Montepulciano, Pienza, and the Essence of Val d’Orcia

Discover Tuscany's highlights on this private 10-11 hour tour from Florence, featuring Montepulciano, Pienza, and the scenic Val d'Orcia with expert guides.

Explore Tuscany’s Charm with a Private Val d’Orcia Tour from Florence

This full-day private tour costs $675.27 per person and lasts approximately 10 to 11 hours. Starting from Florence or other Tuscan locations, it offers an intimate and flexible way to experience some of Tuscany’s most celebrated sights. Guided by expert local drivers, the tour combines cultural visits, wine tasting, and breathtaking landscapes, making it ideal for those seeking a curated taste of the region’s heritage and flavors.

With pickup offered, group discounts, and a mobile ticket, it presents a convenient and personalized experience. The tour’s high rating of 5.0 from 1 review reflects strong satisfaction, especially with its carefully selected stops and authentic experiences. While it is a premium offering, the inclusion of private transportation and a light lunch with wine tasting enhances its value. It suits travelers eager to uncover Tuscany’s hidden corners without the hassle of self-driving or rigid schedules.

Key Points

  • Private, flexible 10-11 hour tour from Florence or other Tuscan locations
  • Includes guided visits to Montepulciano, Pienza, and Bagno Vignoni
  • Wine tasting at De’ Ricci Cantine Storiche with at least 4 wines
  • Delicious light lunch in a historic Montepulciano cellar, customizable for dietary needs
  • Scenic stops at Vitaleta Chapel, Monticchiello, and the thermal waters of Bagno Vignoni
  • Perfect for travelers seeking an intimate, curated Tuscan experience with expert guides

Starting Point and Transportation Details

This tour departs at 9:00 am with private transportation in an air-conditioned vehicle. Pickup options simplify logistics, and the private nature of the tour means only your group participates, allowing for personalized pacing and flexibility. The vehicle’s comfort ensures a smooth journey through Tuscany’s rolling hills, passing small towns and picturesque landscapes en route to the region’s highlights.

Discovering Montepulciano’s Medieval and Wine Heritage

The first stop is the Piazza Grande in Montepulciano, a hub of medieval and Renaissance architecture. This 45-minute visit offers a chance to walk through the historic streets and enjoy views of the surrounding vineyards. Montepulciano is renowned for its Vino Nobile di Montepulciano, which you will taste during the included visit to De’ Ricci Cantine Storiche.

The caves at De’ Ricci provide a fascinating glimpse into the underground wine cellars, dug into the tuff stone over millennia. The 1 hour and 30 minutes spent here include a wine tasting of at least 4 different wines, giving a genuine feel for the region’s winemaking tradition. The guides are known for explaining the history and craftsmanship behind each glass, adding depth to the experience.

Enjoying a Classic Italian Espresso in Montepulciano

After exploring Montepulciano, the tour offers a 30-minute break at Caffè Poliziano, a historic café within the medieval city. This free time allows for wandering the alleys, soaking in the ambiance, and sampling an authentic Italian espresso. It provides a moment of relaxation and a chance to absorb the city’s atmosphere at your own pace.

Tasting Tuscany’s Famous Pecorino Cheese in Pienza

Traveling onwards, the tour makes a 15-minute stop at Cugusi Silvana E C. S.N.C., an internationally recognized producer of Pecorino cheese. This visit offers a quick but insightful look into one of Tuscany’s most celebrated dairy traditions. The dairy is highly awarded, and the stop is free of charge, providing an opportunity to learn about the cheese-making process and sample local varieties.

Next, the tour visits Pienza, a UNESCO World Heritage Site designed by Pope Pius II as the “ideal city.” A 1-hour walk takes in its elegant streets, panoramic views, and Renaissance architecture. This charming town is famous for its delicious Pecorino cheese, complementing the region’s culinary reputation.

Capturing Photos of Tuscany’s Iconic Landscape

The Chapel Vitaleta is a highlight for photography lovers. Set amid golden fields and cypress-lined hills, this 10-minute stop offers a chance to photograph one of Tuscany’s most iconic landmarks. Its solitary presence in the landscape makes for stunning images and a moment of serenity during the busy day.

Exploring Monticchiello and Its Medieval Charm

Perched on a hilltop, Monticchiello offers a 30-minute walk through its ancient stone-walled streets. This small village provides a glimpse of traditional Tuscan life, with views over the Val d’Orcia’s rolling hills. Its quiet, unspoiled ambiance is perfect for appreciating Tuscany’s rural beauty away from crowded tourist spots.

Relaxing in the Thermal Waters of Bagno Vignoni

The final stop is Bagno Vignoni, famed for its historic thermal waters. Instead of a typical piazza, the village features a large, steaming thermal pool that has been used since Roman times. The 30-minute visit allows for a leisurely look at this unique feature and appreciation of its thermal charm.

Included Experiences and Practical Details

The tour’s price includes private transportation, an air-conditioned vehicle, and a light lunch in a historic Montepulciano cellar. The meal features wine tasting of at least 4 wines, with options to accommodate vegetarian, vegan, gluten-free, and minors menus upon request.

Meeting at 9:00 am, the tour offers flexibility with free cancellation up to 24 hours before. As a private tour, only your group participates, ensuring personalized attention and a relaxed pace. Service animals are allowed, making this accessible for more travelers.

Why this Tour Stands Out

The combination of stops on this tour covers both cultural and natural highlights, from Medieval towns and Renaissance architecture to breathtaking landscapes and thermal springs. The focus on authentic experiences, such as wine tasting and visiting award-winning cheese producers, makes it particularly appealing for food and wine lovers.

The expert guides bring the region’s stories alive, and the flexible itinerary allows some adjustment based on preferences. The inclusion of local drivers enhances comfort and efficiency, allowing travelers to focus on what truly matters: enjoying Tuscany’s beauty.

Who Will Love This Tour Most

This experience is ideal for visitors who want a personalized, in-depth look at Tuscany’s treasures without the constraints of a large group. It suits those interested in wine, cheese, and scenic landscapes and who appreciate a culturally rich yet relaxed day. The long, well-paced itinerary ensures meaningful visits without feeling rushed.

Final Thoughts on the Montepulciano, Pienza, and Val d’Orcia Tour

At $675.27 per person, this tour offers a luxury experience in Tuscany, blending cultural sightseeing, wine tasting, and stunning vistas. Its high rating and positive features suggest it appeals to discerning travelers who seek quality and authenticity.

While it is a premium offering, the inclusion of private transport and customizable menus adds value for those wanting a tailored experience. It’s especially suited for visitors ready to explore Tuscany’s hidden corners with comfort and expert guidance.

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Montepulciano, Pienza, and the Essence of Val d’Orcia



5.0

100% 5-star

“Wrapping up a 3 week trip to Tuscany for the celebration of our daughter's wedding. As a extension, we planned some tours through Tours in Tuscany….”

— A Tripadvisor Reviewer, Aug 2025

Frequently Asked Questions

What is included in the tour price?
The price covers private transportation, an air-conditioned vehicle, a light lunch, and wine tasting of at least 4 wines. The stop at the Pecorino cheese producer and visits to towns are also included.

How long does the tour last?
The tour lasts approximately 10 to 11 hours, starting at 9:00 am. It offers a full day of exploring Tuscany’s highlights at a relaxed pace.

Is the tour suitable for dietary restrictions?
Yes, the lunch menus can be tailored for vegetarian, vegan, gluten-free diets, and minors, upon request.

What are the main stops on the tour?
Stops include Montepulciano, De’ Ricci Cantine Storiche for wine tasting, Pienza, the Vitaleta Chapel, Monticchiello, and Bagno Vignoni thermal waters.

Can I cancel the tour?
Yes, free cancellation is available up to 24 hours before the scheduled start time.

Is this tour suitable for children or service animals?
Yes, service animals are permitted, and the tour can accommodate most travelers, making it accessible for families and individuals with needs.