Chianti wine tasting from Siena: Two family wineries

Two Chianti wineries, seven wines, and a medieval village in one afternoon

A small-group wine tasting tour from Siena visits two family-run wineries in the Chianti region, where you taste seven wines paired with bruschetta, salami, cheese and olive oil. Between tastings, you have free time in Castellina in Chianti and the walled village of Monteriggioni to walk, photograph or rest before returning to Siena by minivan.

Step-by-step itinerary

Chianti wine tastings and village visits

• Meet staff at Siena Station
• Travel by minivan to winery
• Wine tasting with bruschetta and olive oil
• Free time in Castellina in Chianti
• Second wine and local products tasting
• Free time in Monteriggioni village
• Return to Siena

The experience

You meet your guide at Siena Railway Station in front of the clock tower, then travel by air-conditioned minivan through rolling vineyards to the first winery. The tasting there covers three wines with bruschetta, bread and olive oil: a straightforward introduction to how the region's producers work. After that first stop, you have free time in Castellina in Chianti, a village surrounded by vines where you can walk, grab a coffee or simply sit and look at the landscape.

The second winery brings another round of Tuscan wines, olive oil and local products. Across both tastings, you sample seven wines in total, each paired with the food that goes with it. Your guide speaks English and provides translation support in Spanish or Italian when needed, so the winemakers' explanations come through clearly. A moderate amount of stairs and walking is involved at both estates, and the itinerary can shift depending on what the wineries have open on the day you visit, but all the stops happen regardless.

On the drive back to Siena, you stop in Monteriggioni, a medieval walled village perched on a hilltop. The walls and narrow streets are built to photograph well, and there are local shops if you want to pick something up. You have time to wander before heading back to the station, where the tour ends after roughly five hours away from the city.

What’s included

• Tasting of seven wines across two family-run wineries.
• bruschetta, salami, cheese and extra virgin olive oil.
• expert multilingual guide and driver.
• air-conditioned minivan transport.
• free time in Castellina in Chianti and Monteriggioni.

Options for this experience

3 options

Budget Chianti half-day tourGuide in English, Spanish or Italian · 14:00Budget Chianti half-day tour at 2:00 pm: 3 glasses of wine and snacks

Premium Chianti half-day tour at 1:00 pmGuide in English, Spanish or Italian · Available from 17 Nov · 13:00Small-group Chianti and castle tour from Siena at 1:00 pm, with 7 wines

Premium Chianti half-day tourGuide in English, Spanish or Italian · 14:00Small-group Chianti and castle tour from Siena at 2:00 pm, with 7 wines

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 13:00 and 14:00

Book up to10h before

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

GroupUp to 29

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.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 effortStroller-friendlyInfant seats availablePublic transport nearbyInfants must sit on laps

Operated by myTour in Italy

Is this one for you?Groups stay small (up to eight in a minivan or up to thirty in a minibus), so the pace at each winery stays unhurried and the guide can answer questions without rushing through the tastings. The two stops for free time let you set your own rhythm between the wine experiences rather than moving straight from one tasting to the next.

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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.

What exactly do I taste at the two Chianti wineries?

You taste seven wines in total across both wineries, paired with bruschetta, bread, olive oil, salami and cheese. The first winery covers three wines with bruschetta and bread. The second features Tuscan wines, olive oil and local products.

Is there time to explore Monteriggioni, or is it just a quick stop?

Monteriggioni is a free-time stop on the way back to Siena, so you have room to walk the medieval walled village, take photographs of the Tuscan landscape and visit local shops before the tour ends.

How much walking and climbing is involved in this tour?

A moderate amount of stairs and walking is involved, particularly at the two wineries where the tastings take place. You should be comfortable climbing and descending stairs to move through the estates.

Do I need to arrange my own transport to Siena Railway Station?

You meet the staff at Siena Railway Station in front of the clock tower at the main entrance, where they wear green shirts. Public transportation options are available nearby if you need to reach the station.