Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

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.

Options for this experience

2 options

Coach standard group tourGuide in English · Available from 27 Mar 2027Enjoy a shared group outing with up to 49 travelers, riding in a comfortable and spacious coach that suits larger groups.

Minivan small group tourGuide in English · 10:00Experience an intimate small group outing with a maximum of 8 travelers, riding in a comfortable minivan.

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

Before you book

Days and timesMonday to SaturdayDeparts at 10:00

Book up toStart time

AgesAdult (18 and older) · Under 18: can't be booked

GroupUp to 16

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

Prices and times updated today

Good to know

Low physical effortPublic 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.

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Top questions

What time does the tour start and where do I meet the guide?

Meet at the "P" parking sign in Piazza della Calza by Porta Romana at 9:45am. The tour departs at 10:00am.

How many wines do I taste on this tour?

You taste up to 8 different types of wine across the two wineries, plus three extra virgin olive oils and balsamic vinegar with Tuscan snacks.

Is San Gimignano included in the tour?

Yes. You visit San Gimignano in the afternoon and have time to walk through the medieval town, see the towers, and explore the streets before returning to Florence.

What is the total duration of the tour?

The tour runs approximately 7 hours, from 10:00am to 5:00pm, including travel time, two winery visits, and time in San Gimignano.

Is transport from my hotel included?

No. You meet the guide at Piazza della Calza. Public transportation options are available nearby if you need to reach the meeting point.

What is the minimum group size?

The tour requires a minimum of 4 participants. If the group doesn't reach four, a private option is available for an additional supplement.

Can I join if I have dietary restrictions?

Yes. Advise any specific dietary requirements at the time of booking, and the guide will accommodate them.

Is there a minimum age requirement?

Yes, you must be at least 18 years old to participate.

What is included in the tour price?

Includes transport in an air-conditioned minivan, guided visits to 2 wineries, wine and olive oil tastings, Tuscan snacks, and time in San Gimignano. An English-speaking driver/guide leads the experience.