Tuscany’s medieval marvels await those seeking a captivating journey beyond Florence. This private tour unlocks the historic gems of Siena, Monteriggioni, and San Gimignano, where iconic architecture and captivating histories come alive. Travelers will marvel at Siena’s grand Duomo, wander Monteriggioni’s walled town, and explore San Gimignano’s towering medieval structures. Along the way, they’ll savor premium Tuscan wines and olive oil, seeing the renowned viticulture of the region. This immersive experience promises to unveil the authentic, UNESCO-listed wonders that make Tuscany’s countryside so alluring. What secrets might these medieval towns hold?

Key Points

From Florence: Private Siena, San Gimignano + Wine Tasting - Key Points

  • Explore the medieval towns of Siena, Monteriggioni, and San Gimignano, known for their iconic architecture and historic significance.
  • Visit the stunning Siena Cathedral, Piazza del Campo, and other architectural gems on a guided tour of the city.
  • Discover the well-preserved medieval walls and charming central piazza of Monteriggioni, a 13th-century town.
  • Taste premium Tuscan wines, including the renowned Vernaccia, and sample high-quality extra virgin olive oil at a local winery.
  • Wander the picturesque streets and towers of San Gimignano, the ‘Manhattan of the Middle Ages,’ and learn about its captivating past.

Discover Authentic Tuscan Gems

From Florence: Private Siena, San Gimignano + Wine Tasting - Discover Authentic Tuscan Gems

This tour takes visitors on a journey through three authentic Tuscan gems – Siena, Monteriggioni, and the UNESCO-listed town of San Gimignano.

In Siena, you’ll explore the historic Piazza del Campo and Piazza del Duomo, with ample free time to visit the stunning Duomo or indulge in local cuisine.

The medieval town of Monteriggioni, built in 1213, offers a glimpse into Tuscany’s past, complemented by a typical Tuscan lunch.

San Gimignano, known for its iconic towers, provides an opportunity to wander its charming streets and admire the breathtaking landscape.

Throughout the tour, you’ll discover the region’s rich cultural heritage and have the chance to savor premium local wines and olive oil.

Explore Medieval Churches and Castles

From Florence: Private Siena, San Gimignano + Wine Tasting - Explore Medieval Churches and Castles

Visitors can explore several medieval churches and castles throughout the tour, including Siena’s Duomo, a stunning example of Romanesque-Gothic architecture.

The tour also includes:

  • Exploring the historic Piazza del Campo in Siena, home to the iconic Palazzo Pubblico and Torre del Mangia
  • Visiting the medieval town of Monteriggioni, with its well-preserved 13th-century walls and gates

Discovering the UNESCO-listed town of San Gimignano, famous for its medieval towers and historic churches.

Admiring the Romanesque-style Collegiate Church in San Gimignano, with its beautiful frescoes.

Learning about the architecture and history of these stunning medieval sites during the guided tours.

Guided Tour of Siena

From Florence: Private Siena, San Gimignano + Wine Tasting - Guided Tour of Siena

The guided tour of Siena begins with a visit to the iconic Piazza del Campo, the city’s central square and the site of the famous Palio horse race.

Here, the guide will share the square’s rich history and architectural wonders, including the impressive Palazzo Pubblico and its iconic Torre del Mangia.

Next, the tour moves on to the stunning Siena Cathedral, a magnificent example of Italian Gothic architecture.

Visitors will have the opportunity to admire the cathedral’s intricate façade, ornate interior, and the magnificent pulpit designed by Nicola Pisano.

Throughout the tour, the guide will provide insights into Siena’s medieval past, its traditions, and the significance of the city’s well-preserved historic center, a UNESCO World Heritage site.

Free Time in Siena

From Florence: Private Siena, San Gimignano + Wine Tasting - Free Time in Siena

After the guided tour, travelers can spend the remaining time in Siena as they please. They’re free to visit the Duomo, browse the local shops, or savor the city’s renowned cuisine at their own pace.

Some recommended activities include:

  • Touring the iconic Siena Cathedral, a stunning example of Italian Gothic architecture

  • Strolling through the charming streets and squares, popping into local boutiques and artisan workshops

  • Indulging in a leisurely lunch or aperitif at one of the inviting cafes or trattorias in Piazza del Campo

  • Climbing to the top of the Mangia Tower for panoramic views over the city and the surrounding Tuscan landscape

  • Exploring the historic Palazzo Pubblico, home to the Civic Museum and its impressive art collection.

Visit Monteriggioni

From Florence: Private Siena, San Gimignano + Wine Tasting - Visit Monteriggioni

From Siena, the tour proceeds onwards to the medieval town of Monteriggioni, built all the way back in 1213. Travelers can expect to enjoy a typical Tuscan lunch during their visit to this well-preserved hilltop fortress.

The highlights of Monteriggioni include:

Highlight Description
Walls The intact medieval walls, nearly a mile in circumference, provide a glimpse into the town’s storied past.
Towers The 14 towers adorning the walls were once used for defense and surveillance.
Piazza The central piazza offers a peaceful setting to soak in the town’s charming atmosphere.
Churches Several historic churches, such as the Church of St. Mary, can be explored.
Views Sweeping views of the Sienese countryside can be admired from the town’s elevated position.

Typical Tuscan Lunch

From Florence: Private Siena, San Gimignano + Wine Tasting - Typical Tuscan Lunch

During their visit to Monteriggioni, travelers can expect to savor a traditional Tuscan lunch, seeing the town’s rich culinary heritage.

The meal typically features:

  • Local cheeses and cured meats
  • Fresh, seasonal vegetables
  • Handmade pasta dishes
  • Hearty meat-based entrees
  • Renowned Chianti or Vernaccia wines

This authentic dining experience allows visitors to truly appreciate the flavors and traditions that have defined Tuscan cuisine for centuries. The unhurried meal provides a chance to savor each bite, engage with the local culture, and leave with a deeper understanding of the region’s gastronomic identity.

Explore San Gimignano

From Florence: Private Siena, San Gimignano + Wine Tasting - Explore San Gimignano

Travelers often explore the UNESCO-listed town of San Gimignano, renowned for its iconic skyline of medieval towers that have earned it the nickname ‘the Manhattan of the Middle Ages’.

This charming town boasts over a dozen surviving towers, some reaching heights of 50 meters. Visitors can wander through the town’s cobblestone streets, admiring the Gothic architecture and stopping to sample local delicacies like the famous Vernaccia white wine.

With free time to discover San Gimignano’s hidden gems, travelers can visit quaint shops, historic churches, and panoramic viewpoints offering stunning vistas of the surrounding Tuscan countryside.

Exploring this well-preserved medieval gem is a highlight of the tour, providing a glimpse into Tuscany’s captivating past.

Premium Wine Tasting

From Florence: Private Siena, San Gimignano + Wine Tasting - Premium Wine Tasting

After exploring the medieval charm of San Gimignano, the tour moves on to a local winery where visitors can enjoy the art of Tuscan winemaking.

Here, they’ll learn about the region’s renowned viticulture and have the opportunity to sample some of its finest offerings.

  • Guided tour of the winery, offering insights into the winemaking process
  • Tasting of premium Tuscan wines, including the famous Vernaccia white wine
  • Sampling of high-quality extra virgin olive oil, another local specialty
  • Chance to purchase wines and olive oil to take home as souvenirs
  • Expert sommelier on hand to provide tasting notes and answer questions

This wine tasting experience provides a perfect complement to the day’s exploration of Tuscany’s historic towns and landscapes.

Frequently Asked Questions

From Florence: Private Siena, San Gimignano + Wine Tasting - Frequently Asked Questions

What Is the Minimum Group Size for This Tour?

The minimum group size for this tour is not specified. This tour is a private experience, so the group size is flexible and can accommodate solo travelers or larger parties as needed.

Is Hotel Pickup and Drop-Off Included in the Tour?

The tour does not include hotel pickup or drop-off. Participants are responsible for making their own way to the tour’s starting point and getting back to their accommodations after the tour concludes.

Can Dietary Requirements Be Accommodated During the Lunch?

Yes, dietary requirements can typically be accommodated during the lunch. The tour provider is usually able to cater to various dietary needs, such as vegetarian, vegan, or gluten-free options, with advance notice.

Are There Any Discounts Available for Children or Seniors?

Yes, there are typically discounts available for children and seniors on tours. Customers should inquire about any special pricing or reduced rates when booking. Exact discounts may vary depending on the tour provider and destination.

How Much Time Is Spent at Each Location During the Tour?

The tour typically spends 2-3 hours in Siena, 1 hour in Monteriggioni, 2 hours in San Gimignano, and 1 hour for the wine tasting, allowing visitors ample time to explore each destination.


This private tour offers a deep dive into Tuscany’s historic wonders.

Visitors will marvel at the medieval architecture of Siena, Monteriggioni, and San Gimignano, and savor premium Tuscan wines and olive oil.

The immersive experience provides a chance to explore the authentic, UNESCO-listed countryside and gain insights into the region’s renowned viticulture.

It’s an ideal way to discover the historic gems of this captivating destination.

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