Stella was a wonderful guide. She knew the area well and showed up some fabulous sights. Wine tasting was fun, and we learned so much. Thanks for a fantastic experience Stella!
Val d’Orcia Day Trip from Siena: Pienza and Wine
Taste Brunello and Pecorino in Tuscany’s hill towns
The Finer Details
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.
In the peaceful surroundings of the Tuscan hills, your guide will unfold this chapter of Italian history for you. 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 understanding the climatic conditions necessary to produce the Sangiovese grapes integral to Brunello wines.
Choose this tour if...
- 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
Sites Visited
- Pienza – hill town known for its Renaissance architecture in the Val d'Orcia.
- Local trattoria in Montalcino – casual restaurant serving authentic Tuscan cuisine.
- Montalcino winery – Tuscan winery specializing in the red wine production made exclusively from Sangiovese grapes.
Logistics
Transportation
- This tour includes a private car service that will pick you up at your accommodation in Siena, drive you to the different sites visited in Val D'Orcia, and drop you off at your accommodation in Siena at the end of the tour.
Lunch
- The tour will take time for a lunch break at a local trattoria, but you are responsible for the cost of your own lunch.
Tastings
- 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.
Resources
- Check out our upcoming lectures on Tuscany to prepare for your trip.
Accessibility
Itinerary
- 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
Frequently Asked Questions
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.
Cancellation Policy
Book with confidence — see Context's flexible cancellation policy here.
Meet the Experts
Where You’ll Go
From iconic landmarks to tucked-away local favorites, these are the places you’ll explore and experience firsthand with your Expert.
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Pienza
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Montalcino
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Abbey of Sant'Antimo
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Local Winery
What’s Included As Standard
Here’s a look at what your tour covers, plus anything you’ll want to consider arranging separately, so you can plan with confidence.
Included
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English-speaking expert guideTours led in English, offering you unbroken understanding throughout.
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Intentionally sized groupsA smaller group means more time for conversations and questions.
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Tickets and entrance feesAll entry tickets included (unless clearly stated otherwise).
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HeadsetsHeadsets are included on tours that need them, so every word can be heard.
Not Included
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Food and drinkUnless booking a Food & Drink tour or tasting experience, refreshments are not included.
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Transportation to and from the meeting pointUnless noted, pre- and post-tour transport isn’t included - this service can be added by request.
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GratuitiesTips aren’t included, but we encourage tipping as a way to thank your guide after your experience.
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Hotel pickup or drop-offUnless noted, travel to or from accommodation isn’t included - this service can be added by request.
Make the Most of Your Tour
Some helpful advice for getting the most from your experience, from practical prep to small on-the-day tips.
Dos:
- Wear comfortable footwear
- Check the weather and dress appropriately
- Bring a bottle of water (no glass)
- Feel free to ask your Expert anything
Don'ts:
- Bring firearms or weapons
- Bring sharp objects (e.g. knives, swiss army knives, switchblades, hiking sticks)
- Dress inappropriately to enter religious sites or sacred monuments
Any questions? You can always
contact us.
Don’t just take our word for it
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.
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