Siena and San Gimignano, The Glory Of Medieval Age In Tuscany - Scenic Drive through the Chianti Hills

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

Explore Siena and San Gimignano on a private, 8-9 hour tour from Florence, including stops at the stunning Duomo, Piazza del Campo, and the "Manhattan of the Medieval Ages."

Discover the charm of Tuscany’s medieval cities with this private tour from Florence that costs $435.63 per person. Spanning 8 to 9 hours, it offers an intimate experience of Siena and San Gimignano, two towns renowned for their historic architecture, artistic treasures, and vibrant cultures. The tour includes luxury transportation, pickup from Florence, and a personalized guide, making it ideal for those seeking a flexible and enriching day in Tuscany.

While the admission fees to sites like Siena’s Duomo are not included, this tour emphasizes ease and comfort, with a comfortable air-conditioned vehicle and professional driver. The consistent 5-star reviews highlight its popularity, especially for travelers who value customized experiences and local insights. It’s a superb choice for anyone looking to explore Tuscany’s medieval heritage without the hassle of planning every detail or navigating on their own.

Key Points

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany - Key Points

  • Private, personalized tour with a luxury vehicle and English-speaking driver
  • Visits to Siena’s Duomo and Piazza del Campo, plus San Gimignano
  • Approximate duration of 8 to 9 hours, departing at 9:00 am from Florence
  • Includes hassle-free pickup and drop-off in Florence
  • Highly praised by previous guests for knowledgeable guides and flexible arrangements
  • Not included: lunch, admission fees, and optional local guide

Siena’s Duomo: A Masterpiece of Medieval Architecture

The tour begins with a visit to Siena’s Duomo, constructed starting from the 13th century. This famous cathedral is a highlight for its Gothic architecture and intricate marble facade. Inside, visitors find stunning mosaics, sculptures, and artworks, though admission tickets are not included in the tour price. The 30-minute stop allows ample time to admire the cathedral’s grandeur and snap photos of its distinctive exterior.

This site exemplifies Siena’s artistic and religious heritage, making it an essential stop for lovers of history and architecture. The guided commentary enhances understanding, although no guided tour inside is included unless requested. The timing offers a relaxed overview without feeling rushed.

Exploring Piazza del Campo, the Heart of Siena

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany - Exploring Piazza del Campo, the Heart of Siena

Next, the tour guides you to Piazza del Campo, the medieval square renowned for its shell shape and noble palaces. This free 30-minute visit highlights Siena’s social and political history, with the square hosting the famous Palio horse race twice a year. Visitors can stroll along its cobbled streets, take in the historic architecture, and enjoy the lively atmosphere.

The square’s open layout provides excellent photo opportunities, especially of the Town Hall and Torre del Mangia. The overall experience offers insight into Siena’s medieval city life and its significance in Tuscan history.

Scenic Drive through the Chianti Hills

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany - Scenic Drive through the Chianti Hills

One of the tour’s notable features is the panoramic drive through the Chianti hills. This scenic journey showcases Tuscany’s iconic vineyards, olive groves, and rolling landscapes. The luxury air-conditioned vehicle makes the ride comfortable, and the driver provides commentary on the local scenery and wine traditions.

This drive offers a relaxing break from sightseeing, with opportunities for photo stops and to appreciate Tuscany’s natural beauty. Many reviews praise how this part of the tour provides a peaceful contrast to the bustling towns.

San Gimignano: The Manhattan of the Medieval Ages

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany - San Gimignano: The Manhattan of the Medieval Ages

In the afternoon, the tour travels to San Gimignano, known as the “Manhattan of the Medieval Ages” for its dense skyline of medieval towers. The town’s well-preserved towers make it a visual marvel and a UNESCO World Heritage site. Visitors have around 30 minutes to explore its narrow streets, medieval architecture, and local shops.

San Gimignano’s tower houses stand as symbols of medieval wealth and power, and the views from the town walls are particularly admired. The town’s charming atmosphere and historical significance make it a highlight of the tour.

Optional Guided Tour of Siena with a Certified Local Guide

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany - Optional Guided Tour of Siena with a Certified Local Guide

While the self-guided stops provide a good overview, an optional guided tour of Siena with a local certified guide can be requested. This additional service is highly recommended by previous guests for a deeper understanding of Siena’s art, history, and legends. The guides are known for their knowledgeable storytelling and approachable style.

This option enhances the experience, especially for travelers eager to learn more about Siena’s unique landmarks and cultural stories. It’s a valuable upgrade for those with a keen interest in history.

Comfort, Convenience, and Customer Satisfaction

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany - Comfort, Convenience, and Customer Satisfaction

The luxury vehicle ensures a comfortable ride throughout the day, with pickup and drop-off arranged at your Florence accommodation. The driver is fluent in English and provides informative commentary during the drive. The group size remains small and private, adding to the personalized feel.

The reviews consistently highlight the knowledgeable guides, flexibility, and excellent communication from the booking process. Many mention that the driver is patient and engages well with both adults and children, making the trip suitable for families.

Practical Considerations and Booking Tips

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany - Practical Considerations and Booking Tips

The tour is booked on average 123 days in advance, indicating high demand. Most travelers can participate, as the tour requires only moderate walking, but admission fees to sites are not included. Lunch at a winery with Tuscan food and wine pairing is an optional upgrade not included in the base price.

Cancellation is free up to 24 hours before the scheduled start, providing flexibility. Travelers should note that good weather is necessary, as the experience is largely outdoor and scenic.

Why Choose This Tour Over Others?

This private tour stands out for its customization, high customer ratings, and expert driver-guides. It offers a full-day experience covering two iconic towns, with comfortable transport and flexible options. The reviews emphasize the knowledge and professionalism of the staff, making it a reliable choice for those wanting a straightforward, enriching Tuscany trip.

While it doesn’t include all entrance fees or guided tours inside Siena, the option to upgrade provides added value. For travelers seeking personalized service with local insights, this tour delivers.

Siena and San Gimignano: Medieval Treasures in Tuscan Comfort

This private tour offers an excellent way to explore Siena’s artistic treasures and San Gimignano’s towers without the stress of self-driving or group crowds. The 8 to 9-hour itinerary balances sightseeing, scenic drives, and free time for exploration.

It’s particularly suitable for families, history enthusiasts, or anyone wanting a flexible, well-organized day in Tuscany. The high ratings and positive reviews reflect the tour’s reliability and quality.

While some sites require admission fees that are not included, the overall value and experience make this tour a smart choice for experiencing Tuscany’s medieval grandeur.

Ready to Book?

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany



5.0

(8)

100% 5-star

“I would 100% recommend this company.”

— A Tripadvisor Reviewer, May 2025

Frequently Asked Questions

What is the starting time for the tour?
The tour departs from Florence at 9:00 am.

How long does the entire tour last?
The activity runs for approximately 8 to 9 hours.

Is transportation provided?
Yes, a luxury air-conditioned vehicle is included, with pickup and drop-off at your Florence accommodation.

Are meals included?
No, lunch at a winery is an optional upgrade and not included in the base price.

Can I request a local guide in Siena?
Yes, a walking guided tour with a certified local guide can be requested — highly recommended for deeper insights.

What are the main highlights of the tour?
Highlights include Siena’s Duomo, Piazza del Campo, the scenic drive through Chianti, and San Gimignano’s towers.

Is this tour suitable for children?
Yes, previous reviews mention that drivers engage well with families and children, making it suitable for families with kids.

How do I cancel the tour if needed?
Cancellation is free if made more than 24 hours in advance.

What makes this tour different from other Tuscany day trips?
Its private, customizable nature, high customer ratings, and flexibility in stops and optional guides set it apart.