Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Key Points

• Comprehensive day trip covering Pisa, Siena, and San Gimignano from Florence
• Includes a traditional Tuscan lunch with wine pairing (if selected)
• Expert guides lead walking tours, providing engaging insights
• Free time in Pisa and San Gimignano for independent exploration
• Transportation on a comfortable, air-conditioned coach with free Wi-Fi
• Cost-effective at approximately $75.47 per person, booked 41 days in advance on average

The Pisa, Siena and San Gimignano Day Trip offers a well-rounded look at some of Tuscany’s most iconic spots. For just over $75, this 12-hour tour takes you through historic towns, UNESCO World Heritage sites, and rolling countryside, with a tasty Tuscan lunch included (if you opt for the wine pairing). The tour is particularly suited for those who want to see multiple towns efficiently, with guided insights and free time to explore on your own. One notable limitation is the length of the day, requiring moderate walking; also, the semi-independent option excludes guided tours in Siena and access to Siena Cathedral.

From Florence to Siena’s Medieval Charm

The journey begins early at Piazzale Montelungo in Florence, where a comfortable coach awaits. The trip through Tuscany’s rolling hills lasts about one hour, with a guide sharing fascinating facts about Siena along the way. Once in Siena, the group is led through its picturesque streets to Piazza del Campo, the heart of the city and scene of the famous Palio horse race.

In Siena, a professional guide provides a detailed walking tour of the UNESCO-listed city, highlighting key sights and local stories. The tour lasts about two hours, giving a thorough introduction to Siena’s history and architecture. Visitors are then taken to the Siena Cathedral, known for its striking black and white marble façade and breathtaking interior. Entry to the cathedral is included if the “with Cathedral” option is chosen, but those on the semi-independent tour explore on their own without a guide.

Exploring Piazza del Campo and Torre del Mangia

A highlight in Siena is the Piazza del Campo, a spacious shell-shaped square where locals gather and the Palio takes place twice a year. The guide shares stories about the square’s history, and visitors can spend around 30 minutes soaking in the lively atmosphere. Adjacent is the Torre del Mangia, Siena’s tall clocktower, which dominates the skyline. Visitors outside the tower get a quick look in about 15 minutes, learning about its significance and architecture, though access to climb the tower is not included.

Siena Cathedral and Free Exploration

Following the guided tour, guests have about 20 minutes to visit the interior of Siena Cathedral independently. Inside, they can admire frescoes and artworks, including the famous Piccolomini Library. Access to the cathedral is included if the selected option covers admission. Those on the “without Cathedral” or semi-independent options do not visit the interior but can still walk around the stunning square and city streets at leisure.

Lunch and Wine Tasting at a Tuscan Vineyard

After Siena, the tour heads to a family-owned winery located about one hour from San Gimignano. The scenic drive offers views of sunny hills, olive groves, and vineyards. Here, participants indulge in a three-course Tuscan lunch featuring regional dishes like bruschetta, pasta, cheese, meat, and dessert, paired with high-quality wines—if the lunch with wine pairing is selected.

The wine tasting is a key feature, praised for showcasing Tuscan varietals in an authentic setting. The lunch and tasting last about two hours, providing a relaxing break amid the countryside’s beauty.

Discovering the Towers of San Gimignano

Following lunch, the group visits the medieval hilltop town of San Gimignano, famous for its thirteen remaining towers. The guide leads visitors to a panoramic viewpoint, offering sweeping views of the Tuscan landscape and photo opportunities. Visitors then have around one hour to explore independently, wandering the charming narrow streets lined with shops and cafes.

San Gimignano’s Piazza della Cisterna is a focal point, where visitors can relax with gelato or coffee and enjoy the picturesque surroundings. Inside the Collegiata di Santa Maria Assunta, colorful frescoes decorate the interior, and entry is included if the “with Duomo” option is chosen. Otherwise, visitors can appreciate the exterior and ambiance.

Traveling to Pisa and the Leaning Tower

After San Gimignano, the coach departs for Pisa, a journey of around one hour. The group then arrives at the Square of Miracles, home to the Leaning Tower, the Pisa Baptistery, and the Cathedral. You have approximately an hour for sightseeing, with ample time for photos, as the iconic Leaning Tower is the most photographed site.

Guests can choose to climb the Leaning Tower if the “not included” admission is paid, which offers stunning panoramic views of Pisa and the surrounding countryside. The Pisa Cathedral’s Romanesque architecture is also worth a quick visit if time allows.

Return to Florence with Lasting Memories

The journey back to Florence takes about one hour, with the coach providing free Wi-Fi and a comfortable environment to relax. The tour concludes at the original meeting point, Piazzale Montelungo, around late afternoon, after a full day of sightseeing in some of Tuscany’s best-known towns.

Practical Details and Tips

The tour starts promptly at 7:30 am, and guests should be prepared for moderate walking, including cobblestone streets and some inclines. The tour involves a total of around 12 hours, making it suitable for those comfortable with long days on their feet. Access to Siena Cathedral requires adherence to a dress code—shoulders and knees covered—and the semi-independent option does not include guided tours or cathedral access.

The cost for this tour is approximately $75.47 per person, with bookings generally made 41 days in advance. The tour is operated by Ciao Florence Tours Srl, known for their professional guides and comfortable coaches.

Is This Tour Right For You?

This trip is ideal for travelers who want a rundown of Tuscany in a single day, with convenient transportation, guided insights, and a delicious lunch. It suits those who appreciate guided tours with free time for personal exploration. However, it may be less suitable for those with mobility issues or those seeking a more relaxed pace, given the long hours and walking involved.

The Sum Up: A Practical Day in Tuscany’s Historic Towns

The Pisa, Siena, and San Gimignano Day Trip offers a solid balance of guided sightseeing, independent exploration, and a taste of authentic Tuscan cuisine and wine. Its well-organized itinerary ensures visitors see the most famous sights efficiently, with highlights like the Leaning Tower of Pisa and San Gimignano’s towers. The included lunch and wine tasting enhance the experience, providing a true flavor of the region.

While the long day and walking demands require some physical fitness, this tour provides good value and a memorable overview of Tuscany’s charm. It’s particularly well-suited for those short on time but eager to see multiple highlights with expert guidance and insider stories. For a practical, enriching day trip from Florence, this tour offers a reliable and enjoyable option.

Frequently Asked Questions

Does the tour include hotel pickup and drop-off?
No, hotel pickup and drop-off are not included; guests meet at Piazzale Montelungo in Florence.

Can I climb the Leaning Tower of Pisa?
Climbing the tower is possible only if the admission fee is paid and if no queue delays the process; it is not included in the tour price.

Is the lunch at the winery included?
Yes, if the lunch and wine pairing option is selected, it includes a three-course Tuscan meal with wine.

How much walking is involved?
The tour involves a moderate amount of walking, including cobblestone streets and some inclines, suitable for most but possibly challenging for those with mobility issues.

What is the maximum group size?
The tour accommodates up to 63 travelers, ensuring a lively but manageable experience.

Can I customize the tour, such as skipping certain stops?
The itinerary is fixed, but some options, like semi-independent tours, exclude guided visits or cathedral access, offering some flexibility.