Full-Day Tuscany Day Trip from Siena with Wine Tasting

Explore the Tuscan countryside and go wine tasting with a leading expert
From US$2,453 privately
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Tour Details
8 hours
Product Type
  • Pienza
  • Montalcino
  • Abbey of Sant'Antimo
  • Local Winery
Photos & Highlights
  • Join an engaging, local expert at the top of their field as you explore the Tuscan countryside and go wine tasting in the Val D'Orcia region
  • Unique, personal tours for the intentional traveler. Choose from private tours for just you and your party, or join a small group tour with other travelers
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Tour Description
This is a full-day excursion from Siena to the Val, d’Orcia, a UNESCO world heritage site with beautiful nature, picturesque hilltop towns and world-renowned vineyards. Traveling by private car and in the company of a local expert in history, art, and culture, this tour covers both the artistic and gastronomic highlights of the area. Tour Medieval and Renaissance hill towns, experience wine tasting at a Brunello di Montalcino winery and enjoy locally produced cheeses, all while taking in spectacular panoramas along the way.  

You will travel together with your guide by private van to get off the beaten path and into the heart of one of the most scenic areas of central Italy. On your drive, you will learn about the origins of the region - a UNESCO World Heritage site since 2004 - and the nearby Via Francigena. You will stop and visit Pienza, a renaissance gem of urban planning and city design whose classical origins inspired the template of cities all over Italy and, by extension, the world. While exploring the charming town, you will sample delicious locally produced sheep's milk or pecorino cheeses.  

Afterward, you will travel through the stunning countryside to Montalcino, a medieval village of ancient origins. Surrounded by fortified walls, this tiny stronghold was once a leather-making center of Tuscany and is now most famous for the vineyards beyond its borders. After a walk around the town center, you will sit down for a local lunch in a trattoria with your guide.  

After lunch, you will make your way to the Abbey of Sant’Antimo, a twelfth-century Benedictine monastery with eighth-century roots. In the peaceful surrounds of the Tuscan hills, your guide will unfold this chapter of Italian history for us. You will complete your day with a visit to a local winery to see the operation and have a tasting while learning about the classification of Italian wines and understand the climatic conditions necessary to produce the Sangiovese grapes integral to Brunello wines.
  • You're a photography enthusiast seeking picturesque landscapes and photo-worthy moments without an overnight stay
  • You like to indulge your passion for food and wine, embarking on a culinary journey through tantalizing local delights
  • You want to sit back, relax, and allow our team to handle all the transportation details – ensuring you reach your destination hassle-free and return with ease
  • Pienza – hill town known for its Renaissance architecture in the Val d'Orcia.
  • Local trattoria in Montalcino – casual restaurant serving authentic Tuscan cuisine. 
  • Abbey of Sant'Antimo – twelfth-century abbey of Romanesque architectural style located in the Montalcino region.
  • Montalcino winery – Tuscan winery specializing in the red wine production made exclusively from Sangiovese grapes.
  • This tour includes a private car service that will pick you up at your accommodation in Siena, will drive you to the different sites visited in Val D'Orcia, and will drop you off at your accommodation in Siena at the end of the tour.
  • The tour will take time for a lunch break at a local trattoria, but you are responsible for the cost of your own lunch.
  • You are prepaid for the cost of the wine tastings, however, please keep in mind that you are responsible for the cost of the Pecorino cheese tastings, as the cost may vary depending on your taste. 
  • The itinerary is adaptable for clients with mobility issues.
Wheelchair accessibility
  • Most of the sites are wheelchair accessible. 
  • If you have mobility concerns, please contact us to discuss the best tour option for you
For more information about Context Tours, please visit our FAQs.

What if I am not staying in Siena? 
The tour is exclusively for departure from Siena. If you’re staying in Florence, please take a look at Full-Day Tuscany Day Trip from Florence with Wine Tasting.   
Book with confidence — see Context's flexible cancellation policy here.
Where You'll Start
(4.47) 3 Reviews

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

Alessandra was absolutely wonderful! Extremely knowledgeable.. a perfect tour!
It was too hard to get information from you. Like what winery we were going to, what restaurant, etc. This comment is in addition to my comment about the two vans and why I would never choose to travel with you again.
We were a family of 9 people. There was absolutely no reason we had to be in 2 vans with 2 guides and charged the full amount twice. I feel that was gouging. We had other tours where we were all in the same van.