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Discover Tuscany with this full-day tour from Florence, including Pisa's Piazza dei Miracoli, Chianti wine tasting, Siena's historic streets, and Monteriggioni Castle.

This Tuscany Grand Tour from Florence offers an engaging way to see some of Italy’s most iconic sights in a single day. Priced at $346.02 per person, the tour lasts about 10 to 11 hours and includes visits to Pisa, Chianti wine estates, Siena, and Monteriggioni Castle. It departs at 8:00 AM from Piazza degli Antinori in Florence and is perfect for travelers seeking a comprehensive taste of Tuscany’s famous landscapes, towns, and wines.
While the tour provides a well-rounded experience, it’s worth noting that time in the car can be lengthy, especially between Pisa and Chianti. The tour is ideal for those who want a guided, organized day with transportation included, but it may feel rushed for visitors who prefer more time in each location. With a maximum group size of 8 travelers, it offers a more intimate setting compared to larger bus tours.

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The tour begins with a scenic ride through Tuscany’s lush landscapes, setting the tone for the day. The journey from Florence to Pisa takes about 1 hour and 15 minutes, giving ample opportunity to enjoy the rolling hills and vineyards. This drive is part of the experience, allowing you to relax and take in the views before exploring the city’s highlights.
Traveling in a comfortable vehicle, the small group format ensures a relaxed atmosphere and personalized attention. The driver is English-speaking, providing a friendly and informative ride without being a guide, so guests can enjoy the scenery en route.

The first stop is Pisa’s Piazza dei Miracoli, a UNESCO World Heritage site. Here, you have about 1 hour and 15 minutes to admire the Leaning Tower of Pisa, Duomo, and Baptistery. The tour allows ample free time to take photos of these iconic monuments and appreciate the architecture.
This stop captures the essence of Pisa’s famous leaning tower, which remains a marvel of engineering. Visitors can marvel at the intricate façade of the Duomo and the beauty of the Baptistery, all within walking distance. The tour doesn’t include tickets, so access to the interior of the cathedral or tower is not part of the package.

After Pisa, the journey continues to Castellina In Chianti, the heart of the Chianti Classico region. Here, a sommelier or local wine producer welcomes the group for a wine estate tour, lasting about 2 hours. This experience includes a wine tasting session, showcasing Italy’s renowned Chianti wines.
Guests enjoy a local lunch featuring homemade pasta, artisanal cheese, and cured meats — all paired with the estate’s wines. The tasting offers insight into Tuscany’s wine-making traditions and the region’s unique flavors.
One important note: according to reviews, the driver might rush guests during the tasting, limiting the opportunity to fully enjoy the experience. The quality of the wine and food is praised as excellent, and the setting provides lovely views of the Tuscan countryside.

Next, the tour takes you to Siena, a city famed for its medieval charm. The guided walk lasts about 1 hour and 15 minutes, leading visitors through Siena’s Duomo square and Piazza del Campo. The guide highlights the city’s history, architecture, and local stories.
In Siena, guests get a chance to see the Siena Cathedral, a stunning example of Gothic architecture, and learn about the city’s historic significance. The walking tour is designed to reveal Siena’s hidden gems and give context to its well-preserved medieval streets.
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The final stop before returning to Florence is Monteriggioni Castle, a walled fortress that dates back to the medieval period. The group has about 20 minutes here to take photos and appreciate the castle’s impressive walls and towers.
This scenic photo stop captures the historic essence of Tuscany’s fortified villages, offering picturesque views that are perfect for memories or sharing online.

This Tuscany Grand Tour includes round-trip transportation from Florence, allowing guests to relax without the hassle of driving. The package features free time at Pisa’s Piazza dei Miracoli and the Duomo, a wine estate tour and tasting, a Tuscan lunch, and a guided walk in Siena.
Mineral water is provided for each passenger, and the tour can accommodate dietary restrictions such as vegetarian, vegan, or gluten-free options. An English-speaking driver ensures smooth transportation, although the driver is not a guide.
The tour operates with a maximum of 8 travelers, making it a more intimate experience compared to larger groups, and group discounts are available.

While most aspects are praised, some feedback highlights potential challenges. The long drives between Pisa and Chianti can feel tiring, and time constraints during tastings and Siena’s visit may leave some wishing for more leisurely exploration. One review mentions feeling rushed during the wine tasting, and another notes that the Siena tour was not as engaging as hoped.
Despite these points, the knowledgeable guides and excellent wine and food are notable strengths, creating a balanced experience for those wanting a comprehensive Tuscany day trip.
This full-day tour from Florence offers an efficient way to see Pisa’s iconic monuments, sample Chianti wines, explore Siena’s historic streets, and enjoy a medieval castle. It’s a solid choice for travelers who value guided experiences, quality food and wine, and the convenience of organized transport.
While the driving time can be substantial and some may find the schedule a bit tight, the small group size and personalized touches make this tour an attractive option. It suits those eager to experience multiple highlights in one day without the hassle of planning individual visits.
“The tour was great. The driver, Sal, was engaging and flexible to our request. We stopped few times along the way for a photo moment.”
What is included in the tour?
The tour includes round-trip transportation from Florence, free time at Pisa and Siena, a wine estate tour and tasting, a Tuscan lunch, a guided walk of Siena, and a photo stop at Monteriggioni. Mineral water is also provided.
How long is the drive between stops?
The drive from Florence to Pisa takes about 1 hour and 15 minutes, and the trip from Chianti to Siena is included in the overall schedule, with some longer stretches like Pisa to Chianti.
What is the group size?
The maximum group size is 8 travelers, ensuring a more personalized experience.
Can dietary restrictions be accommodated?
Yes, the tour can accommodate vegetarian, vegan, gluten-free, and other dietary restrictions.
Is there free cancellation?
Yes, free cancellation is available up to 24 hours before the tour start time.
What are the main highlights of the tour?
Highlights include Pisa’s Piazza dei Miracoli, Chianti wine tasting, Siena’s Duomo and Piazza del Campo, and a photo stop at Monteriggioni.
Are tickets to the monuments included?
No, entry to Pisa’s cathedral or tower is not included; the tour offers free time to admire the exterior.
What should I bring?
Bring comfortable shoes for walking, a camera, and any dietary needs, as well as a love for wine and history.
Is this tour suitable for children?
Most travelers can participate, but given the walking and driving, it’s best suited for older children or teens.
What is the price of the tour?
The price is $346.02 per person, which includes most experiences and transportation but excludes gratuities.
This Tuscany Grand Tour from Florence offers a well-organized, enriching day through some of Italy’s most beautiful and historic sites, perfect for those eager to explore Tuscany without the hassle of planning each detail.