Chianti wine tasting tour from San Gimignano: Two wineries

Two wineries, seven wines, and the Chianti Classico landscape in one morning

A small-group wine tour from San Gimignano visits two estates in the Chianti Classico region for seven tastings paired with local bread, salami, olive oil and balsamic vinegar. The tour lasts seven hours, includes an expert guide in English, Spanish or Italian, and travels by air-conditioned minivan or minibus depending on group size. A brief stop in Siena picks up additional participants before heading to the wineries.

Step-by-step itinerary

Chianti wine and village visits

• Visit first winery and wine tasting
• Explore Castellina in Chianti village
• Visit Monteriggioni village and take photos
• Visit second winery and wine tasting

The experience

The tour departs from San Gimignano and heads into the Chianti Classico area, where two wineries anchor the day. At each estate, you taste wines and walk the grounds with a guide who explains what you're drinking: the ruby-red color and violet aromas that define Chianti are not accidents of the soil, but choices the winemakers make. Seven wines in total across both tastings, paired with typical Tuscan food: bread, salami, olive oil and balsamic vinegar sampled on-site. The guide speaks English, Spanish or Italian depending on the group. Translation support is available when needed.

Between the two wineries, the route passes through Castellina in Chianti, a village in the heart of the region where you can walk its historic landmarks and taste local food, and Monteriggioni, an ancient fortified village where most travelers stop to photograph the stone walls and the surrounding landscape. The minivan or minibus is air-conditioned, and a moderate amount of stairs and walking is involved at the estates themselves. The itinerary may shift depending on seasonal events and winery hours, but all four stops (two wineries, Castellina and Monteriggioni) stay in the day.

Groups run small, up to eight people in a minivan or up to thirty in a minibus. A brief pickup stop in Siena happens before the wineries, so the route begins in San Gimignano but does not include a Siena visit. WiFi is available on board.

What’s included

• Two winery estate tours with seven wine tastings.
• Tuscan food pairings including bread, salami, olive oil and balsamic vinegar.
• expert multilingual guide.
• air-conditioned minivan or minibus transport.
• WiFi on board.
• stops in Castellina in Chianti and Monteriggioni village.

Options for this experience

2 options

Summer tourGuide in English, Spanish or Italian · 13:00Starting time during the summer season is 1:00 PM

Winter tourGuide in English, Spanish or Italian · Available from 17 Nov · 12:00During the winter season, the starting time is 12:00 PM

You pick the guide language when booking.

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

Before you book

Days and timesTuesday, Thursday and SaturdayDepartures at 12:00 and 13:00

Book up to12h before

AgesAdult (13 and older) · Child (3 to 12 years) · Infant (under 3): free

GroupUp to 30

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 3 days ago

Good to know

Low physical effort

Operated by myTour in Italy

Is this one for you?Small groups of up to eight travelers in a minivan or larger groups up to thirty in a minibus suit different party sizes. Choose the summer or winter departure based on when you visit Tuscany, as opening hours and seasonal events shift the exact timing of stops.

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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: Child (3 to 12 years); Infant (under 3): free.

How many wines do you taste on this tour?

Seven wines in total across the two winery visits, each tasting paired with Tuscan food and olive oil sampling.

What is Castellina in Chianti like to walk through?

Castellina is a charming village in the heart of Tuscany with historic landmarks, local cuisine and vineyard views surrounding it. Travelers explore on foot and can savor local food during the stop.

How long is the full tour?

Seven hours from start to finish, including travel time between San Gimignano, the two wineries, and the village stops.

Can I book this tour if I'm traveling alone or with one other person?

Yes. The tour runs year-round in both summer and winter versions. The Italian-language option requires a minimum of four participants, but English departures are guaranteed regardless of group size.