Small-Group Siena and San Gimignano With Dinner in a Boutique Winery

This small-group day trip offers a unique opportunity to take in the captivating history and vibrant culture of Tuscany. Travelers will explore the charming backstreets of Siena, uncover the traditions of its historic contrades, and discover the medieval hilltop town of San Gimignano. The experience culminates with a visit to a boutique Chianti winery, where guests will indulge in a guided wine tasting and a delectable Tuscan dinner. This well-rounded tour promises to provide a deeper appreciation of the region’s rich heritage. What secrets might these enchanting destinations hold?

Key Points

• Explore the charming medieval towns of Siena and San Gimignano, including guided walking tours, on this small-group day trip.
• Discover Siena’s unique contrade traditions and enjoy a surprise local specialty tasting.
• Visit a boutique Chianti winery for a guided wine tasting and 3-course Tuscan dinner.
• Admire the iconic medieval towers of San Gimignano and browse the local shops.
• Travel in a luxury minibus or minivan with an English-speaking driver and tour leader.

Tour Overview

This small-group day trip takes visitors to the historic towns of Siena and San Gimignano, as well as a Chianti winery for a wine tasting and 3-course dinner.

You’ll explore the charming backstreets and main square of Siena, learning about the city’s contrades and traditions.

Then, you’ll have free time to discover the medieval architecture and local shops in the hilltop town of San Gimignano.

The highlight is a visit to a Chianti winery at sunset, where you’ll savor an authentic Tuscan dinner paired with the region’s renowned wines.

Transportation is provided by a luxury Mercedes minibus or minivan, with an English-speaking driver/tour leader to guide you throughout the day.

Siena Walking Tour

The walking tour through Siena’s charming backstreets takes visitors to the historic Piazza del Campo, the city’s main square.

Here, participants learn about Siena’s unique contrade, or neighborhoods, each with its own flag, symbol, and traditions.

The guide shares insights into the city’s medieval history and culture, pointing out architectural highlights like the Palazzo Pubblico and the Mangia Tower.

Visitors also get to enjoy a surprise local specialty tasting, providing a delightful sensory experience.

Throughout the tour, the guide encourages questions, ensuring participants leave with a deeper understanding of Siena’s rich heritage.

The walking tour is an engaging and informative way to discover the heart of this captivating Tuscan city.

Exploring Siena’s Contrades

Siena’s contrades, or neighborhoods, are the heart of the city’s unique cultural identity, each with its own distinct flag, symbol, and time-honored traditions.

Visitors can learn about these fascinating contrades during the guided walking tour of Siena. The guide will explain the intense rivalry between the 17 contrades and how they compete fiercely against each other, especially during the renowned Palio di Siena horse race.

Guests will see the contrade’s ornate fountain and visit the Duomo, where each contrade has its own chapel. This insider look at Siena’s vibrant traditions provides a deeper understanding of the city’s medieval roots and the pride its residents take in their local heritage.

Discovering Local Specialties

Beyond exploring Siena’s contrades, the tour also includes a surprise local specialty tasting, allowing visitors to savor the unique flavors that define the city’s culinary heritage.

During this tasting, you’ll have the chance to indulge in a local delicacy that’s a true reflection of Siena’s gastronomic traditions. Whether it’s a traditional pastry, a regional cheese, or a specialty cured meat, you’ll get to experience the authentic taste of the city.

This unexpected treat is sure to leave a lasting impression, as you discover the rich and diverse flavors that make Siena’s cuisine so acclaimed.

Wandering San Gimignano

Visitors then journey to the medieval hilltop town of San Gimignano, where they can explore its iconic architecture and charming local shops at their own pace.

The town’s medieval towers, a UNESCO World Heritage site, stand tall, offering stunning views of the surrounding Tuscan countryside.

Guests can wander through the town’s narrow streets, popping into artisanal boutiques and sampling local delicacies like the famous gelato.

With free time to discover San Gimignano, travelers can enjoy the town’s rich history and vibrant culture.

Whether browsing the local shops or simply soaking in the peaceful atmosphere, San Gimignano provides a delightful respite from the hustle and bustle of daily life.

Relaxing in the Hilltowns

Relaxing in the hilltowns offers travelers a chance to unwind and soak in the peaceful atmosphere of these historic Tuscan gems. After exploring the lively streets of Siena, visitors can meander through the charming medieval alleyways of San Gimignano, taking in the stunning architecture and soaking up the tranquil ambiance of this UNESCO-protected town.

Activity	Duration	Recommendation
Explore Local Shops	1-2 hours	Browse the artisanal shops and boutiques for unique souvenirs
Climb the Towers	30-60 minutes	Climb the famous towers for panoramic views of the countryside
Enjoy Gelato	30 minutes	Indulge in a refreshing scoop of authentic Italian gelato

With its serene setting and well-preserved medieval features, San Gimignano provides the perfect respite from the busier cities, allowing visitors to truly savor the essence of Tuscany.

Chianti Winery Experience

After exploring the charming hilltowns, travelers head to a Chianti winery to cap off the day with a memorable winery experience.

At the boutique winery, they’ll be greeted by the passionate owner who’ll guide them through a tasting of the estate’s renowned Chianti wines.

As the sun sets over the vineyards, guests will savor a delicious 3-course Tuscan dinner expertly paired with the winery’s finest offerings. It’s the perfect way to take in the rich culinary traditions of the region.

With the knowledgeable staff on hand, travelers come away with a deeper appreciation for Chianti’s winemaking heritage and the care that goes into crafting these exceptional bottles.

Tour Logistics

The tour begins with transportation by a luxury Mercedes minibus or minivan, providing a comfortable journey for guests. An English-speaking driver and tour leader accompany the small group, ensuring a seamless and informative experience throughout the day.

Included	Duration
Transportation	Approximately 10 hours
Guided Tours	–
3-Course Dinner	–
Wine Tasting	–
Small Group	–

The tour is designed to maximize the time spent exploring Siena, San Gimignano, and the Chianti winery, with a perfect balance of guided experiences and free time to immerse in the local culture and charm.

Frequently Asked Questions

Is There a Dress Code for the Winery Dinner?

There’s generally no strict dress code for the winery dinner, but smart casual attire is recommended to blend in with the setting. Comfortable clothing and shoes are advised for the day’s activities.

Can Dietary Restrictions Be Accommodated on This Tour?

Yes, dietary restrictions can typically be accommodated on this tour. Guests should inform the tour provider of any dietary needs when booking, so the winery can prepare an appropriate meal. The tour provider aims to cater to various dietary requirements.

Is There a Maximum Group Size for This Small-Group Tour?

The tour has a maximum group size, typically ranging from 8 to 15 people. The small-group format ensures a more personalized experience and allows for easy transportation and navigation through the historic towns.

Are There Any Additional Fees or Taxes Not Included in the Price?

The price typically covers the guided tours, 3-course dinner with wine, and transportation. However, there may be additional fees or taxes not included, such as entrance fees or optional activities. It’s best to check with the tour provider for full details.

What Is the Cancellation Policy for This Tour?

The cancellation policy allows full refunds for cancellations up to 24 hours before the tour. Cancellations within 24 hours incur a 50% charge. No-shows forfeit the full tour price.

Recap

This small-group day trip offers an immersive exploration of Siena’s charming backstreets, the historic Piazza del Campo, and the unique contrades.

Travelers will also discover the medieval hilltop town of San Gimignano, culminating in a visit to a boutique Chianti winery for a guided wine tasting and a delicious Tuscan dinner, providing a well-rounded appreciation of Tuscany’s cultural and culinary heritage.