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

Siena, San Gimignano, Chianti, and Montalcino – these Tuscan gems await adventurous travelers on a small-group tour that promises an immersive experience. Exploring medieval streets, sampling renowned wines, and discovering UNESCO-listed landscapes, this11-hour journey uncovers the region’s captivating history and natural beauty. With a maximum of 8 participants, the tour offers a personalized exploration, ensuring an unforgettable glimpse into the heart of Tuscany. What secrets will this enchanting excursion unveil?

Key Points

• A small-group tour exploring the medieval towns of Siena, San Gimignano, Chianti, and Montalcino, with wine tastings and optional local lunch.
• Discover the iconic skyline of fine towers in San Gimignano, a UNESCO-listed historic market town.
• Immerse in the Chianti wine region, with a visit to a prestigious winery and sampling of regional specialties.
• Tour the picturesque Val d’Orcia, a UNESCO World Heritage Site renowned for its exceptional wines and stunning landscapes.
• Convenient pickup and drop-off within 10 km of Siena, available in multiple languages.

You can check availability for your dates here:

Tour Overview

This small-group tour takes visitors on an 11-hour journey through the captivating landscapes and historic towns of Siena, San Gimignano, Chianti, and Montalcino.

The maximum group size is 8 people, ensuring a personalized experience.

Travelers will explore the medieval streets of San Gimignano, the wine regions of Chianti and Montalcino, and the UNESCO-listed Val d’Orcia.

Along the way, they’ll enjoy wine tastings, an optional local lunch, and free time for sightseeing and shopping.

The tour is available in Spanish, English, and Italian, with pickup and drop-off options for accommodations within 10 km of Siena.

Itinerary Highlights

The tour begins in the medieval town of San Gimignano, known as the "City of Fine Towers."

Visitors will have free time to explore the charming streets, browse local shops, and soak in the town’s historic atmosphere.

Next, the group visits a prestigious Chianti winery for a tasting. An optional lunch featuring local specialties like salami and cheese is available.

In Montalcino, famous for its Brunello wine, the group tours a cellar and samples the renowned vintages.

The tour also includes a stop in the UNESCO World Heritage Site of Val d’Orcia, known for its stunning landscapes.

San Gimignano: The City of Fine Towers

Although small in size, the medieval town of San Gimignano captivates visitors with its iconic skyline of fine towers. Once a thriving market town, San Gimignano’s wealthy families constructed over 70 stone towers as symbols of their power and prosperity.

Today, 14 of these medieval towers remain, creating a unique and picturesque landscape. Visitors can explore the town’s winding streets, admire the impressive architecture, and visit the Collegiata, a Romanesque cathedral known for its stunning frescoes.

San Gimignano’s Vernaccia wine, the first Italian DOCG white wine, is also a highlight for many travelers.

Chianti Region: Wine Tasting and Local Cuisine

After exploring the medieval charms of San Gimignano, the tour journey continues into the renowned Chianti region.

Guests will visit a prestigious Chianti winery for a tasting of the region’s renowned red wines.

There’s also an optional opportunity to enjoy a local lunch featuring salami, cheese, and other regional specialties.

The Chianti countryside offers breathtaking scenery of vineyards and rolling hills, providing a picturesque backdrop for this oenological experience.

Guests will have the chance to savor the flavors that have made Chianti a global wine destination, while seeing the heart of this storied Italian wine region.

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Montalcino: Exploring the Land of Brunello

From Chianti, the tour journeys onward to the town of Montalcino, renowned for its production of the prestigious Brunello di Montalcino wine.

Visitors explore this picturesque town, learning about its winemaking legacy:

Exploring the picturesque town of Montalcino, known for its prestigious Brunello di Montalcino wine and rich winemaking legacy.

• Tour a local wine cellar and sample the rich, full-bodied Brunello, a 100% Sangiovese varietal aged for a minimum of 4 years.

• Take in the scenic views of the 1,500 hectares of vineyards that blanket the surrounding hills.

• Discover the historic Rocca di Montalcino, a 14th-century fortress overlooking the town.

• Stroll the charming streets, admiring the medieval architecture and artisan shops.

• Gain insights into the region’s UNESCO-listed Val d’Orcia landscape.

Val D’orcia: a UNESCO World Heritage Site

The tour’s journey continues into the breathtaking Val d’Orcia, a UNESCO World Heritage Site renowned for its picturesque landscapes.

Guests will explore this rolling countryside, admiring the iconic cypress trees, medieval hilltop towns, and vineyards that stretch as far as the eye can see.

This region is renowned for its exceptional wines, including the prestigious Brunello di Montalcino.

Visitors will have the opportunity to soak in the stunning vistas, seeing the tranquil atmosphere that has inspired artists and writers for centuries.

This UNESCO-protected landscape is a highlight of the tour’s exploration of Tuscany’s natural beauty.

Transportation and Logistics

Customers travel by air-conditioned minivan during the Siena Small-Group Tour.

The meeting point is in front of Hotel Minerva, Via Giuseppe Garibaldi 72, Siena. Pickup and drop-off are excluded, but available for accommodations within 10 km of Siena for an additional fee.

The tour features:

• Travel by comfortable, air-conditioned minivan

• Meeting point at Hotel Minerva in Siena

• Pickup and drop-off available within 10 km of Siena for an extra charge

• Convenient transportation to explore the medieval towns and wine regions

• Easy access to the tour’s key destinations, including San Gimignano, Chianti, and Montalcino.

Customer Feedback and Experience

The Siena Small-Group Tour receives positive feedback from customers. Based on 189 reviews, the tour has an impressive 4.6/5 average rating.

Customers praise the knowledgeable and engaging guides, who bring the history and culture of the destinations to life through their storytelling. The tour’s structure, including the winery visits, also earns praise.

While some suggest more time in certain locations like Pienza, the overall experience seems to meet or exceed customer expectations. The tour’s logistics, including transportation and booking options, contribute to its positive customer reviews.

The Sum Up

The Siena: San Gimignano, Chianti & Montalcino Small-Group Tour offers an immersive experience through Tuscany’s breathtaking landscapes and rich history. Travelers explore medieval towns, savor prestigious wines, and discover UNESCO-listed treasures, all while enjoying a personalized journey with a small group. This tour provides an excellent way to explore the essence of Tuscany, leaving visitors with cherished memories of its stunning beauty and cultural riches.

You can check availability for your dates here: