The Siena, San Gimignano, and Monteriggioni Tour from Florence offers an enchanting journey through three historic medieval towns. Participants can explore the UNESCO-listed Piazza del Campo, admire San Gimignano’s iconic towers, and wander the charming streets of Monteriggioni. The tour also includes a delightful wine tasting experience at a rustic Tuscan estate. This 10-hour excursion is perfect for those seeking to enjoy Tuscany’s timeless beauty and traditions. But what else can this tour offer that sets it apart from the rest?
Key Points

- A 10-hour excursion that explores three medieval Tuscan towns – Siena, San Gimignano, and Monteriggioni – with round-trip transportation and an expert multilingual escort.
- Opportunities for wine tasting at a rustic Tuscan estate, where visitors can sample renowned Chianti wines and local snacks.
- Guided tour of Siena’s iconic Piazza del Campo and Piazza del Duomo, highlighting the city’s rich cultural heritage and enduring traditions.
- Discover the well-preserved medieval architecture and towers of San Gimignano, known as the "Manhattan of the Middle Ages."
- Explore the timeless charm and medieval character of Monteriggioni, featuring its well-preserved 13th-century walls and panoramic views of the surrounding countryside.
Tour Overview

This tour offers visitors a chance to explore three of Tuscany’s most captivating medieval towns – Siena, San Gimignano, and Monteriggioni.
Priced from $88.72 per person, the 10-hour excursion includes round-trip transportation, an expert multilingual escort, and opportunities for wine tasting.
Enjoy a 10-hour Tuscan excursion with round-trip transportation, a multilingual escort, and wine tasting opportunities, priced from $88.72 per person.
Highlights include a guided walking tour of Siena’s historic squares, free time to wander the UNESCO-listed San Gimignano, and a visit to the well-preserved hilltop town of Monteriggioni.
With a flexible cancellation policy and the option to reserve now and pay later, this tour provides an immersive Tuscan experience for travelers.
Looking for more options in Florence? We've reviewed plenty of other experiences.
Exploring Monteriggioni

As visitors arrive in Monteriggioni, they’re immediately struck by the town’s well-preserved medieval walls that crown the hilltop. Built in the 13th century, the imposing fortifications encircle the quaint village, transporting travelers back in time.
Strolling along the walls offers panoramic views of the surrounding countryside, dotted with vineyards and olive groves. Within the walls, the main square and narrow streets are lined with historic buildings, cafes, and artisan shops.
Visitors can explore the town’s fascinating history, from its strategic military role to its connections to the famous Medici family. Monteriggioni’s timeless charm and well-preserved medieval character make it a highlight of the Tuscan tour.
Guided Tour of Siena

The guided tour of Siena begins with a visit to the iconic Piazza del Campo, the city’s main square and a UNESCO World Heritage site. Here, the guide shares the history and significance of this stunning medieval plaza, known for its unique shell-like shape.
The tour then moves to the Piazza del Duomo, home to Siena’s imposing cathedral, a masterpiece of Italian Gothic architecture. Visitors explore the cathedral’s magnificent interior, marveling at its stunning marble façade and intricate frescoes.
Throughout the tour, the guide provides insights into Siena’s rich cultural heritage and the city’s enduring traditions.
Discovering San Gimignano

After exploring the historic Siena, the tour heads to the captivating town of San Gimignano, a UNESCO World Heritage Site renowned for its well-preserved medieval architecture and iconic skyline of towering stone structures.
Visitors are free to wander the charming streets, admiring the 14 medieval towers that have earned San Gimignano the nickname "the Manhattan of the Middle Ages."
The town is also famous for its Vernaccia white wine, which can be sampled at local vineyards.
With ample time to discover San Gimignano’s unique character, the tour offers an immersive experience in this enchanting Tuscan destination.
More Great Tours NearbyWine Tasting Experience

One highlight of the tour is the wine tasting experience at a rustic Tuscan wine estate. Guests have the opportunity to sample the region’s renowned Chianti wines and learn about the winemaking process.
The tasting is accompanied by local snacks and olive oils, providing a well-rounded sensory experience. The serene setting allows visitors to enjoy the traditions and flavors of the Chianti countryside.
This excursion not only delights the palate but also offers a glimpse into the cultural heritage that has shaped the winemaking traditions of the region.
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Transportation and Guides

Roundtrip transportation in an air-conditioned bus takes travelers from Florence to the historic towns of Siena, San Gimignano, and Monteriggioni. Experienced, multilingual guides accompany guests throughout the day, providing insights and expertise in English and Spanish. Their enthusiasm and knowledge enhance the overall experience.
| Experience Level | Language Skills |
| —————- | ————— |
| Expert | English, Spanish|
| Passionate | Engaging, Informative|
| Dedicated | Attentive, Flexible|
| Knowledgeable | Historical, Cultural|
The seamless coordination of transportation and guides ensures a memorable, enriching tour through Tuscany’s picturesque landscapes and medieval landmarks.
Meeting Point and Important Details

The tour meeting point is at the Tours & News Kiosk located in Piazzale Montelungo Bus Terminal, just a 5-10 minute walk from Santa Maria Novella Train Station.
Look for personnel in fuchsia jackets with clipboards who’ll be there to guide you.
This tour isn’t suitable for wheelchair users, and large bags or luggage aren’t allowed.
Travelers should plan accordingly and leave bulky items behind.
Following these meeting point instructions and guidelines will ensure a smooth start to the day’s excursion to Siena, San Gimignano, and Monteriggioni.
Customer Feedback

Travelers have shared overwhelmingly positive experiences about this tour to Siena, San Gimignano, and Monteriggioni from Florence.
With a 4.6/5 overall rating based on 5 reviews, the tour has exceeded expectations. Reviewers praised the knowledgeable guides, stunning sights, and ample free time to explore at leisure.
One guest noted the "incredible day filled with picturesque medieval towns and delicious local wine."
Another highlighted the "great balance of guided tours and independent exploration."
Customers consistently recommend this immersive day trip for its combination of history, culture, and scenic beauty in the Tuscan countryside.
Ask Away
What if I Have Dietary Restrictions for the Wine Tasting?
If the customer has dietary restrictions, they should notify the tour operator in advance. The operator can accommodate alternative options or provide different food items during the wine tasting experience.
Can I Bring My Pet on the Tour?
Unfortunately, pets are not allowed on this tour. The tour operator’s policy states that only service animals are permitted. Passengers are advised to make alternative arrangements for their pets during the tour duration.
Is There a Discount Available for Seniors or Students?
The tour provider doesn’t offer any discounted rates for seniors or students. The standard price of $88.72 per person applies to all participants regardless of age or student status. Discounts may be available through third-party booking platforms.
How Punctual Do I Need to Be at the Meeting Point?
Punctuality is important as the tour departs on time. Guests should aim to arrive at the meeting point 10-15 minutes early to ensure they don’t miss the bus. Late arrivals may not be accommodated.
Can I Extend My Stay in Any of the Towns?
Customers can extend their stay in any of the towns visited during the tour. However, it’s important to note that the tour itself is a set itinerary and doesn’t provide additional time for individual exploration beyond the scheduled free time.
Final Words
The Siena, San Gimignano, and Monteriggioni Tour from Florence offers a captivating journey through Tuscany’s medieval gems. Travelers can explore UNESCO-listed wonders, admire iconic towers, and indulge in a Tuscan wine tasting – all while seeing the region’s timeless beauty and traditions. With knowledgeable guides and comfortable transportation, this 10-hour excursion is an ideal way for visitors to discover the enchanting heart of Italy.
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