Discover the captivating allure of Tuscany’s medieval towns and renowned wine regions on the Siena: San Gimignano, Chianti & Montalcino Small-Group Tour. Embark on an 11-hour journey that immerses you in the region’s rich history, stunning landscapes, and world-famous vintages. From the iconic towers of San Gimignano to the prestigious wineries of Chianti and Montalcino, this tour offers an unparalleled opportunity to experience the essence of Tuscany. With personalized attention and a maximum of 8 participants, you’ll explore the cultural and culinary delights that have made this corner of Italy a coveted destination for travelers worldwide.

Key Points

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - Key Points

  • This small-group tour offers an immersive 11-hour journey through the medieval town of San Gimignano, the Chianti wine region, and the UNESCO-recognized Val d’Orcia.
  • Participants can enjoy wine tastings, including the renowned Brunello from Montalcino, and have the opportunity to purchase wine directly from the wineries.
  • The tour provides a personalized experience with a maximum group size of 8 and a bilingual tour escort to offer expert commentary.
  • Highlights include the iconic medieval towers of San Gimignano, the picturesque Chianti countryside, and the stunning landscapes of the Val d’Orcia region.
  • The tour is not suitable for wheelchair users or participants with significant mobility challenges due to the requirement of stair climbing.
You can check if your dates are available here:

Tour Overview

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - Tour Overview

The tour offers visitors the chance to discover the enchanting medieval town of Siena and its surrounding Tuscan gems.

Named "Siena: San Gimignano, Chianti & Montalcino Small-Group Tour," it’s an 11-hour journey that takes travelers to several iconic destinations.

The tour’s maximum group size is 8 participants, ensuring a personalized experience.

Highlights include exploring the medieval town of San Gimignano, savoring wine tastings in the Chianti region, and visiting the UNESCO World Heritage Site of Val d’Orcia.

Participants can also purchase wine directly from the wineries at special prices.

With a bilingual tour escort and comfortable air-conditioned transportation, this small-group tour provides an immersive Tuscan experience.

Highlights of the Itinerary

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - Highlights of the Itinerary

The tour begins with a visit to the captivating medieval town of San Gimignano, renowned for its iconic skyline of towers.

Guests will have free time to explore the town, home to Italy’s first DOCG wine, Vernaccia, and browse the charming shops.

Next, the group travels to the renowned Chianti wine region, stopping at a prestigious winery for a tasting.

An optional local lunch featuring Tuscan specialties like salami and cheese can be added.

The tour then continues to the UNESCO World Heritage Site of Val d’Orcia and the historic town of Montalcino, known for its famous Brunello DOCG wine, which is sampled at a local cellar.

San Gimignano: Medieval Towers

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - San Gimignano: Medieval Towers

Known for its iconic skyline of medieval towers, San Gimignano is a captivating town that transports visitors back in time.

This UNESCO World Heritage Site boasts 14 remarkably preserved towers, towering up to 54 meters high.

Wandering the charming cobblestone streets, you’ll be struck by the town’s well-preserved medieval architecture and stunning views.

San Gimignano is also famous for its Vernaccia, Italy’s first DOCG wine.

During your visit, explore the quaint shops, sample local delicacies, and soak in the historic atmosphere that has earned San Gimignano its reputation as one of Tuscany’s most picturesque destinations.

Chianti Region: Wine Tasting

One of the highlights of the tour is the opportunity to explore the renowned Chianti wine region. Guests will visit a prestigious winery in the heart of Chianti, where they’ll have the chance to indulge in a delightful wine tasting.

This experience not only allows them to sample the region’s renowned Chianti wines but also provides insights into the centuries-old winemaking traditions that have shaped this iconic Italian wine.

The tour also offers an optional local lunch, where participants can savor a selection of typical Tuscan delicacies like salami and cheese, perfectly complementing the wine tasting.

  • The Chianti region is renowned for its rolling hills, medieval villages, and world-class wines.
  • The wine tasting at the prestigious winery offers a chance to explore the complex flavors and aromas of Chianti wines.
  • Pairing the wine tasting with a traditional Tuscan lunch creates an immersive culinary experience.
More Great Thing To Do Nearby

Val D’orcia: UNESCO Exploration

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - Val Dorcia: UNESCO Exploration

Nestled within the picturesque landscapes of Tuscany, the Val d’Orcia region is a UNESCO World Heritage Site that captivates visitors with its rolling hills, quaint villages, and stunning vistas.

The tour includes an exploration of this breathtaking area, allowing participants to enjoy the rich cultural heritage and natural beauty of the region.

Visitors will have the opportunity to wander through charming towns, admire the iconic cypress-lined roads, and take in the panoramic views that have inspired artists and photographers for centuries.

This UNESCO-protected treasure is a highlight of the Siena Small-Group Tour, offering a truly authentic Tuscan experience.

Montalcino: Brunello Wine Tasting

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - Montalcino: Brunello Wine Tasting

After exploring the stunning landscapes of the Val d’Orcia, the tour continues to the charming town of Montalcino.

The highlight of this stop is a visit to a local cellar for a wine tasting of the renowned Brunello, a DOCG wine produced in the region. Brunello is considered one of Italy’s finest and most prestigious red wines, known for its complexity, depth, and aging potential.

The tasting offers an opportunity to:

  • Explore the nuances and characteristics of this exceptional wine.
  • Appreciate the winemaking traditions and terroir that contribute to Brunello’s excellence.
  • Potentially purchase bottles at special prices to savor the flavors of Montalcino long after the tour.

Transportation and Guide

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - Transportation and Guide

For this small-group tour, you will travel by air-conditioned minivan.

A bilingual tour escort fluent in Spanish, English, and Italian will accompany the group, providing expert commentary and guidance throughout the day.

However, the tour isn’t suitable for wheelchair users, as it requires participants to be able to climb and descend stairs at various locations.

The tour’s accessibility is limited, and those with mobility challenges may find it difficult to fully participate in the sightseeing and activities.

Inclusions and Customer Reviews

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - Inclusions and Customer Reviews

The small-group tour includes visits to the medieval town of San Gimignano, a prestigious winery in the Chianti region, and the city of Montalcino, home to the renowned Brunello DOCG wine.

Participants will have the opportunity to enjoy wine tastings and sample typical Tuscan snacks. The tour also provides an option to purchase wine from the winery at special prices, with shipping available.

According to customer reviews, the tour has an overall rating of 4.7/5 based on 161 reviews, with highlights such as the guide’s knowledge, transportation comfort, and the quality of the wine tastings.

  • Discover the birthplace of Vernaccia, Italy’s first DOCG wine, in San Gimignano.
  • Savor the renowned Brunello di Montalcino during a tasting at a local cellar.
  • Explore the UNESCO World Heritage Site of the Val d’Orcia region.

Frequently Asked Questions

Can I Bring My Own Food and Drinks on the Tour?

No, bringing your own food and drinks is generally not allowed on the tour. The tour includes wine tastings and an optional typical Tuscan lunch, which are part of the overall experience curated by the tour operator.

Do I Need to Bring Any Special Equipment or Clothing?

The tour doesn’t require any special equipment or clothing. Comfortable walking shoes are recommended, as the tour involves some walking. Participants should dress appropriately for the weather and terrain during the tour.

What Is the Minimum Age Requirement for This Tour?

The tour doesn’t specify a minimum age requirement. However, participants should be able to climb and descend stairs, so it’s likely not suitable for very young children. As long as they can handle the physical aspects, there’s no age limit.

Are There Any Vegetarian or Dietary Options Available?

The tour offers vegetarian options and accommodates dietary requirements with advance notice. Guests can enjoy local Tuscan snacks and an optional lunch featuring regional specialties that cater to various dietary needs.

Can I Extend My Stay in Siena Before or After the Tour?

Guests can extend their stay in Siena before or after the tour, though this isn’t included in the package. They’ll need to book additional accommodations separately and ensure they arrive at the meeting point on time.

Recap

The Siena: San Gimignano, Chianti & Montalcino Small-Group Tour offers an immersive exploration of Tuscany’s enchanting landscapes, medieval towns, and renowned wine regions. With personalized attention and comfort, travelers can experience the iconic towers of San Gimignano, indulge in prestigious Chianti wines, and savor the acclaimed Brunello of Montalcino, all while delving into the stunning UNESCO-protected Val d’Orcia. This comprehensive tour provides an unparalleled opportunity to discover the rich cultural and culinary delights of this captivating Italian destination.

You can check if your dates are available here: