Full-Day Tuscany Day Trip from Siena with Wine Tasting

Walking Tour

8 hrs

Siena

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 surroundings 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 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.
Abbey of Sant'Antimo – a 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.

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.

Book a Tour

From iconic landmarks to tucked-away local favorites, these are the places you’ll explore and experience firsthand with your Expert.

Pienza
Montalcino
Abbey of Sant'Antimo
Local Winery

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

English-speaking expert guide
Tours led in English, offering you unbroken understanding throughout.
Intentionally sized groups
A smaller group means more time for conversations and questions.
Tickets and entrance fees
All entry tickets included (unless clearly stated otherwise).
Headsets
Headsets are included on tours that need them, so every word can be heard.

Excluded

Gratuities

We encourage tipping as a way to thank your guide after your experience.
Food and drink

Refreshments are only included during a tour when clearly noted.
Transportation to and from the meeting point

Guests organize pre- and post-tour transport themselves - this service can be added by request.
Hotel pickup or drop-off

Unless noted, travel to or from accommodation isn’t included - this service can be added by request.

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.

6 Reviews

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!

Cathy Jul 30, 2025

Alessandra was absolutely wonderful! Extremely knowledgeable.. a perfect tour!

Maria Oct 12, 2023

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.

Corinne Jun 30, 2022

Join passionate experts on intimate walking tours that reveal a city’s unique stories, spark conversations, and leave you seeing the world—and yourself—a little differently.

Structured, never scripted

Your interests guide your Expert, leading to stories and perspectives that matter to you.

Crafted for conversation

With ten or fewer guests, ask questions, engage with your Expert, and fully immerse yourself.

Experts, not guides

Explore with 1,200+ Experts—from historians and architects to archaeologists and chefs.