Small-Group Chianti and San Gimignano Sunset Trip from Siena

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine by visiting a local producer, touring their cellars and tasting their wines. Then head to the UNESCO World Heritage town of San Gimignano, famous for its medieval towers. Enjoy the main sights and browse the streets and boutique stores just as the day's crowds begin to dwindle. Visit a local farm and enjoy a farm-to-table dinner of its products and wines during sunset, in a stunning location overlooking the San Gimignano towers and the rolling, vine-covered hills.

1. 1

   Basilica Cateriniana Di S. Domenico

   Pass by

   Meet your tour guide at 2.30pm in front of the church of San Domenico in Siena and begin the tour with a comfortable drive through the Chianti countryside. Visit a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the wine-making process. Sit down and savor a tasting of Black Rooster Chianti Classico wine.

2. 2

   Cantinetta di Monteriggioni

   30 min

   After visiting a Chianti winery, visit a historic town that was once of fortress, Monteriggioni, to marvel at the medieval towers that are still intact. Monteriggioni is a perfectly preserved medieval town with a complete ring of walls and turrets, once Siena’s main bastion of defense against the armies of Florence. Today it is a quiet hamlet and you can enjoy leisure time exploring the charming streets and stores of local crafts.

3. 3

   Historic Centre of San Gimignano

   1 hour

   In the late afternoon, arrive in San Gimignano as the crowds begin to dwindle and the many streets and squares of this medieval town of towers that flourished thanks to the via Francigena, an important trade route. Enjoy free time to enter its impressive church, the Collegiata di San Gimignano, or to explore the Civic Museum (entrance fees at own expense). Alternatively, shop the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars or discover the town’s many hidden beauties.

4. 4

   Strada Statale 222 Chiantigiana

   2 hours

   After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner accompanied by wine. Enjoy the farm's products and wine over a convivial dinner with the others on tour that you can now call new friends.

• Infants and small children can ride in a pram or stroller
• Public transportation options are available nearby
• Specialized infant seats are available
• Not recommended for travelers with poor cardiovascular health
• Suitable for all physical fitness levels
• Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol

For a full refund, cancel at least 24 hours before the scheduled departure time.