Eyes of Rome
Eyes of Rome

Day Trip from Florence: Pienza and Montalcino

Tuscany's Jewels: Historic Pienza and Enchanting Montalcino


  • Food&Wine
  • Nature
  • Art
  • History

What makes this tour Special

Uncover the rich historical tapestry of Pienza and Montalcino, guided by experts.

Immerse in the breathtaking Tuscan landscapes of Val d'Orcia, a UNESCO World Heritage site.

Savor the exquisite flavors of Brunello wines, deepening your appreciation for Tuscan viniculture.

What to Expect


Enjoy your tour with your own private tour expert at your party's disposal only


7 hours




Meet&Greet at your hotel/accomodation. Private Driver included throughout the tour


This tour is suitable for kids of all ages


Please don't forget to inform the guide in case of food intolerances or special dietary restrictions before the tour starts.

What's Included
  • Private Tour with a Driver Guide
  • Pick-up and drop-off at your accommodation
  • Free time in Montalcino
  • Winery visit with Brunello Tasting
  • Typical Tuscan Lunch
  • Free time in Pienza
  • Cheese tasting
Not Included/ Optional Extras
  • Additional beverages

Sites you’ll visit

  • Tuscan Hills
  • Montalcino
  • Montalcino Wine Tasting
  • Pienza
  • The famous countryside hills of Tuscany seem to be handmade as they perfectly slide one after the other into the distance. This setting also makes it the motherland of real Italian wine. Some of the most prestigious Red wines in the world come from these hills!
  • Located in the picturesque Tuscan countryside, wine tasting in Montalcino is a sensory and cultural enrichment. Renowned for its Brunello di Montalcino, one of Italy's most celebrated wines, Montalcino offers visitors a sublime experience. Ancient vineyards and historic wineries cater to aficionados and novices alike, sharing traditional winemaking methods and hosting tastings. While savoring the Brunello's rich complexity, the sweeping views of vineyards and olive groves complete the experience. Montalcino's wine tasting is a deep dive into the sublime elegance of Tuscan viticulture.
  • A wine-tasting experience in a local Montalcino winery is a cherished encounter with authentic Tuscan culture. Here, visitors delve into the old-world charm of local winemaking traditions, exploring rustic cellars once the stage for crafting world-acclaimed Brunello di Montalcino. In the intimate setting of a family-owned estate, you are invited to partake in the slow-paced pleasure of wine discovery—an unhurried indulgence of the senses traversing the nuanced flavors, rich aromas, and vibrant colors of the wine. Backed by generations of winemaking knowledge, the local vintners wholeheartedly share fascinating vineyard tales and wine secrets, making the Montalcino wine tasting a truly memorable and personal Tuscan experience.
  • Pienza, a jewel in Tuscany, is a remarkably preserved Renaissance town. Renowned for charming streets, breathtaking landscapes, and historic monuments, it's an epitome of Italian elegance. An equally famous attraction is its exquisite pecorino cheese, deeply embedded in local culture.

Tour description

Embark on a day-long journey from Florence to the enchanting towns of Pienza and Montalcino, nestled in the heart of Tuscany. This tour invites you to discover the picturesque landscapes and rich history of these renowned regions.

Your tour starts in Pienza, the "Ideal City of the Renaissance." As you meander through its beautifully planned streets, you'll be captivated by the town's harmonious architecture and the serene atmosphere of Piazza Pio II, a UNESCO World Heritage site. Pienza is a testament to Renaissance humanism, offering a window into a visionary past.

Traveling through the stunning Val d'Orcia, you'll be surrounded by a landscape that's a living painting. Admire the undulating hills, dotted with vineyards, olive groves, and iconic cypress trees — a scene that has inspired countless artists and writers.

In Montalcino, renowned for its Brunello di Montalcino wine, experience the town's medieval charm. Visit the imposing Montalcino Fortress for breathtaking views and stroll the ancient streets. The highlight is a visit to a local winery where you'll indulge in a Brunello wine tasting, understanding why this region is celebrated for its viniculture.

Useful information

Please let us know if you have any food allergies or requests

Full Refund Cancellation Policy

Eyes of Rome has two policies with full refund terms.
The policies are included and non-optional.
  1. Dolce Vita policy is applied on all Standard Bookings placed more than 72 hours from the date of the event. We provide all our customers with Refundable Terms up to 72 hours from the date of the event for any reason. To apply for a refund including where your tour is cancelled or changed by Eyes of Rome®, please contact our customer service team at info@eyesofrome.com.
  2. Peace of Mind policy is applied on Selected Bookings and on all Bookings placed within 72 hours from the date of the event. We provide all our customers with Refundable Terms so if you are unable to attend your booking due to unforeseen circumstances outside of your control you may be entitled to a refund - please see our full set of Refundable Terms and Conditions here. To apply for a refund, please find the instructions on how to apply in the booking confirmation email you received after payment.

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