Small Group Wine Tour Florence: Two Wineries & San Gimignano

Taste Chianti at two working wineries, then wander a medieval hilltop town and end overlooking Florence

This eight-hour small group tour from Florence visits two Chianti wineries with guided tastings and a cellar tour, includes a traditional Tuscan lunch at the second winery, stops in the medieval village of San Gimignano for gelato and free time to explore, and ends at Piazzale Michelangelo for views across the city. An air-conditioned minivan carries the group. A live guide in English, Spanish or Italian narrates the route. Hotel pickup and drop-off are available for an additional charge.

Step-by-step itinerary

Wine tour and San Gimignano visit

• Visit first winery in Chianti
• Tour medieval San Gimignano
• Try world champion Dondoli gelato
• Visit second winery for lunch and tasting
• Stop at Piazzale Michelangelo viewpoint

The experience

The day starts in the Chianti region at an organic farm where you tour the vineyards and cellar to see how Chianti wines are made and aged, and learn the process behind Tuscan extra virgin olive oil. A guided wine tasting follows, and you have the chance to buy bottles at lower prices than you'll find in shops. The winery sits in the heart of the region, so the landscape itself is part of the stop: rolling hills, stone buildings, the working production you're standing inside.

From there the minivan climbs to San Gimignano, a medieval town perched on a hilltop with narrow streets and views across the Tuscan countryside. You get a guided walk through the main squares, then free time to wander, shop and eat gelato made by Dondoli, a world championship winner. The town is small enough to cover on foot but dense enough that an hour or two disappears into the alleys and the light.

The second winery is where lunch happens: a traditional Tuscan light meal paired with a wine tasting of the winery's own production. Vegetarian options are available if you request them when booking. After lunch, the route back to Florence includes a stop at Piazzale Michelangelo, a plaza overlooking the city with a replica of Michelangelo's David in the center and views that rank among Europe's most photographed. The minivan is air-conditioned throughout, and the guide provides live commentary on the drive.

What’s included

• Transport by air-conditioned minivan.
• guided tour of two Chianti wineries with cellar and vineyard access.
• two wine tastings.
• traditional Tuscan light lunch at the second winery.
• guided walk through San Gimignano with free time to explore and shop.
• gelato from a world champion maker.
• stop at Piazzale Michelangelo.
• live guide commentary throughout the day.

Information

Lasts 8h, runs every day at 09:00, from € 190 per person, with a live guide in English, Spanish and Italian and with free cancellation up to 24 h before.

Days and timesEvery dayDeparts at 09:00Other times ›

Book up to10h before

AgesAdult (18 to 65 years) · Senior (66 and older) · Youth (13 to 17 years) · Child (3 to 12 years) · Infant (under 3)

GroupUp to 16

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 2 days ago

Good to know

Low physical effortStroller-friendlyInfant seats available

Operated by Chianti Wine Tour

Is this one for you?Small groups keep the pace relaxed and the minivan intimate. You're not on a coach with forty people, so the winery staff can spend time with you and the stops in San Gimignano and at Piazzale Michelangelo don't feel rushed. The eight-hour loop fits a single day from Florence without requiring a separate car rental or navigation.

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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 (13 to 17 years); Child (3 to 12 years); Infant (under 3).

What exactly happens at the first winery in Chianti?

The first winery is an organic farm where you tour the vineyards and the cellar to see Chianti wine production and ageing firsthand, learn how extra virgin olive oil is made, and taste wines from the winery. You can buy bottles at lower prices than retail.

Is lunch included in this tour?

Yes, a traditional Tuscan light lunch is included at the second winery and is paired with a wine tasting of that winery's wines. Vegetarian options are available if you request them at the time of booking.

How much free time do you get in San Gimignano?

The tour includes free time in San Gimignano to explore the narrow streets, shop and try gelato from Dondoli, the world championship gelato maker. The guided walk through the main squares happens first, then you're free to wander on your own.

What is Piazzale Michelangelo and why is it on the route?

Piazzale Michelangelo is a plaza overlooking Florence with a replica of Michelangelo's David and views across the city. It's one of the most romantic viewpoints in Europe and is the final stop on the way back to Florence.

Can the tour pick me up from my hotel?

Hotel pickup and drop-off are available upon request for an additional charge. You can arrange this when you book the tour.