Grand Tour of Pienza, Montalcino, Montepulciano + Wine and Cheese Tasting

Set out on a captivating journey through the heart of Tuscany’s historic towns, where Renaissance architecture and world-renowned wines converge. Explore the UNESCO-listed gem of Pienza, stroll the charming streets of Montepulciano, and indulge in a guided tour through a celebrated Montalcino winery, sipping the region’s acclaimed Brunello. Along the way, savor local artisanal cheeses and delectable snacks, all while enjoying the comfort of private transportation and personalized attention in an intimate group setting. This immersive Tuscan experience promises to captivate your senses and leave you eager to uncover more.

This experience made our list of the 11 Best Wine Tours In Chianti.

Quick Points

• Explore the UNESCO-listed Pienza, the "ideal city" designed by Bernardo Rossellino, with visits to the Palazzo Piccolomini, Duomo, and Piazza Pio II.
• Discover the historic Renaissance palaces of Montepulciano, including the Palazzo Comunale, Palazzo del Capitano, and Palazzo Tarugi, showcasing the city’s architectural prosperity.
• Enjoy a guided winery tour and Brunello tasting in Montalcino, known for its acclaimed red wine, and learn about the winemaking process and terroir.
• Savor local cheeses, Ricotta, Pecorino, and artisanal salami, paired with Brunello or Rosso di Montalcino, providing a culinary highlight after the winery tour.
• Experience a private, small-group tour with personalized attention and flexibility, ensuring a seamless and immersive journey through Tuscany’s culture, architecture, and gastronomy.

Exploring the Renaissance Palaces of Montepulciano

On this tour, visitors will explore the magnificent Renaissance palaces that dot the historic city center of Montepulciano.

The tour guide will lead the group through the picturesque streets, stopping to admire the impressive architecture of the Palazzo Comunale, Palazzo del Capitano, and Palazzo Tarugi.

Guests will learn about the history and significance of these grand buildings, which showcase the city’s prosperity during the Renaissance era.

From ornate facades to intricate interiors, each palace offers a glimpse into Montepulciano’s cultural heritage.

Visitors will also have the opportunity to wander through the charming piazzas and medieval alleyways that surround these architectural gems.

Discovering the UNESCO World Heritage Site of Pienza

The tour now moves to the UNESCO World Heritage Site of Pienza.

This charming Renaissance town was designed by the architect Bernardo Rossellino in the 15th century. Visitors will wander through the picturesque streets, admiring the elegant Palazzo Piccolomini, the magnificent Duomo, and the central Piazza Pio II.

The guide will share the history of this unique town, which was commissioned by Pope Pius II as an "ideal city." Guests can marvel at the well-preserved architecture and soak in the serene atmosphere.

Pienza’s designation as a UNESCO site reflects its cultural and historical significance, making it a highlight of the tour.

Guided Winery Tour and Brunello Tasting in Montalcino

The tour now takes guests to Montalcino, known for its acclaimed Brunello wine. A guided winery tour provides an in-depth look at the wine’s production process.

Visitors learn about the region’s unique terroir and aging requirements that contribute to Brunello’s distinctive flavor profile. The highlight is a tasting of these prestigious red wines, allowing guests to savor the complex notes of cherry, spice, and oak.

This immersive experience not only educates but also delights the palate, offering a deeper appreciation for the art of winemaking in Montalcino.

The tour continues to explore the charming medieval town, providing a well-rounded introduction to the renowned wine region.

Savoring Local Cheese and Snacks

Following the tour of the Brunello winery, guests have the chance to savor a selection of local cheeses and other delectable snacks.

This is a welcome respite after the walking tour, allowing visitors to indulge in the flavors that make this region renowned.

The cheese tasting features:

• Pecorino, a classic sheep’s milk cheese from nearby Pienza
• Ricotta, a creamy and fresh cheese often used in local dishes
• Artisanal salami, cured to perfection and paired beautifully with the wines

Along with these delightful bites, guests can enjoy a glass of Brunello or Rosso di Montalcino, continuing their exploration of the region’s renowned vintages.

Private Transportation and Small Group Experience

Guests are whisked away in private transportation to the tour’s destinations, ensuring a seamless and comfortable experience. The tour is conducted in a small group setting, allowing for a more personalized and interactive exploration of the historic towns. This intimate group size also enables the guide to provide a more tailored experience, catering to the unique interests and questions of each participant.

Group Size	Advantages
Small	• More personalized attention • Ability to ask questions • Flexibility to adjust pace
Large	• Lower cost per person • Potentially less individual engagement • Less flexibility

The private transportation and small group format create an immersive and memorable journey through the enchanting Tuscan countryside.

Confirmation and Cancellation Details

Confirmation of the tour is provided within 48 hours of booking, ensuring guests have all the necessary details before their experience.

The tour offers flexibility with a free cancellation policy up to 24 hours before the start of the experience. Additionally:

• The tour is private, catering to your group only, for a personalized experience.
• It’s wheelchair and stroller accessible, making it suitable for a wide range of travelers.
• Service animals are allowed, accommodating all guests.

Operated by the experienced guide Roberta Marioni, this tour provides a seamless and enjoyable journey through the enchanting towns of Pienza, Montalcino, and Montepulciano.

Glowing Reviews From Previous Guests

Travelers rave about the exceptional experience offered by this private tour, with a perfect 5-star rating based on a recent review.

One guest enthusiastically stated, "This tour was the highlight of our trip to Italy! Our guide was incredibly knowledgeable and passionate, bringing the history and culture of each town to life."

Guests appreciate the intimate nature of the private tour, which allows for a more personalized and immersive experience.

With access to exclusive winery tastings and charming Renaissance sites, this tour provides an unforgettable glimpse into the heart of Tuscany’s picturesque countryside and legendary wine region.

Since You Asked

What Is the Maximum Group Size for This Tour?

The tour can accommodate up to 10 people in the group. The pricing is listed as "From $375.97 per group (up to 10)", indicating that the maximum group size for this private tour is 10 people.

Is the Tour Accessible for People With Disabilities?

The tour is wheelchair and stroller accessible, and service animals are allowed, making it accessible for people with disabilities. The provider ensures a comfortable experience for all guests.

Are Children Allowed on the Tour?

Yes, children are allowed on the tour. The tour is wheelchair and stroller accessible, indicating that families with young children can participate. Travelers should confirm any age restrictions or special accommodations with the local provider before booking.

Can the Tour Be Customized to Individual Preferences?

Yes, the tour can be customized to individual preferences. The provider is flexible and willing to accommodate requests, such as adding or removing activities, to ensure the tour meets the needs of each group.

How Long Does the Entire Tour Last?

The entire tour lasts approximately 7-8 hours. The itinerary includes stops in Pienza, Montalcino, and Montepulciano, with guided visits, wine tastings, and cheese samplings. The starting and ending point is in Montalcino.

The Final Verdict

Set out on a captivating Grand Tour through the enchanting Tuscan towns of Pienza, Montalcino, and Montepulciano. Explore Renaissance architecture, indulge in a guided winery tour, and savor local cheeses paired with regional wines. With private transportation and personalized attention in a small group setting, this unforgettable Tuscan experience is not to be missed.