Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

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Free cancellationTravelers' pick

1/26

Duration7h

GroupUp to 16

LanguagesEN

Mobile ticketAccepted

Two Tuscan Wineries & San Gimignano's Medieval Towers in One Day from Florence

You meet your guide at Piazza della Calza at 9:45am and spend seven hours visiting two family-run wineries in the Chianti region, tasting eight wines plus olive oils and balsamic vinegar with local snacks. You'll walk through San Gimignano's medieval streets and towers, then return to Florence by 5:00pm. The minivan holds eight people, so groups stay manageable, and an English-speaking guide handles all the driving and commentary.

Step-by-step itinerary

Tuscany wineries and San Gimignano visit

Meet at Piazza della Calza at 9:45am
Drive to first winery in Ulignano
Taste wines and local delicacies at first winery
Visit second winery near San Gimignano
Taste wines including Vernaccia and rosé
Explore San Gimignano medieval town
Return to Florence by 5:00pm

The Experience

Your guide meets you at the "P" parking sign in Piazza della Calza by Porta Romana at 9:45am, wearing a purple T-shirt so you can't miss them. They'll run through the day while you settle into the air-conditioned minivan — eight seats, which means the group stays small enough that you're not herded through the wineries like a school trip. The drive to the first winery takes about an hour, and your guide fills it with stories about Tuscany's history and the landscape rolling past the windows: vineyards, olive groves, cypress trees standing like punctuation marks on the hillsides. By the time you arrive at the family-run estate near Ulignano, you've already started to understand why people come back to this region.

The first winery sits in the Chianti heartland, and you'll taste Chianti, Super Tuscans, and Vernaccia di San Gimignano paired with bruschetta, local cheeses, and other Tuscan snacks. It's not a rushed tasting — the estate has a welcoming atmosphere and the guide knows the producers, so there's actual conversation instead of just pouring. Then it's a short drive, maybe five kilometers, to the second winery closer to San Gimignano. Here you taste three more wines: Vernaccia again (but different producers taste different), Chianti Colli Senesi, and a rosé. By now you've sampled eight different wines, three extra virgin olive oils, and balsamic vinegar. You've also probably met other travelers in the group and started making plans to grab dinner together later.

San Gimignano itself is the kind of place that stops you. The town is called the "Medieval Manhattan" because of its skyline of ancient towers — some of them fourteen stories high, built by rival families centuries ago as symbols of power and wealth. You walk through narrow cobblestone streets, past the Piazza del Duomo and the Collegiata cathedral, and into artisan shops selling saffron, local wines, and ceramics. There's time to wander, to sit on a bench and look at the view, to buy something small you didn't plan on. The guide doesn't rush you; they know this is the part people remember.

The drive back to Florence takes about an hour. You're dropped at the starting point in Piazza della Calza by 5:00pm, which gives you the evening to rest or explore the city. The tour requires a minimum of four participants; if the group doesn't reach that, a private option is available for an additional fee. You need to be at least 18 years old, and if you have dietary requirements, mention them when you book.

What’s included

Your day includes hotel pickup via minivan (8 seats, air-conditioned), a one-hour scenic drive through Chianti with guide commentary, a guided tasting at the first winery with Chianti and Vernaccia paired with bruschetta and local cheeses, a second winery visit with three more wines and balsamic vinegar, free time to explore San Gimignano's medieval streets and towers, and return transport to Piazza della Calza by 5:00pm. An English-speaking guide accompanies the entire experience.

Good to know

Easy physical levelPublic transport nearby

Operated by Italy on a Budget tours

Is this one for you?Book this if you want to taste real Tuscan wines at family-run estates and see San Gimignano's medieval towers without arranging your own transport, timing, or winery bookings — the fixed schedule and small group size mean you get a full day of Tuscany without the logistics.