisa, a traditional lunch, and an earlier start so you see more of Tuscany in one journey.

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Top questions

Can children come?

Yes. Ticket types: Child (4 to 12 years); Infant (under 4).

What is the Piazza del Campo in Siena, and what will I see there on the walking tour?

Piazza del Campo is the main square of Siena, famous for its shell shape and the twice-yearly Palio horse race. On the guided walking tour you'll see the medieval palaces that ring it and learn about the Contrade neighborhoods that compete in the race.

How much free time do I get in San Gimignano, and what can I do there?

San Gimignano is a UNESCO heritage site known for its medieval towers. You have free time to wander the streets, climb the towers if you choose, and eat lunch at a restaurant of your choice (lunch is not included in the tour price).

What wine and food will I taste at the winery?

The tour includes a typical Tuscan dinner and wine tasting at a boutique winery in the Chianti countryside. Siena also includes a surprise tasting of local specialties earlier in the day.

Is hotel pickup included, or do I meet the tour in Florence?

You meet the tour at a designated meeting point in Florence. Hotel pickup and drop-off are not included, though public transportation options are available nearby.

What's the difference between this tour and the Tuscany Grand Tour option?

The standard tour is an afternoon experience ending with dinner at the winery. The Tuscany Grand Tour option starts at 8 AM, adds a full-day itinerary that includes Pisa and the Leaning Tower, and replaces the dinner with a traditional Tuscan lunch. It runs longer and covers more ground.

Is the tour affected by bad weather?

The tour operates regardless of weather conditions, so rain or cold will not cancel it or change the itinerary.