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

Discover the essence of Tuscany on this immersive small-group tour. Explore the medieval gem of Siena, delving into its iconic Piazza del Campo and captivating contrade districts. Indulge in a specialty tasting, savoring the flavors that have defined this region for centuries. Then, journey to the picturesque town of San Gimignano, marveling at its renowned towers and breathtaking vistas. But the day’s true highlight awaits as you venture to a boutique winery, where a Tuscan-style dinner and wine tasting promise to elevate your senses and leave you with memories that’ll linger long after the sun sets over the rolling Chianti hills.

This experience made our list of the 25 Best Dinner Tours In Florence.

Key Points

• Explore the historic cities of Siena and San Gimignano, including iconic landmarks like Piazza del Campo and medieval towers.
• Discover the unique districts, traditions, and rivalries of Siena’s contrade during a guided tour.
• Indulge in a quintessential Sienese specialty tasting, immersing in the city’s rich gastronomic heritage.
• Enjoy a 3-course Tuscan dinner with wine tasting at a boutique winery in the Chianti countryside.
• Savor the breathtaking sunset over the rolling Tuscan hills from the winery’s terrace during the dinner.

Tuscan Countryside Exploration

On this immersive tour, guests will venture into the picturesque Tuscan countryside, where rolling hills, endless vineyards, and historic towns await their discovery.

The journey begins with a drive through the scenic Chianti region, known for its world-renowned wines and charming villages. Along the way, travelers will catch glimpses of the region’s iconic cypress trees, medieval castles, and olive groves.

This countryside exploration sets the tone for the day, allowing guests to fully enjoy the quintessential Tuscan experience. With the guidance of an English-speaking driver, visitors will have the opportunity to soak up the natural beauty and rich cultural heritage that makes this part of Italy so captivating.

Guided Tour of Siena

After traversing the Tuscan countryside, guests arrive in the historic city of Siena, one of Tuscany’s crown jewels.

During the guided walking tour, they’ll explore the renowned Piazza del Campo, the site of the famous Palio horse races, and explore the intricate contrade (districts) that give the city its distinct character.

A surprise local specialty tasting adds a delightful touch to their Sienese experience.

They’ll learn about Siena’s rich history and admire the stunning medieval architecture that has earned it a reputation as one of Tuscany’s most picturesque destinations.

The guided tour provides an immersive introduction to this captivating city, leaving guests with a deeper appreciation for its enduring allure.

Piazza Del Campo and Contrades

At the heart of Siena’s historic center lies the iconic Piazza del Campo, a UNESCO World Heritage site and the stage for the renowned Palio horse races. This breathtaking square, with its distinctive shell-like shape and elegant architecture, serves as the lively center of the city’s social and cultural life.

Radiating from the piazza are the contrades, the traditional districts that have long played a crucial role in Sienese identity and community. Each contrade has its own unique flag, symbols, and traditions, fostering a deep sense of pride and rivalry among the locals.

During the Palio, these age-old rivalries come to a head as the contrades compete fiercely for the coveted prize, creating an electrifying atmosphere that draws visitors from around the world.

Specialty Tasting in Siena

As part of the immersive Siena experience, the tour includes a surprise local specialty tasting, allowing visitors to indulge in a quintessential Sienese delicacy.

This culinary delight, a closely guarded secret until revealed, provides a genuine glimpse into the city’s rich gastronomic heritage and the pride its people take in their traditional foods.

The guide expertly unveils the hidden gem, sharing its history and the unique techniques used in its preparation. Savoring this unexpected treat, travelers are transported to the heart of Siena, broadening their understanding of the city’s vibrant food culture.

This exclusive tasting moment leaves a lasting impression, highlighting the joy of discovering local specialties and the passion that goes into preserving them.

Picturesque San Gimignano

San Gimignano’s impressive towers rise proudly into the Tuscan sky, captivating visitors with their medieval grandeur.

Wandering through the town’s winding streets, travelers are transported back in time, marveling at the well-preserved architecture and charming shops.

From the top of the towers, sweeping vistas of the rolling countryside unfold, offering a glimpse into the region’s breathtaking natural beauty.

During the free time allotted, guests can explore the town at their own pace, ducking into artisan boutiques, sampling local delicacies, and admiring the town’s iconic silhouette against the backdrop of the Tuscan landscape.

San Gimignano’s timeless appeal makes it a must-visit destination on any Tuscan adventure.

Boutique Winery Dinner

Capping off the day’s Tuscan adventures, guests indulge in a 3-course Tuscan dinner with wine tasting at a boutique Chianti winery, soaking up the serene sunset over the rolling hills.

Guests savor regional specialties in an intimate, outdoor setting, weather permitting. The experience showcases the culinary delights and winemaking traditions of the Chianti region:

• An appetizer course featuring a selection of Tuscan antipasti
• A main course highlighting local, seasonal ingredients
• A decadent dessert paired with the winery’s signature Chianti vintage
• An educational wine tasting led by a knowledgeable sommelier

Scenic vistas of the Chianti countryside from the winery’s terrace.

Sunset, Tuscan-Style

With the sun dipping below the rolling Tuscan hills, guests gather on the winery’s terrace to savor the last warm rays of the day.

The outdoor seating, weather permitting, provides the perfect setting to enjoy a 3-course Tuscan dinner paired with the winery’s finest selection of Chianti wines.

As the sky transforms into a breathtaking canvas of oranges and pinks, the group sips on robust reds, savoring the complex flavors that capture the essence of the region.

It’s a truly magical experience, where the beauty of the Tuscan countryside meets the joy of sharing a meal and making memories with fellow travelers.

This sunset-lit dinner is the perfect crescendo to a day of exploring Siena and San Gimignano.

Tour Logistics and Information

The tour commences with transportation by a luxury Mercedes Minibus or Minivan, ensuring a comfortable and efficient journey through the picturesque Tuscan countryside.

An English-speaking driver/tour leader accompanies the small group, providing expert guidance and insights throughout the day.

This small-group experience offers a more intimate and personalized adventure, allowing for greater flexibility and attention to individual needs.

Gratuities aren’t included, so guests are free to reward exceptional service at their discretion.

Unlike some tours, there’s no hotel pickup or drop-off, allowing for a streamlined and focused exploration of the day’s destinations.

Frequently Asked Questions

Is There an Option for Hotel Pickup and Drop-Off?

The tour does not include hotel pickup or drop-off. Guests are responsible for making their own way to the designated meeting point and returning there after the tour. Transportation is provided by luxury minibus or minivan during the tour.

Can I Bring My Own Wine to the Winery Dinner?

No, guests are not allowed to bring their own wine to the winery dinner. The tour includes a 3-course Tuscan dinner with wine tasting, so bringing outside wine would not be permitted. The winery’s selection is part of the dining experience.

How Many People Are Typically in a Small Group?

Typically, small group tours have between 8 to 15 participants, providing a more intimate and personalized experience than larger group tours. The exact group size may vary depending on the tour operator and the specific itinerary.

Can I Join the Tour if I Have Dietary Restrictions?

Travelers with dietary restrictions can likely join the tour, as the winery dinner typically offers accommodations for various needs. It’s best to inform the tour company of any dietary requirements when booking to ensure a comfortable experience.

Is There a Discount for Booking the Tour in Advance?

Yes, there may be discounts for booking the tour in advance. Many tour operators offer early booking incentives or package deals to encourage customers to reserve their spots ahead of time. Checking the tour provider’s website or contacting them directly can help determine if any discounts are available.

Recap

Explore the charming Tuscan countryside on this small-group tour.

Discover the historic sights of Siena and San Gimignano, indulge in a specialty tasting, and savor a 3-course Tuscan dinner with wine at a boutique winery as the sun sets over the rolling hills.

This immersive experience offers a quintessential taste of the region’s rich culture, architecture, and gastronomy.