Tuscany is a captivating region of Italy, renowned for its medieval wonders and picturesque landscapes. This small-group tour provides travelers with a comprehensive exploration of its highlights, from the charming streets of Siena to the iconic Leaning Tower of Pisa. Led by an experienced guide, guests will enjoy the region’s rich history and culture, enjoying a delightful Tuscan lunch and wine tasting at a Chianti winery. With its well-rounded itinerary and personalized experience, this tour promises to be a memorable journey through one of Italy’s most captivating destinations. What awaits those who embark on this Tuscany adventure?
Key Points

- The tour covers the highlights of Tuscany, including medieval centers of Siena and San Gimignano, a Chianti winery visit, and the Leaning Tower of Pisa.
- Guided walking tours in Siena and San Gimignano provide insight into the history and architecture of these well-preserved medieval towns.
- The Chianti winery tour and wine tasting allow participants to experience the region’s renowned wines and local cuisine.
- The tour is led by an English-speaking guide and transported by an air-conditioned minivan for a comfortable and convenient experience.
- The itinerary culminates with a visit to the iconic Leaning Tower of Pisa, a must-see highlight of the tour.
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Contents
- Key Points
- Tour Overview
- Inclusions
- Meeting Point
- Itinerary
- Explore Siena
- Visit San Gimignano
- Tour a Chianti Winery
- See the Leaning Tower of Pisa
- Frequently Asked Questions
- What Is the Duration of the Tour?
- Can the Tour Be Customized for Private Groups?
- Is There a Dress Code for the Winery Visit?
- Are Gratuities for the Guide and Driver Included?
- Can Children Participate in the Wine Tasting?
- Recap
- Our Top Picks in Florence
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Tour Overview
Covering Tuscany’s highlights, the full-day Small-Group Tuscany Grand Tour departs from Florence and visits the medieval centers of Siena and San Gimignano.
The tour includes a lunch and wine tasting in the Chianti region, and culminates with a stop at the iconic Leaning Tower of Pisa.
Travelers will enjoy a guided walking tour of Siena’s historic center, marvel at the medieval towers of San Gimignano, and savor a typical Tuscan lunch paired with fine Chianti wines at a local winery.
The tour is led by an English-speaking guide and transportation is provided in a comfortable air-conditioned minivan, ensuring a seamless and enjoyable experience exploring Tuscany’s renowned landmarks and countryside.
You can also read our reviews of more tours and experiences in Florence.
Inclusions

The tour includes round-trip transportation by air-conditioned minivan, a guided walking tour of Siena, a winery tour and wine tasting, a visit to the medieval village of San Gimignano, and a stop at the Leaning Tower of Pisa and Piazza dei Miracoli.
An English-speaking guide accompanies travelers throughout the day, providing insights and commentary.
Lunch at a winery in the Chianti region is also included, offering a taste of traditional Tuscan cuisine.
With these inclusions, the Small-Group Tuscany Grand Tour provides a comprehensive exploration of the region’s highlights, allowing visitors to enjoy the history, culture, and flavors of Tuscany.
Meeting Point

The tour meets at the FLORENCETOWN BOOKING OFFICE, located at Piazza Mentana 2red in Florence. Travelers should arrive 15 minutes before the scheduled departure time.
This meeting point is conveniently located and easy to find, ensuring a smooth start to the day’s adventure.
Once the group has gathered, the air-conditioned minivan will depart for the day’s itinerary, which includes visits to the medieval towns of Siena and San Gimignano, a wine tasting and lunch in the Chianti region, and a stop at the iconic Leaning Tower of Pisa.
With an English-speaking guide leading the way, participants can look forward to a comprehensive and enjoyable exploration of Tuscany’s highlights.
Itinerary

The Tuscany Grand Tour takes participants on a captivating journey through the region’s iconic landmarks and picturesque landscapes. It starts with an exploration of Siena, where the group will wander through the charming medieval center, including the renowned Piazza del Campo. Next, they’ll visit the medieval village of San Gimignano, known for its well-preserved towers that dot the skyline. The tour then moves on to a Chianti winery, where travelers can indulge in a delightful Tuscan lunch and savor the region’s renowned wines. Finally, the group will witness the renowned Leaning Tower of Pisa in all its glory at the Piazza dei Miracoli.
| Destination | Key Highlights |
|---|---|
| Siena | Explore the medieval center, including Piazza del Campo |
| San Gimignano | Marvel at the well-preserved medieval towers |
| Chianti Winery | Enjoy a Tuscan lunch and wine tasting |
| Pisa | See the iconic Leaning Tower in Piazza dei Miracoli |
Explore Siena

Visitors on the Tuscany Grand Tour begin their exploration of Siena by seeing the city’s well-preserved medieval center, where they can admire the striking Piazza del Campo, the heart of the historic city.
This vast, fan-shaped square is renowned for its unique architecture and the annual Palio horse race.
The group then proceeds to the Siena Cathedral, a stunning Gothic masterpiece featuring ornate marble facades and intricate mosaics.
As they wander through the narrow streets, they’ll discover charming shops, cafes, and the remnants of Siena’s rich cultural heritage, providing a glimpse into the city’s illustrious past.
Visit San Gimignano

After exploring the medieval wonders of Siena, the group then travels to the enchanting hilltop town of San Gimignano, known for its well-preserved towers that dot the skyline and offer panoramic views of the surrounding Tuscan countryside. As the van ascends the winding roads, the group eagerly anticipates the charming medieval architecture and historic atmosphere. Upon arrival, the guide leads them on a walking tour through the town’s narrow streets, pointing out the impressive towers and explaining their significance in the town’s history. The group has the opportunity to wander independently, discovering quaint shops, sampling local delicacies, and admiring the breathtaking vistas from the top of the towers.
| Highlights of San Gimignano | ||
|---|---|---|
| Iconic Medieval Towers | Stunning Views | Charming Shops |
| Historic Architecture | Local Cuisine | Peaceful Piazzas |
Tour a Chianti Winery

Next, the group heads to a renowned Chianti winery, where they’ll embark on a guided tour and have the opportunity to savor the region’s renowned wines.
During the winery visit, the knowledgeable guide provides insights into the winemaking process, from grape cultivation to barrel aging. Guests explore the cellars and learn about the unique terroir that gives Chianti wines their distinctive character.
The highlight of the experience is the tasting, where they’ll sample a selection of the winery’s finest offerings, paired with a delicious Tuscan lunch. This intimate encounter with the Chianti winemaking tradition is a true highlight of the Tuscany Grand Tour, offering a deep appreciation for the region’s rich cultural heritage.
See the Leaning Tower of Pisa

The final stop on the Tuscany Grand Tour takes guests to the iconic Leaning Tower of Pisa, where they’ll have the opportunity to marvel at this architectural wonder set within the stunning Piazza dei Miracoli.
Visitors can:
- Admire the tower’s distinctive tilt, a result of the soft ground it was built upon.
- Explore the surrounding Piazza dei Miracoli, home to the Pisa Cathedral and Baptistery.
- Capture the perfect photo, leaning alongside the tower for a truly memorable souvenir.
With its history, beauty, and the chance to take that classic ‘holding up the tower’ photo, the Leaning Tower of Pisa is an unforgettable highlight of the Tuscany Grand Tour.
Frequently Asked Questions
What Is the Duration of the Tour?
The tour is a full-day excursion, allowing ample time to explore Tuscany’s highlights. Travelers can expect to spend approximately 8-9 hours on the tour, with a packed itinerary covering medieval towns, a winery, and the iconic Leaning Tower of Pisa.
Can the Tour Be Customized for Private Groups?
The tour can be customized for private groups. Travelers can work with the tour operator to adjust the itinerary and inclusions to meet their specific needs and preferences.
Is There a Dress Code for the Winery Visit?
There’s no strict dress code for the winery visit, but visitors are advised to dress comfortably and appropriately for a relaxed, informal setting. Casual attire like jeans, t-shirts, and comfortable shoes is generally suitable.
Are Gratuities for the Guide and Driver Included?
Gratuities for the guide and driver are not included in the tour price. Participants are welcome to provide tips at their discretion based on the quality of service received during the Small-Group Tuscany Grand Tour.
Can Children Participate in the Wine Tasting?
Children are not permitted to participate in the wine tasting portion of the tour. However, the tour does include an infant car seat option, allowing families with young children to join the excursion.
Small-Group Tuscany Grand Tour: Siena, San Gimignano, Chianti and Pisa
“Lots of places to see and activities to do in one day. Our guide Gabriel is wonderful. Highly recommended.!”
Recap
This small-group Tuscany tour provides an immersive experience of the region’s medieval wonders.
Travelers will explore the charming streets of Siena, marvel at the iconic towers of San Gimignano, indulge in a Tuscan lunch and wine tasting, and visit the legendary Leaning Tower of Pisa – all while led by an English-speaking guide.
It’s a well-rounded exploration of Tuscany’s history, culture, and stunning landscapes.
























