Florence: Chianti Wine Tasting & San Gimignano with Lunch

Two Wineries, One Medieval Village, and Lunch in Tuscany Wine Country

You get hotel pickup, a panoramic stop at Piazzale Michelangelo, an hour in San Gimignano's medieval streets, lunch with wine at a Tuscan farmhouse, and tastings at two separate wineries: all in one afternoon without arranging transport, timing stops, or choosing which wines to try. The fixed itinerary and small-group format mean you're not negotiating logistics. You're just moving through the day.

Step-by-step itinerary

Tuscan wine tour and San Gimignano visit

• Pick up at 8:00 AM
• Drive 15 minutes to Piazzale Michelangelo
• Enjoy panoramic view of Florence
• Drive 1 hour to San Gimignano
• Visit San Gimignano for 1 hour 25 minutes
• Drive 50 minutes to Tuscan farmhouse
• Lunch and wine tasting for 2 hours 30 minutes
• Drive 25 minutes to San Michele a Torri winery
• Wine tasting for 45 minutes
• Drive 40 minutes back to pick up point

The experience

You're picked up at 8am from your Florence hotel, or from the meeting point near Santa Maria Novella station if you're staying outside the historic center. The van is a black Mercedes, air-conditioned, with WiFi already running and a bottle of water waiting for you. Fifteen minutes later you're at Piazzale Michelangelo, where the city spreads out below you in one long view: the Duomo, the Arno, the terracotta roofs. You stand there for a moment, and then it's time to drive toward Chianti.

An hour north takes you to San Gimignano, the walled medieval town famous for its towers: fourteen of them still standing, built by rival families centuries ago in a kind of vertical arms race. You have an hour and twenty-five minutes to walk the narrow streets, eat the ice cream everyone mentions, and let the place settle into your memory. It's the kind of village that looks exactly like the postcard, which is either perfect or slightly unreal depending on your mood. After that, you drive fifty minutes deeper into wine country toward a family farmhouse in the Chianti region. Lunch happens here: regional food, multiple Chianti wines, olive oil tasting, and two and a half hours to sit in the Tuscan countryside without rushing. The view from the table doesn't hurt either.

At 2:30pm you drive twenty-five minutes to San Michele a Torri, a smaller family-run estate where you taste more Chianti. Five or six different types by the time you're done, which is what the tour operator says you need to actually know the region. Forty-five minutes there, then a forty-minute drive back to Florence. You arrive around 4:30pm, which leaves your evening open. The whole day is eight hours, max eight people per van, and the Prosecco happy hour happens somewhere in the middle, though the timing depends on the group's pace.

What’s included

Your day includes hotel pickup at 8am (or meeting point near Santa Maria Novella station), a stop at Piazzale Michelangelo for Florence views, one hour and twenty-five minutes in San Gimignano village, a two-and-a-half-hour Tuscan lunch with wine at a Chianti farmhouse, wine and olive oil tastings at two separate estates, one bottle of Prosecco per group, bottled water, air-conditioned Mercedes van with WiFi and pocket hotspot for each couple, and hotel drop-off around 4:30pm.

Options for this experience

2 options

Morning tour in a semi-private groupGuide in English · 08:00Pickup is included

Special daysGuide in English · 08:00Pickup is included

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 08:00

Book up to12h before

GroupUp to 8

Live guideEnglish

Meeting point and pickupHotel pickup is optional; you can also go straight to the meeting point. Ends back at the starting point.You can choose from 4 pickup points.

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 8 days ago

Good to know

Low physical effortWheelchair accessibleStroller-friendlyInfant seats availablePublic transport nearby

Operated by I Just Drive

Is this one for you?Book this if you want the main Chianti wine experience and San Gimignano in one afternoon without arranging your own transport, choosing which wineries to visit, or timing the day yourself: the fixed schedule and small-group van mean you show up and move through it all.

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Top questions

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.

What time does the tour start and where do I get picked up?

Pickup is at 8am. Hotels in Florence's historic center (Zone A) offer direct pickup. All other locations meet at Tino Caffè, Via della Scala 59, one minute from Santa Maria Novella station. Arrive 15 minutes early.

How long is the tour and when do I get back?

The full tour is eight hours. You depart at 8am and return around 4:30pm, leaving your evening free.

Is lunch included?

Yes. Lunch is a Tuscan meal at a farmhouse in the Chianti region, paired with local wines. The meal lasts about two and a half hours.

How many wineries do I visit?

Two. The first is a farmhouse cellar in the Chianti area where you have lunch. The second is a family-run estate at San Michele a Torri where you taste additional Chianti wines.

What's included in the price?

Hotel pickup and drop-off, Piazzale Michelangelo stop, San Gimignano village time, Tuscan lunch, wine and olive oil tastings at both wineries, one bottle of Prosecco per group, bottled water, air-conditioned van, and WiFi on board.

How many people travel together?

Maximum eight people per Mercedes van. The tour is described as semi-private, meaning you may share the van with other small groups.

Do I need to be fit or mobile for this tour?

The tour is suitable for all fitness levels. It's wheelchair accessible, and San Gimignano involves walking through a medieval village on uneven streets, but there's no strenuous hiking.

Can I bring children or infants?

Yes. Infants can travel in a pram or stroller, and specialized infant seats are available. The pace is leisurely enough for families.

What if I don't drink wine?

The tour centers on wine tasting, but you can participate at your own pace. Lunch and the village visit are the main non-wine elements of the day.

Is there a discount for breakfast before the tour?

Yes. As a Just Drive guest at Tino Caffè (the meeting point), you receive a 10% discount on breakfast: English, continental, or just a cappuccino.