What if you could step back in time and explore the medieval treasures of Tuscany? Imagine wandering through narrow cobblestone streets, surrounded by centuries-old architecture and breathtaking views.
The enchanting cities of Siena, San Gimignano, and Monteriggioni offer just that, transporting you to a bygone era of knights and noble families. From the imposing city walls of Monteriggioni to the awe-inspiring Duomo of Siena, and the iconic medieval towers of San Gimignano, each destination holds its own unique charm and history.
But that’s not all – a delightful wine tasting in the Chianti region adds a touch of indulgence to this unforgettable journey.
So, why not join this captivating tour and uncover the medieval gems that await you in Tuscany?
Good To Know

- Lowest Price Guarantee, ensuring competitive pricing and affordable options for travelers.
- Flexibility in selecting preferred date and number of travelers.
- Full-day tour of central Tuscany, visiting medieval gems such as Monteriggioni, Siena, and San Gimignano.
- Guided tours of Siena and San Gimignano, with free time to explore Monteriggioni.
Tour Highlights

The tour highlights of the Medieval Gems of Tuscany include exploring picturesque Monteriggioni, immersing in the rich history of Siena, marveling at the stunning skyline of San Gimignano, and indulging in a delightful wine tasting in the Chianti region.
This tour itinerary is carefully crafted to provide travelers with an unforgettable experience, showcasing the historical significance of these enchanting towns.
The journey begins with a drive through the Tuscan countryside, offering breathtaking views as you make your way to Monteriggioni. Here, you’ll have free time to explore this medieval gem on your own, marveling at its well-preserved walls and charming atmosphere.
Next, you’ll embark on a guided tour of Siena, starting at the iconic Piazza del Campo and ending at the magnificent Duomo.
Finally, you’ll visit San Gimignano, known for its striking skyline and medieval towers. After soaking in the beauty of this hilltop town, you’ll have the opportunity to indulge in a wine tasting at a local winery in the Chianti region, savoring the flavors of this renowned wine-producing area.
This tour promises to be a captivating journey through history, culture, and the scenic landscapes of Tuscany.
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Meeting and Pickup Details
Upon arrival at the meeting point in Piazzale Montelungo, Florence, travelers will easily spot the staff wearing distinctive FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD.
Piazzale Montelungo is conveniently located just a 5-10 minutes walking distance from Santa Maria Novella Train Station, making it easily accessible for travelers. This ensures smooth logistics for those arriving by train.
The meeting point is the starting point for the full-day tour of central Tuscany, where medieval gems such as Monteriggioni, Siena, and San Gimignano are waiting to be explored.
The tour begins at 08:45 AM and ends back at the meeting point. Travelers can expect a guided tour of Siena’s old town, starting at the iconic Piazza del Campo and ending at the beautiful Duomo.
Afterward, there will be free time to sightsee and shop in San Gimignano’s historic center before indulging in a wine tasting at a local winery in the Chianti region.
Explore Monteriggioni

As you explore Monteriggioni, you will be transported back in time to a medieval village surrounded by intact walls and towers. This small town, located in the heart of Tuscany, is a hidden gem that offers a glimpse into the past. Stepping through the gates, you’ll be greeted by cobblestone streets, charming houses, and a sense of history that permeates the air. Monteriggioni’s attractions include its well-preserved walls, which offer panoramic views of the surrounding countryside, and the Church of Santa Maria Assunta, a beautiful example of medieval architecture. History buffs will appreciate learning about Monteriggioni’s rich history, including its strategic importance during the Middle Ages. Don’t miss the opportunity to explore this enchanting village and learn about its fascinating past.
| Monterrigioni Attractions | Monterrigioni History |
|---|---|
| Well-preserved walls | Strategic importance |
| Church of Santa Maria Assunta | Middle Ages |
| Panoramic views | |
| Charming streets | |
| Sense of history |
Guided Tour of Siena

Set out on a captivating journey through the historic streets of Siena, as a knowledgeable guide leads you through its fascinating treasures. Siena’s cultural heritage is deeply rooted in its historical significance, making it a must-visit destination for history enthusiasts.
Here’s what you can expect during your guided tour of Siena:
Explore Piazza del Campo: Begin your tour at the heart of Siena, where you’ll find the famous Piazza del Campo. This stunning square is known for its unique shell shape and is home to the Palazzo Pubblico, where you can admire beautiful frescoes and climb the Torre del Mangia for panoramic views.
Visit the Siena Cathedral: Admire the architectural marvel of the Siena Cathedral, also known as the Duomo. From its intricate facade to the breathtaking interior, this Gothic masterpiece will leave you in awe. Don’t miss the chance to see the Piccolomini Library, filled with stunning frescoes by Pinturicchio.
Discover the Contrade: Learn about the rich tradition of the Contrade, the 17 unique neighborhoods of Siena. Each Contrada has its own symbol, colors, and history, and the rivalry between them is celebrated during the famous Palio horse race.
With a knowledgeable guide by your side, you’ll gain a deeper understanding of Siena’s cultural heritage and its historical significance. Don’t miss the opportunity to uncover the secrets of this enchanting city.
Discover San Gimignano

After enjoying the cultural heritage of Siena, continue your journey through Tuscany’s medieval wonders by discovering the captivating town of San Gimignano. Known for its well-preserved medieval architecture and stunning skyline, San Gimignano is a must-visit destination. Here is a table highlighting some of the top attractions and the rich history of this enchanting town:
| Attractions | History |
|---|---|
| 1. The Towers of San Gimignano | San Gimignano was once home to 72 towering medieval towers, which were built as symbols of wealth and power. Today, only 14 of these towers remain, creating a unique and picturesque skyline. |
| 2. Piazza della Cisterna | This charming square is the heart of San Gimignano, surrounded by medieval buildings and a well-preserved well. It was once an important meeting point for locals and visitors. |
| 3. Duomo di San Gimignano | The town’s main cathedral is a stunning example of Romanesque architecture. Inside, visitors can admire beautiful frescoes and a marble altar. |
| 4. Museo Civico | Housed in the Palazzo del Popolo, this museum showcases a collection of medieval and Renaissance art, including works by local artists. |
| 5. Rocca di Montestaffoli | This ancient fortress offers panoramic views of the town and the surrounding countryside. It also hosts cultural events and exhibitions throughout the year. |
With its rich history and architectural wonders, San Gimignano is a true gem of Tuscany. Explore its narrow streets, climb the towers, and soak in the medieval atmosphere that transports you back in time.
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Wine Tasting in the Chianti Region

Nestled in the picturesque Chianti region, travelers can indulge in a delightful wine tasting experience that showcases the renowned flavors of Tuscany.
Here are the benefits of wine tasting in the Chianti region:
Immersion in Tuscany’s Wine Culture: Wine tasting allows travelers to enjoy the rich wine culture of Tuscany. They can learn about the region’s winemaking traditions, grape varieties, and unique production methods.
Tasting a Variety of Wines: The Chianti region is home to numerous wineries that produce a wide range of wines. From the famous Chianti Classico to the bold Brunello di Montalcino, wine enthusiasts can taste and compare different varietals and vintages.
Visiting Popular Wineries: The Chianti region is dotted with popular wineries that offer wine tastings and tours. Some of the well-known wineries include Castello di Brolio, Castello di Verrazzano, and Antinori nel Chianti Classico. These wineries not only provide a chance to taste exceptional wines but also offer stunning views of the vineyards and the surrounding countryside.
Wine tasting in the Chianti region is a must-do experience for anyone visiting Tuscany, allowing them to savor the flavors of this renowned wine-producing region.
Common Questions

How Long Does the Full-Day Tour of Central Tuscany From Florence Typically Last?
The full-day tour of central Tuscany from Florence typically lasts around 10-11 hours. Travelers can expect a comprehensive sightseeing itinerary that includes visits to medieval gems like Siena, San Gimignano, and Monteriggioni.
Are Meals Included in the Tour Package?
Meals are not included in the tour package. However, there will be a wine tasting at a local winery in the Chianti region. Travelers with dietary restrictions should plan accordingly.
Is Transportation Provided Throughout the Tour, or Do Travelers Need to Arrange Their Own Transportation?
Transportation is provided throughout the tour, allowing travelers to relax and enjoy the sights. The tour duration is full-day, giving ample time to explore medieval gems like Siena, San Gimignano, and Monteriggioni.
Are There Any Additional Fees or Expenses That Travelers Should Be Aware Of?
There are no additional fees or hidden costs for travelers on the Medieval Gems of Tuscany tour. The price includes transportation, guided tours, and a wine tasting, ensuring a hassle-free and transparent experience.
Is There a Dress Code or Any Specific Attire Requirements for the Tour?
There is no specific dress code or attire requirements for the tour. However, it is recommended to wear comfortable shoes and dress appropriately for the weather, as there will be walking and outdoor activities involved.
The Sum Up

To sum it up, the medieval gems of Tuscany tour offers a captivating journey through the enchanting countryside. From the intact city walls of Monteriggioni to the architectural wonders of Siena, and the striking skyline of San Gimignano, travelers are treated to a truly immersive experience.
To top it all off, a wine tasting in the Chianti region allows visitors to savor the flavors of the Tuscan countryside. Don’t miss out on this unforgettable exploration of Tuscany’s medieval treasures.
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