Tuscany Wine Tour from San Gimignano: 2 Wineries & Chianti

Taste your way through Chianti without worrying about who drives home.

This Tuscany wine tour from San Gimignano visits two working wineries in the Chianti region where you taste up to 9 wines (Chianti Classico, Vernaccia, rosé, and Super Tuscan) plus truffle oil, balsamic vinegar and snacks, guided in English with roundtrip transport included. You choose your departure point: the Tuscany on Wheels office outside San Gimignano or the town center itself, and the tour wraps by early afternoon or late afternoon depending on where you start. Minimum age is 18.

Step-by-step itinerary

Tuscan wineries and San Gimignano visit

• Start from chosen departure point
• Visit first winery and taste 5 wines
• Sample balsamic vinegar and olive oil
• Visit second winery near San Gimignano
• Taste 3 wines and tour vineyards
• Stroll in San Gimignano and see towers
• Return to Tuscany on Wheels office or end in San Gimignano

The experience

You start from either Tuscany on Wheels headquarters a few kilometers outside San Gimignano (with free parking) or directly from San Gimignano town center, depending on which option you booked. The guide meets you there and handles all the driving for the next six hours, which means you can taste freely without calculating who stays sober. The first winery sits an hour outside Florence in the heart of the Chianti region. A working vineyard where the producer walks you through five wines: Chianti Classico, Vernaccia, and a Super Tuscan among them. You also taste a 30-year-old balsamic vinegar and truffle-infused extra virgin olive oil, learning to recognize the flavors that separate one from another.

The second stop is a local winery overlooking San Gimignano's towers, known for D.O.C.G. Vernaccia white wine. The winemakers guide you through the vineyards and cellars, explaining how they make wine and oil, and which pairings work on the plate. You taste three more wines here (Vernaccia white, rosé, and Chianti Colli Senesi), and have the chance to buy bottles or local products to take home or ship. By the time you leave, you've tasted up to nine wines in a single afternoon without arranging a driver or navigating between stops yourself.

Before heading back, the tour includes free time in San Gimignano to walk the medieval streets and climb the 14 towers that define the skyline: built centuries ago as symbols of family power and still the town's main draw. If you started from San Gimignano, your tour ends there around 2:30 pm and you skip the return drive. If you started from the Tuscany on Wheels office, you return there around 4:30 pm. Either way, the transport, guide, tastings and snacks are all arranged. You just show up and taste.

What’s included

• An English-speaking guide for the full tour.
• roundtrip transportation from your choice of starting point.
• tastings of up to 9 Tuscan wines across two working wineries.
• samples of truffle-infused extra virgin olive oil and 30-year-old balsamic vinegar.
• snacks.
• and free time to explore San Gimignano's medieval towers and streets.

Options for this experience

2 options

From San GimignanoGuide in English · 11:30Small group tour departing from San Gimignano. Meeting point: Bivio Volterra, 53037 San Gimignano, Province of Siena, Italy

Departing from Tuscany on WheelsGuide in English · 10:30Small group tour departing from the Tuscany on Wheels office in Chianti. Meeting point: Tuscany on Wheels - Tours in & from San Gimignano, Strada di Sant' Appiano, 9/i, 50028 Barberino Tavarnelle FI, Italy

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

Before you book

Days and timesEvery dayDepartures at 10:30 and 11:30

Book up toStart time

AgesAdult (18 and older) · Under 18: can't be included in the booking

GroupUp to 16 · max 8 per booking

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

Easy physical levelPublic transport nearby

Operated by Italy on a Budget tours

Is this one for you?Choose the San Gimignano departure if you're staying in town and want to skip the drive back to the office. Pick the Tuscany on Wheels start if you're based outside town and want the full afternoon loop with a later return.

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Top questions

Can I start the tour from San Gimignano instead of the Tuscany on Wheels office?

Yes. You choose your departure point when you book: either from Tuscany on Wheels headquarters outside San Gimignano with free parking, or directly from San Gimignano town center. If you start from San Gimignano, the tour ends there around 2:30 pm instead of returning to the office at 4:30 pm.

What wines do I taste on this Chianti tour?

You taste up to 9 Tuscan wines across the two wineries: at the first winery, Chianti Classico, Vernaccia, and a Super Tuscan, plus a 30-year-old balsamic vinegar and truffle oil. At the second winery near San Gimignano, Vernaccia white, rosé, and Chianti Colli Senesi D.O.C.G.

Is lunch included, or do I need to eat before the tour?

Lunch is not a separate meal on this tour. You receive snacks and tastings of truffle oil and balsamic vinegar at the wineries, but you should plan to eat before or after the tour if you want a full meal.

What is there to do in San Gimignano during the free time?

San Gimignano is known for its 14 medieval towers built by wealthy families centuries ago as symbols of power. You can climb to the top of some towers for views of the surrounding countryside, walk the medieval streets, and visit the Basilica of Santa Maria Assunta during your free time in town.

How long is the tour, and what time does it end?

The tour lasts about 6 hours. If you depart from Tuscany on Wheels, it ends around 4:30 pm. If you depart from San Gimignano, it ends around 2:30 pm and you stay in town instead of returning to the office.

Do I need to be a wine expert to enjoy this tour?

No. The winemakers and guide teach you to recognize different flavors and refine your palate as you taste, so new skills are part of the experience. The tour is suitable for all physical fitness levels, and you must be at least 18 years old.