Full-Day Tuscany Day Trip from Florence with Wine Tasting

Explore the picturesque towns of the Tuscany countryside and taste local wine
From US$2,032 privately
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Tour Details
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
Embark on a transcendent journey through the Val d'Orcia, a Tuscan tapestry of emerald hills, cypress groves, and medieval charm, renowned for its exquisite wines and cheeses. Under the azure Tuscan sky, your senses will awaken as you wind through the picturesque countryside, marveling at the rolling hills, ancient villages, and iconic cypress trees that grace this idyllic valley.

You will travel by car to Pienza, a Renaissance gem perched atop a hilltop, you'll savor the flavors of the region, savoring artisanal pecorinos at charming boutiques. Along with your local expert guide, you'll visit the Renaissance-style Duomo and city center, tasting various local pecorinos at small boutique food shops.

Next, you will quench your thirst in Montalcino, a world-renowned wine town. You'll enjoy a light lunch at a traditional enoteca, where local cheeses, salami, and wines await. In the afternoon, the abbey of Sant'Antimo awaits, its ancient stones whispering tales of faith and history. From here, you'll get an in-depth look at the local wine scene with a visit to a Montalcino winery, where you will indulge in samples of the highly-regarded Brunello wine and learn about its history and production. 

As the sun casts its golden glow over the Tuscan hills, you will be driven back to your accommodation, sated by both appreciation for the region's culinary traditions and the tastings.
  • 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 Florence, will drive you to the different sites visited in Val D'Orcia, and will drop you off at your accommodation in Florence 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 Florence? 
The tour is exclusively for departure from Florence. If you’re staying in Siena, please take a look at Full-Day Tuscany Day Trip from Siena with Wine Tasting.   
Book with confidence — see Context's flexible cancellation policy here.

Where You'll Start
(4.96) 18 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.

Stella was excellent and knowledgeable guide during our Tuscany trip. I loved the itinerary and her stories of the area.
Stella was kind to work with us as we were driving from Florence to Sinalunga. We met in Pienza and were about 35 minutes late due to a bit of a mixup with both the rental cr company (slow) and travel directions. Still, she was gracious and it did not impact the day negatively. We enjoyed every aspect: Pienza, Montalcino, Abbey Sant'Antimo, the Prima Donnne winery tour and tasting. Stella is knowledgable and delightful, a thoroughly welcoming and kind host guide. The driver Stefano was professional and helpful.
We had a lovely time driving through the Tuscan countryside. Pienza was marvelous and what great cheeses. I regret I didn't take a couple of photos inside the wonderful cheese shops. What made our day even more fun was our side trip to Monticchiello to visit the theatre museum there. For a small village (at least by American terms) it had a fantastic museum. It was so kind of museum folks to open the theatre for us to visit. Being theatre people we thoroughly enjoyed that. My husband still talks of the wonderful meal we had in Monticchiello. He still declares that to be the best pasta he has ever had. My only negative thing I can say about any of our tours and this had nothing to do with Stella or Context was that I felt the people at the Barbi winery just could not be bothered by our business. In fact I think the gentleman who was doing our tasting would have preferred us to just leave. Stella, however, made up for that gentlemen's attitude by taking us to the enoteca at La Fortezza Di Montalcino where we had a delightful tasting with Jo who clearly was willing to take his time with us, chat with us and explain whatever we needed explaining.. And I must compliment Stefano, our driver. I have no idea how he managed to manuever the van through the small streets of Monticchiello. But he did so graciously and calmly. Our drive to Firenze was smooth and uneventful. He was most kind. Please also give our very best to Stella and Stefano