San Gimignano Chianti Montalcino Wine Tour with Tastings

Medieval towers, Tuscan countryside and two wines in one day

A full-day minivan tour from Siena through three Tuscan landmarks: San Gimignano (the City of Fine Towers), the Chianti wine region and Montalcino overlooking Brunello vineyards. You get free time to walk each town, two wine tastings at working wineries with guided tours, and transport by air-conditioned minivan for a maximum of eight people. A guide in English, Spanish or Italian provides commentary on the route and at the wineries.

Step-by-step itinerary

Stops and time spent at each

1. Montalcino2h
2. Montalcino Fortress1h

Tuscan countryside and wine tasting tour

• Meet at Via Giuseppe Garibaldi 72, Siena
• Travel by minivan to San Gimignano
• Free time to explore San Gimignano center
• Visit Cathedral of San Gimignano (optional)
• Visit Palazzo Pubblico and Big Tower (optional)
• Visit Piazza della Cisterna
• Wine tasting and optional lunch at Chianti winery
• Travel by minivan to Montalcino through Val d'Orcia
• Free time to explore Montalcino and fortress
• Visit winery and taste Brunello di Montalcino
• Return to Siena by minivan

The experience

The tour starts at Via Giuseppe Garibaldi in Siena and heads first to San Gimignano, where you have free time to explore the medieval center on your own. The town is known for its towers (some still standing from the 12th and 13th centuries), and the Cathedral of San Gimignano and Palazzo Pubblico are open for entry if you want to climb the Big Tower overlooking Piazza della Cisterna. After San Gimignano, the minivan carries you to a Chianti winery for a wine tasting and the chance to buy lunch on-site.

The route then moves south through Val d'Orcia, a UNESCO World Heritage Site since 2004, toward Montalcino. From the hilltop town you can see 1500 hectares of Brunello vineyards spreading across the landscape. You'll have free time to walk the cobblestone streets and visit Montalcino Fortress, where a 4-euro walkway on the walls overlooks the valley. The final stop is a local winery for a tasting of Brunello di Montalcino, one of Italy's top DOCG wines, along with typical local products. The minivan returns you to the same Siena meeting point after the full day.

The tour runs 11 hours total and accommodates a maximum of eight people per minivan, so the group stays small. Your guide speaks English, Spanish or Italian and travels with you throughout, offering insights on the drive and at each winery stop.

What’s included

• Expert multilingual guide in English, Spanish or Italian.
• two wine tastings with guided winery tours.
• minivan transport with air conditioning for up to eight people.
• hotel or meeting point pickup and return in Siena.

Before you book

Days and timesNext departure: 1 Apr 2027

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 yesterday

Good to know

Low physical effortStroller-friendlyPublic transport nearby

Operated by MyLuxuryDrive

Is this one for you?The guide speaks English, Spanish or Italian throughout the day, so you follow the commentary at each stop and during the drive. Groups stay under eight people per minivan, which keeps the pace relaxed and the winery tastings intimate rather than crowded.

Traveler reviews

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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 is San Gimignano known for?

San Gimignano is called the City of Fine Towers for its medieval towers that still rise from the town center. Many date to the 12th and 13th centuries. You have free time to walk the historical center, visit the Cathedral and Palazzo Pubblico, and explore Piazza della Cisterna, which features a beautiful medieval well.

Do I get to taste wine at both stops?

Yes. You taste Chianti at the first winery in the Chianti region, and Brunello di Montalcino at the second winery in the Val d'Orcia area. Both tastings include a guided tour of the winery, and at the Chianti stop you can also buy lunch if you want.

What is included in the tour price?

The tour includes transport by minivan with air conditioning, two wine tastings with guided tours at two wineries, and a multilingual guide in English, Spanish or Italian. Lunch is optional and costs extra at the Chianti winery.

Can I visit the Montalcino Fortress walls?

Yes. During your free time in Montalcino, you can walk the fortress walls for a 4-euro fee. The walkway overlooks Val d'Orcia and the Brunello vineyards. Entry times and prices are available at the fortress website.