If you’re looking to escape Florence for a day, the Siena, San Gimignano & Monteriggioni tour might just be the ticket. This journey takes you through some of Tuscany’s most charming medieval towns, each with its own unique vibe. From the stunning architecture of Siena to the iconic towers of San Gimignano, there’s plenty to explore. Plus, who can resist a little wine tasting? Stick around to find out what else this tour has to offer.
Key Points

- The tour lasts approximately 11 hours, departing from Florence to explore Tuscany’s medieval towns.
- Key highlights include visits to Monteriggioni, Siena, San Gimignano, and a Chianti farm for wine tasting.
- Enjoy 1 hour in Monteriggioni, 2 hours in Siena, and 1.5 hours in San Gimignano.
- Wine tasting at a Chianti farm features local reds paired with snacks in a scenic countryside setting.
- The tour costs €65.00 per person with free cancellation up to 24 hours in advance.
Overview of the Tour

If you’re eager to explore some of Tuscany’s most charming medieval towns, the Siena, San Gimignano & Monteriggioni Tour is a perfect choice.
This full-day adventure, lasting about 11 hours, takes you from Florence to stunning locations that showcase the region’s rich history.
For just €65.00 per person, you can dive into Siena’s Gothic architecture, wander the narrow streets of San Gimignano, and appreciate the intact walls of Monteriggioni.
Plus, with free cancellation up to 24 hours in advance and the option to reserve now and pay later, planning your Italian getaway’s never been easier!
Looking for more options in Florence? We've reviewed plenty of other experiences.
Itinerary Highlights

The itinerary for the Siena, San Gimignano & Monteriggioni Tour is packed with fascinating experiences that highlight Tuscany’s medieval charm. Travelers explore stunning towns, enjoy breathtaking landscapes, and savor local wines. Here’s a quick snapshot of what to expect:
| Stop | Highlights | Duration |
|—————-|—————————————|——————|
| Monteriggioni | Intact medieval walls, free time | 1 hour |
| Siena | Piazza del Campo, Gothic architecture | 2 hours |
| San Gimignano | Narrow streets, UNESCO site | 1.5 hours |
| Chianti Farm | Wine tasting, local snacks | 1.5 hours |
This tour’s got it all!
Exploring Siena

Siena’s charm captivates visitors with its stunning Gothic architecture and vibrant piazzas.
As they wander through the historic streets, they can’t help but admire the breathtaking Piazza del Campo, famous for its unique shell shape.
The iconic Palazzo Pubblico stands tall, showcasing intricate artworks that tell the city’s rich history.
Visitors often take a moment to soak up the lively atmosphere, enjoying a gelato or sipping coffee at a quaint café.
With narrow alleys leading to hidden gems, Siena invites exploration, making it a must-see on any Italian adventure.
It’s a place where history and culture come alive!
Discovering San Gimignano

Just a short drive from Siena, San Gimignano awaits with its medieval charm and stunning towers.
This UNESCO World Heritage Site boasts narrow streets lined with quaint shops and local eateries, inviting visitors to explore and indulge.
The iconic skyline, featuring its towering medieval buildings, tells tales of the town’s rich history.
The striking skyline of San Gimignano, adorned with majestic medieval towers, unveils the captivating stories of its historic past.
Strolling through the cobblestone streets, travelers can savor gelato from award-winning shops or sip on local wines.
San Gimignano’s lush landscapes provide a picturesque backdrop, perfect for those Instagram moments.
It’s a delightful stop that captures the essence of Tuscany’s enchanting past and vibrant culture.
More Great Tours NearbyThe Charm of Monteriggioni

Nestled atop a hill, Monteriggioni captivates visitors with its well-preserved medieval charm and stunning views of the surrounding countryside. This small, enchanting town boasts ancient walls and picturesque streets perfect for leisurely exploration. Visitors often enjoy the vibrant local culture and history that breathes life into every corner. Check out this quick guide to what makes Monteriggioni special:
| Feature | Description | Highlights |
|———————-|———————————|—————————|
| Medieval Walls | Impressive fortifications | Stunning views |
| Local Cuisine | Traditional Tuscan dishes | Cozy trattorias |
| Art & Culture | Historic churches and museums | Engaging local events |
| Scenic Surroundings | Picturesque landscapes | Great photo opportunities |
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Wine Tasting Experience

Wine tasting in the Chianti region is a delightful adventure that tantalizes the senses. Guests get to sip on exquisite local wines while soaking in the stunning countryside views.
At a charming Chianti farmhouse, they’ll sample a selection of reds, paired perfectly with delicious snacks. Each sip tells a story of the land, the grapes, and the tradition behind them. Knowledgeable hosts share insights, making it an educational experience too.
Whether you’re a seasoned wine enthusiast or just starting out, this tasting offers a relaxed atmosphere to enjoy good company and indulge in the rich flavors of Tuscany. Cheers to that!
Transportation Details

Getting to the Siena, San Gimignano & Monteriggioni Tour is a breeze, thanks to the convenient round-trip transportation provided in an air-conditioned bus.
Travelers meet at Piazza Montelungo, just a short 5-10 minute stroll from Santa Maria Novella Train Station. Once there, they’ll spot the friendly staff in their bright fuchsia Ciaoflorence jackets, ready to assist.
The bus ride allows guests to relax and soak in the beautiful Tuscan landscape, making the journey part of the adventure. With comfortable seating and a smooth ride, it’s the perfect way to kick off an unforgettable day exploring Italy’s medieval gems!
Customer Reviews and Ratings

While exploring the Siena, San Gimignano & Monteriggioni Tour, travelers often rave about their experiences, reflected in the tour’s impressive overall rating of 4.6 out of 5 based on 2,437 reviews.
People love:
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The knowledgeable and engaging guides who bring history to life.
-
Beautiful landscapes that make for perfect photo ops.
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The charming medieval towns that feel like stepping back in time.
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The delightful wine tasting that complements the stunning views.
Though some have mixed feelings about Monteriggioni, the overall consensus is clear: this tour delivers unforgettable memories and fantastic value!
Since Your Asked

What Should I Wear for the Tour?
For the tour, she should wear comfortable shoes for walking, light layers for changing weather, and a hat or sunglasses for sun protection. A small backpack can hold essentials like water and snacks.
Are There Vegetarian Options During Wine Tasting?
Yes, there’re vegetarian options available during the wine tasting. Tour providers ensure that everyone enjoys the experience, so they’ll have tasty snacks suitable for vegetarians, making sure no one’s left out of the fun!
Is This Tour Suitable for Children?
This tour’s perfect for families! Kids will love exploring the medieval towns and tasting local goodies. With engaging guides and plenty of free time, it’s a fantastic adventure for children and adults alike.
Can I Bring My Pet on the Tour?
Unfortunately, pets aren’t allowed on the tour. They want to ensure everyone enjoys the experience without distractions. However, it’s best to check directly with the tour provider for any exceptions or specific policies.
Are There Any Age Restrictions for Wine Tasting?
There aren’t any strict age restrictions for wine tasting, but participants usually need to be 18 or older. It’s a fun experience, so younger guests might just enjoy the snacks and scenery instead!
The Last Word
In just a day, this tour from Florence offers an unforgettable taste of Tuscany’s medieval magic. With enchanting towns like Monteriggioni, the stunning architecture of Siena, and the delightful gelato in San Gimignano, there’s something for all. Plus, the wine tasting at a Chianti farm adds a perfect touch to the experience. For just €65.00, it’s a steal! So, if you’re ready for an adventure filled with history, beauty, and flavor, this tour’s a must-do!
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