Chianti and San Gimignano Sunset Tour from Siena

Taste Chianti in the cellars, then dine at sunset overlooking San Gimignano's towers

A small-group afternoon and evening tour from Siena that takes you through the Chianti countryside to a working winery for cellar tour and Black Rooster Classico tasting, then to the medieval hilltop town of San Gimignano as the day crowds thin, and finishes with a farm-to-table dinner of local products and wine at a rustic farmhouse overlooking the towers and rolling vine-covered hills. The tour runs about eight to nine hours and includes professional English-speaking guide, air-conditioned minivan transport, the winery visit with tasting, and the traditional Tuscan dinner. Entrance fees to San Gimignano's churches and museums are at your own expense.

Step-by-step itinerary

Stops and time spent at each

1. Basilica of San Domenicopassing by
2. Basilica of Santa Maria Assunta1h

Chianti and San Gimignano sunset tour

• Meet guide at San Domenico church
• Drive through Chianti countryside
• Visit Chianti wine estate and tour cellars
• Taste Black Rooster Chianti Classico wine
• Visit medieval town Monteriggioni
• Explore Monteriggioni streets and shops
• Arrive in San Gimignano at late afternoon
• Free time to visit church or museum
• Shop artisan boutiques and food shops
• Dine at rustic farmhouse with wine

The experience

You meet your guide at 2:30pm in front of the Basilica of San Domenico in Siena and drive through the Chianti region. Dense oak forests and cypress trees give way to vineyards as you approach a local wine estate. There you tour the cellars, learn how the wine is made, and sit down to taste Black Rooster Chianti Classico. The winery visit anchors the afternoon. Everything after it moves toward the sunset dinner.

On the way to San Gimignano, you stop in Monteriggioni, a perfectly preserved medieval fortress town with a complete ring of walls and turrets still standing. It's a quiet hamlet now, and you have leisure time to walk the charming streets and browse local craft shops. Then you arrive in San Gimignano in the late afternoon as the crowds begin to thin. The town's famous medieval towers (it once flourished as a stop on the via Francigena trade route) rise above the streets. You have free time to enter the Collegiata di San Gimignano church, explore the Civic Museum if you choose (entrance at your own cost), or wander the artisan boutiques selling leather goods and hand-painted pottery. Food shops and wine bars let you sample local products before dinner.

After San Gimignano, you head to a nearby rustic farmhouse for a classic Tuscan dinner of the farm's own products and wines. You eat with the others on the tour, and the farmhouse location overlooks the San Gimignano towers and the rolling, vine-covered hills as the light fades. Dinner is included. The whole experience closes around 10:30pm or later depending on the season.

What’s included

• Professional English-speaking guide.
• air-conditioned minivan transport from Siena.
• tour of a Chianti wine estate with cellar access and Black Rooster Chianti Classico tasting.
• leisure time in the medieval fortress town of Monteriggioni.
• free time to explore San Gimignano's streets, shops and churches (entrance fees to museums and churches at your own expense).
• traditional farm-to-table Tuscan dinner with the farm's wines at a rustic farmhouse overlooking San Gimignano and the Chianti hills.

Before you book

Days and timesNext departure: 3 Apr 2027

Book up toStart time

AgesAdult (3 and older) · Infant (under 3)

GroupUp to 8

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 2 days ago

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearbyNot recommended with heart problems

Operated by Tuscan Escapes by Papilio SRL

Is this one for you?The eight to nine hour span means you leave Siena mid-afternoon and return late evening, so this works best if your day is already free from morning plans and you don't have an early start the next morning. If you want to see Siena's main sights or spend time in the city center, plan that for the morning before the 2:30pm meeting.

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Top questions

Can children come?

Yes. Ticket types: Infant (under 3).

What is the Black Rooster Chianti Classico wine I'll taste at the winery?

Black Rooster Chianti Classico is the traditional wine of the Chianti region, marked by the Gallo Nero (black rooster) symbol on the bottle. At the estate, you'll taste it after touring the cellars and learning how it's made from the local grapes and methods.

Can I visit the inside of San Gimignano's churches and museums, or do I just walk the streets?

You have free time in San Gimignano to enter the Collegiata di San Gimignano church or explore the Civic Museum if you wish, but entrance fees are at your own expense. Many travelers also browse the artisan shops, food stores and wine bars, or simply walk the medieval streets and squares.

What time does the farm dinner start and how late does the tour run?

The farm dinner begins after you leave San Gimignano in the late afternoon, and the tour typically ends around 10:30pm or later depending on the season and how long you linger over the meal and the views.

Is hotel pickup included, or do I meet the guide in Siena?

You meet your guide at 2:30pm in front of the Basilica of San Domenico in Siena. Hotel pickup and drop-off are not included. You'll need to arrange your own transport to the meeting point.

What does the farm dinner include, and is wine served with it?

The farm dinner is a traditional Tuscan meal made from the farm's own products, served with the farm's wines. The meal is included in the tour price and eaten communally with the other travelers on your group.