Chianti and Castles Tour from San Gimignano: Two Wineries

Taste Chianti at two wineries while walking medieval villages built to rival Florence

A half-day small-group tour from San Gimignano through Chianti wine country, visiting the 15th-century village of Castellina in Chianti and the walled medieval fortress of Monteriggioni, with wine tastings at two estates. The minivan departs from Porta San Giovanni. A multilingual guide travels with the group and provides commentary during the drive between stops.

Step-by-step itinerary

Chianti and Castles Half-Day Tour

• Start trip from San Gimignano
• Travel to Castellina in Chianti
• Visit Castellina in Chianti village
• Wine tasting at Chianti winery
• Stroll around Monteriggioni village
• Wine tasting near Monteriggioni
• Return to San Gimignano

The experience

You leave San Gimignano from Porta San Giovanni in an air-conditioned minivan and head into the Chianti hills. The driver offers information about the landscape as you travel to Castellina in Chianti, where you have free time to explore on your own. The town centers on the Rocca, a 15th-century tower with a keep that opens onto views across the Tuscan hills, and the Church of San Salvatore, rebuilt in neo-Romanesque style after World War II damage. Covered streets wind through the old town with workshops, restaurants and secret passages overlooking the countryside.

Wine tasting happens at two separate estates. At the first winery in the Chianti area, you taste the region's signature wine: a blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes. The ruby-red color and violet-tinged aroma are what distinguish Chianti from other Italian wines. At the second estate near Monteriggioni, you sample wines from a quality cellar in a landscape the operator describes as magical and pleasant. Both tastings include oil and balsamic vinegar alongside the wine.

Between the two wineries, you stroll around Monteriggioni, a walled village founded in the early 13th century by the Republic of Siena to defend against Florence. The castle walls and layout remain intact from that medieval rivalry. After the second tasting, the minivan returns you to Porta San Giovanni in San Gimignano.

What’s included

• Visit to Castellina in Chianti with free time to explore the 15th-century Rocca and Church of San Salvatore.
• stroll around the walled medieval village of Monteriggioni.
• wine, oil and balsamic vinegar tastings at two separate estates in the Chianti area.
• travel by air-conditioned minivan.
• expert multilingual guide in English, Spanish or Italian.

Options for this experience

2 options

Small Group Chianti and Castles Tour from San GimignanoGuide in English, Spanish or Italian · 13:00

WINTERGuide in English, Spanish or Italian · Available from 17 Nov · 00:00

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 timesEvery dayDeparts at 13:00

Book up to12h before

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

GroupUp to 8

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 2 days ago

Good to know

Low physical effortStroller-friendlyPublic transport nearby

Operated by MyLuxuryDrive

Is this one for you?Book this if you have a free afternoon and want to compare two different Chianti estates rather than taste at just one location.

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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 is Chianti wine and what grapes go into it?

Chianti is a red wine blend made from Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes grown in the Chianti region. The wine is known for its ruby-red color and aroma with hints of violet.

Can I visit Castellina in Chianti and Monteriggioni on my own, or does the guide lead the whole tour?

You have free time to explore Castellina in Chianti at your own pace. Monteriggioni is a stroll the group takes together. The guide travels with you in the minivan between stops and provides commentary during the drive.

What's included in the wine tastings at the two estates?

Both tastings include wine, oil and balsamic vinegar. The first estate focuses on Chianti wine. The second is a quality cellar with a range of wines from the area.

Is this tour suitable for someone visiting Tuscany for the first time?

Yes. The tour covers two of Chianti's most recognizable villages and includes two wine tastings, giving a solid introduction to the region's landscape, history and wine. The minivan travel means you see the countryside between stops without arranging your own transport.