Florence: Chianti Wineries & San Gimignano with Lunch & Tastings

Two Tuscan Wineries, One Afternoon, and Why You'll Want to Stay Longer

You visit two family-run Chianti wineries with cellar tours and tastings, stop in the medieval towers of San Gimignano with free time for gelato and exploring, eat an authentic Tuscan lunch with wine and olive oil tasting at the second farm, and finish at Piazzale Michelangelo for the classic Florence view. Small group (up to 8), air-conditioned transport, and a licensed guide who knows the route.

Step-by-step itinerary

Chianti wineries and medieval villages

• Visit first winery farm
• Guided wine, olive oil, food tastings
• Tour medieval Manhattan sites and towers
• Free time for shopping and gelato
• Authentic Tuscan lunch at second winery
• More wine tasting with local products
• Enjoy best view over Florence

The experience

There's something about standing in a wine cellar that makes you want to slow down. The air is cool, the light comes through stone, and someone who actually grows grapes is telling you why this one tastes different from the last. That's what pulls you into a Chianti wine tour from Florence, not the idea of wine, but the moment when you realize the person pouring it knows every vine. The day starts early, and you'll spend it in the rolling hills south of the city, visiting two working farms where the owners walk you through their cellars, explain the soil and the seasons, and let you taste what they make. It's small enough that you're not herded. Just eight people maximum in one minivan with a guide who knows which winery to hit first and which one saves the best lunch.

After the first tasting, you'll stop in San Gimignano, the medieval village with towers that rise like a skyline from the 1300s. The guide takes you through Piazza della Cisterna and Piazza del Duomo so you see the layout, then you're free to wander, grab gelato from Dondoli (the world champion gelato maker, which is a real thing), and poke into the narrow streets on your own time. It's not rushed, and it's not a photo stop. You get maybe an hour, which is enough to feel like you've been somewhere, not just passed through it. Then back to the second winery for lunch: homemade pasta, local cheeses, olive oil you can actually taste the difference in, and more wine. The tasting is guided, so you're learning as you eat, not just eating and drinking.

Before heading back to Florence, the route includes Piazzale Michelangelo, the overlook where the whole city spreads out below you: the Duomo, the Arno, the hills beyond. It's the view most people come to Florence for, and it lands at the end of the day when you're already thinking about what you've seen. The minivan is air-conditioned, the driver handles the roads (which wind), and everything (entry to the wineries, the lunch, the tastings, the transport) is already arranged. You don't negotiate with anyone, you don't figure out the bus schedule, you don't wonder if you picked the right place to eat.

What’s included

Your day includes pickup from Florence (or a central meeting point), transport in a comfortable air-conditioned minivan for up to 8 people, guided visits to two Chianti wineries with cellar tours, wine tastings at both farms, an authentic Tuscan lunch with homemade pasta, local cheeses, olive oil tasting, and more wine at the second winery, a stop in the medieval village of San Gimignano with free time to explore and buy gelato, a visit to Piazzale Michelangelo for the panoramic view of Florence, and a licensed tour guide and driver for the entire day.

Options for this experience

2 options

Chianti Wine Country Excursion with Medieval Villages, Lunch and Wine TastingsGuide in English, Spanish or Italian · 09:00Guided visit of San Gimignano with lunch and wine tastings, vineyard and wine cellar visits, in a comfortable 8-seat minivan with air conditioning

Chianti wine tour, privateGuide in English, Spanish or Italian · 09:00Customisable private experience: private round-trip transportation, private visits to the wineries, private wine tastings and lunch, and a private visit to San Gimignano

You pick the guide language when booking.

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

Before you book

Days and timesEvery dayDeparts at 09:00

Book up to10h before

AgesAdult (19 to 64 years) · Senior (65 and older) · Youth (16 to 18 years) · Child (3 to 15 years) · Infant (under 3)

GroupUp to 14

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.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 12 days ago

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by Fun In Tuscany

Is this one for you?Book this if you want to taste real Chianti wine from the people who make it, eat a proper Tuscan lunch, and see a medieval village: all without renting a car or figuring out the route yourself. Small groups mean you're not lost in a crowd, and the fixed itinerary is what lets a full day fit between breakfast in Florence and dinner back in the city.

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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: Youth (16 to 18 years); Child (3 to 15 years); Infant (under 3).

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

How long is the Chianti wine tour from Florence?

The tour runs for a full day. Exact duration depends on pickup location and return time, but plan for most of your daylight hours.

What's included in the price?

Entry to two wineries, guided cellar visits, wine tastings, Tuscan lunch with more tastings (wine, olive oil, cheeses, pasta), transport in a minivan, and a stop at Piazzale Michelangelo. The guide and driver are included.

How many people go on the tour?

Maximum 8 people per group, sharing one air-conditioned minivan.

Do I need to book in advance?

Yes, advance booking is required. This is a small-group tour, so spots fill up, especially in peak season.

Can I do this tour if I don't drink wine?

The tour centers on wine tastings, but you're not obligated to drink. You can taste and spit, or simply observe while others taste. Lunch and the village visit don't depend on wine.

What about dietary restrictions?

Inform the operator when you book if you have allergies or dietary needs. The lunch is traditional Tuscan, but they can often accommodate requests with advance notice.

Is there free time to explore on my own?

Yes. In San Gimignano, you get about an hour to walk around, shop, and eat gelato without the group. The winery visits are guided, but the pace is not rushed.

What if the weather is bad?

The tour runs in most weather. The minivan is enclosed and air-conditioned. Heavy rain or extreme conditions may affect the route, but the operator will confirm before the day.

Do I need to be fit or athletic?

No. The tour is suitable for all fitness levels. You walk through villages and wineries at a normal pace, but there are no hikes or strenuous activities.