Full-Day Tuscany Day Trip from Florence with Wine Tasting

Explore the picturesque towns of the Tuscany countryside and taste local wine
From US$2,038 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.

Great way to see the Tuscany landscape and appreciate the Brunello wines.
Lovely trip! Stella is amazing and Alessandro a perfect driver!
Driver and guide were excellent. She reorganized a few things on the fly and made trip that much better. The small towns we visited and stopping along the road to step out and take pics were awesome. The restaurant overlooking the valley was great and winery was a nice final stop. Great Day!