Experience the quintessential heart of Tuscany on this exclusive small-group full-day tour from Siena, leading you through the iconic, rolling landscapes of the Val d’Orcia and into the historic charm of the hill towns of Pienza and Montepulciano. This carefully curated journey is designed for those who seek an intimate, authentic taste of the region’s culture, history, and, most importantly, its globally celebrated wines and gourmet food. Limited to a maximum of eight participants, this tour ensures a personalized and enriching experience, far removed from the crowds of larger excursions.

Your day begins with a scenic drive south from Siena, tracing one of Tuscany’s most breathtaking routes through the characteristic, almost lunar landscape of the Crete Senesi. This area, famous for its clay hills, offers incredible photo opportunities and sets a serene tone for the adventures ahead. The journey immerses you in the natural beauty that has defined Tuscany for centuries, leading you into the UNESCO World Heritage-listed Val d’Orcia, a region whose cypress-lined hills and solitary farmhouses perfectly capture the postcard-perfect image of the Italian countryside.

The first major stop is the utopian Renaissance town of Pienza. Commissioned by Pope Pius II to be his “ideal city,” Pienza is a masterpiece of Renaissance urban planning. Here, you’ll have leisure time to wander its perfectly proportioned streets, admire the architectural splendor of the Piazza Pio II with its Cathedral and Piccolomini Palace, and take in the spectacular views from the town walls overlooking the Val d’Orcia valley. Pienza is also renowned for its Pecorino cheese, and its charming shops offer a delightful opportunity to browse and sample this local delicacy.

Midday brings a genuine culinary highlight: a wholesome, traditional lunch at a local, sustainable farm in the Val d’Orcia. This farm-to-table experience allows you to savor dishes made with fresh, local ingredients, often served on a terrace with sweeping views of the picturesque valley. Paired with local wine, this relaxing and convivial meal provides a deep connection to the regional gastronomy.

The afternoon is dedicated to the magnificent hilltop town of Montepulciano, a proud and imposing city with a rich history, having been influenced by both Siena and Renaissance Florence. Montepulciano is synonymous with one of Italy’s oldest and most prestigious wines, Vino Nobile di Montepulciano DOCG. After a guided stroll through the town’s historic center, including the grand Piazza Grande surrounded by noble palaces, the true exploration of the town’s viticultural heritage begins. You will have the opportunity to delve into one of the ancient, subterranean wine cellars carved deep into the tufa rock beneath the city. These historic cantine offer a cool, atmospheric environment perfect for aging the noble wine. The experience culminates in a cellar tour and a well-deserved tasting of the esteemed Vino Nobile, providing an in-depth appreciation for the region’s winemaking tradition. You’ll have time afterward for independent exploration, perhaps discovering a local artisan shop or simply soaking in the spectacular views from this lofty perch.

Highlights of Pienza and Montepulciano Small-Group Tour

• Discover the quaint medieval hamlet of Pienza
• Sample the noble wines of Montepulciano
• Wander among the noble palaces of Montepulciano
• Enjoy lunch on the terrace of a local farm with wine

• Round trip transportation by air-conditioned minivan
• 3 course meal and pecorino cheese tasting at an organic farm
• Cellar tour and wine tasting in Montepulciano

• Hotel pick-up
• Museum tickets

.Meet your guide under the large tree that is in front of the Basilica in Piazza San Domenico, Siena

What to bring

• Comfortable shoes

Know before you go

• Comfortable walking shoes are recommended