Pienza & Montepulciano Tour with Wine Tasting and Farm Lunch

Overview

Wine, culture and stunning scenery await on this exclusive tour of Pienza and Montepulciano in Tuscany’s enchanting Val d’Orcia. Your adventure begins in the rolling hills of Montepulciano, where you’ll visit a top Nobile di Montepulciano producer and taste its legendary wines amidst sun-drenched vineyards. Savor a farm-to-table lunch at an organic cheese farm, and conclude your day exploring Pienza, a stunning Renaissance town renowned for its elegant architecture, charming streets and breathtaking views. With private transport throughout, this is the best way to visit the Val d'Orcia!

Description

Explore Postcard-Perfect Montepulciano

 

Our expert driver-guide will pick you up at your accommodation, and you’ll soon be travelling through the unforgettable landscapes of the Tuscan countryside on the way to Montepulciano, a medieval hilltop town celebrated for its Nobile di Montepulciano - one of Italy’s oldest and most esteemed wines. 

Stroll through the cobblestone streets, where history comes alive in landmarks like Piazza Grande, framed by Renaissance palaces and the Cathedral of the Assumption. Just outside the town, the Temple of San Biagio rises in serene splendor,  an architectural marvel nestled amid lush fields that’s a perfect example of Tuscan Renaissance architecture.  

 

Taste Nobile di Montepulciano at a Renowned Winery

 

As superb as the architecture is, in Montepulciano wine is the main story. We’ll have the opportunity to visit one of the region’s most renowned wineries to learn about the meticulous, centuries-old tradition of viticulture that has made the vintages produced here some of the most sought after in Italy. 

On our tour, we’ll discover every step of the process, from harvesting the Prugnolo Gentile grapes to the carefully controlled ageing process that creates this robust and elegant wine. In the company of master winemakers you’ll get to taste different vintages of Nobile di Montepulciano; guided by their expertise, you’ll learn the characteristic notes and flavor profile that makes this variety unique. 

 

Enjoy a Tuscan Lunch at an Organic Cheese Farm

 

After our wine tasting you’ll be sure to have worked up an appetite, so next stop is lunch at an organic cheese farm! In the heart of Val d’Orcia, you’ll visit a working organic dairy where local sheep graze on herb‑scented hillsides. A guided tour will introduce you to each stage of pecorino production - from milking and curd formation to careful pressing and maturation in stone‑lined cellars. 

On the tour you’ll learn how seasonal pastures and traditional methods combine to create Val d’Orcia’s distinctive pecorino, marrying simplicity with regional character.

Afterwards, you’ll settle in for a relaxed meal that will include the farm’s own cheeses - fresh, aged, and everything in between - paired with wines carefully selected to complement their texture and flavor. 

 

Discover a Hidden Renaissance Gem in Pienza

 

In the afternoon, the tour continues to Pienza, a UNESCO World Heritage Site and an ideal Renaissance city created according to the  vision of Pope Pius II. Its harmonious design unfolds most clearly in Piazza Pio II, home to the majestic Duomo and Palazzo Piccolomini. Framed by honey-colored travertine buildings, this elegant square is a true masterpiece of Renaissance urban planning, and embodies the refined vision of Pope Pius II. 

Adjacent to Piazza Pio II stands the Duomo di Santa Maria Assunta, a symbol of Pienza’s Renaissance glory and a near replica of Florence’s Palazzo della Signoria. Its travertine facade, divided into two sections by a simple cornice, reflects an understated elegance. Inside, the cathedral is divided into three equally tall naves, creating a sense of harmony. Highlights include Vecchietta’s Assumption of the Virgin and Matteo di Giovanni’s Madonna and Child with Saints, masterpieces that bring the space to life. The blend of spiritual and artistic elements makes this a must-visit destination.

Before heading back home in the company of your private driver-guide you’ll have some time to wander through Pienza’s quaint alleys and browse at artisan shops offering the town’s famous pecorino cheese - "il Cacio" - alongside other local specialties like wines from the Crete Senesi, honey, pici pasta, and more.