Pisa and Florence Private Tour with Wine Tasting

Travel to Italy’s celebrated cities of Pisa and Florence in just one day with this private 9-hour tour led by knowledgeable guides. Starting from Livorno, the tour costs $1,299.46 per group, accommodating up to 7 people. This fully private experience ensures personalized attention, smooth transport, and the flexibility to explore at your own pace. It includes a visit to the Square of Miracles, the Leaning Tower, panoramic views of Florence, and a wine tasting in the Chianti hills. The tour is ideal for travelers seeking a comprehensive taste of Tuscany’s treasures in a single day, with many booking well in advance — on average 128 days ahead.

While the tour offers a rich itinerary and expert guidance, it’s worth considering that lunch is not included, so you might want to plan for that. The tour’s emphasis on cultural highlights, scenic drives, and a private wine tasting makes it a solid choice for those wanting an intimate, hassle-free experience of Italy’s artistic and culinary heartlands.

Key Points

• Full-day private tour exploring Pisa and Florence from Livorno
• Includes transportation, guide, and wine tasting in Chianti hills
• Visit key sites like the Square of Miracles, Leaning Tower, Palazzo Vecchio, and Ponte Vecchio
• Tour duration is approximately 9 hours, with hotel or port pickup and drop-off
• Exclusive wine and olive oil tasting at Fattoria San Michele a Torri
• All major stops are private with guided insights and scenic views

Starting Point and Transport in Livorno

This tour departs from the Port of Livorno at Piazzale dei Marmi, 12. It features luxury Mercedes vehicles or minivans equipped with air conditioning and WiFi for a comfortable ride. The private transport guarantees a smooth experience, with hotel or port pickup and drop-off included, eliminating the stress of coordinating public transport or navigating unfamiliar roads. The vehicle is spacious enough for up to 7 guests, making the journey intimate and relaxing.

The driver/guide not only handles logistics but also provides live commentary throughout the day, sharing insights into Tuscan history, architecture, and local culture. This personalized approach helps maximize your time at each site, with a flexible schedule tailored to your interests.

Exploring Pisa’s Historic Heart: Piazza dei Cavalieri

The first stop is Piazza dei Cavalieri, Pisa’s Renaissance political center. This elegant square is free to enter and offers stunning architecture by Vasari, including the Palazzo della Carovana and the Palazzo dell’Orologio. The sculpture of Cosimo I de Medici, prominently displayed with a shell-shaped fountain, highlights Pisa’s historical naval strength.

The Church of Santo Stefano dei Cavalieri nearby displays Ottoman banners and ornate interiors, though most buildings are not open to the public. The open-air setting provides a peaceful atmosphere for appreciating Pisa’s architectural artistry and history without crowds. This stop lasts roughly 10 minutes, giving just enough time for a brief walk and photo opportunities.

Iconic Landmarks at Piazza del Miracoli

The Square of Miracles is the highlight of Pisa, home to the world-famous Leaning Tower, the Cathedral, and the Baptistery. Entrance to the square is free, and you can enjoy admiring these architectural marvels from outside.

While climbing the Leaning Tower and entering the Cathedral and Baptistery require tickets, which are not included, the view from the outside is enough for spectacular photos. Visitors often enjoy a classic shot “holding up” the tower and relaxing at nearby cafes with views of this UNESCO World Heritage Site. The stop lasts 30 minutes, providing ample time for sightseeing and photos.

Florence’s Panoramic View from Piazzale Michelangelo

Next, the tour takes you to Piazzale Michelangelo, positioned on a hill overlooking Florence. This viewpoint offers sweeping panoramic views of the city’s red-domed Duomo, Palazzo Vecchio, and the Arno River. A replica of Michelangelo’s David stands proudly at the center, adding to the artistic atmosphere.

Arriving by car or on foot, visitors can relax at the local café, enjoying a short 15-minute break while absorbing the stunning vistas. This stop is ideal for capturing photos and appreciating Florence from above, making it a memorable highlight of the day.

Exploring Florence’s Architectural Landmarks

The Piazza del Duomo is the city’s heart, offering a close-up view of Santa Maria del Fiore Cathedral, Brunelleschi’s Dome, Giotto’s Bell Tower, and the Baptistery of San Giovanni. The area is free to access, but tickets are needed to inside the cathedral or climb the dome and bell tower — these are not included in the tour.

Visitors can admire the frescoes by Vasari and stained glass windows inside the cathedral. The Piazza del Duomo is perfect for appreciating Florence’s Renaissance architecture and lively street life, with the entire stop lasting around 10 minutes.

The Cultural Atmosphere of Piazza della Signoria

A highlight of Florence’s historic core, Piazza della Signoria is dominated by the Palazzo Vecchio. The square is an open-air sculpture gallery, featuring Michelangelo’s replica David, Neptune’s Fountain, and a range of Renaissance statues.

The Loggia dei Lanzi displays masterpieces like Perseus with Medusa’s Head and The Rape of the Sabine Women. Surrounded by elegant cafés and historic buildings, this area offers a lively environment to soak in Florence’s artistic and political history. The stop here lasts about 1 hour, making it a perfect place to relax and enjoy the city’s atmosphere.

Crossing the Iconic Ponte Vecchio

The Ponte Vecchio is Florence’s most famous bridge, built in the 14th century. Known for its shops of high-end jewelers and goldsmiths, the bridge is a true symbol of craftsmanship and history. Walking across, visitors enjoy stunning views of the Arno River and the city skyline.

Looking up, travelers can spot the Vasari Corridor, an exclusive passageway connecting the palace to the convent. The 15-minute stop at Ponte Vecchio offers a chance to admire these architectural details and take photos of Florence’s most recognizable bridge.

Wine Tasting in Chianti’s Fattoria San Michele a Torri

The day concludes with a private wine and olive oil tasting at Fattoria San Michele a Torri, located just 15 km from Florence in the heart of Chianti. Renowned for certified organic wines and Laudemio EVO oil, this estate offers an authentic taste of Tuscany.

The guided tour of the wine cellar includes sampling three organic wines such as Chianti Classico and Chianti Colli Fiorentini. The tasting is paired with homemade bread, extra virgin olive oil, and cured meats from free-range pigs. The 1-hour experience provides insight into local wine and oil production and a chance to relax in scenic surroundings.

Practical Details: Booking and Logistics

This private tour involves round-trip transportation in a luxury vehicle, with hotel or port pickup and drop-off included. The driver/guide offers live commentary, making the day informative and enjoyable. The group size is limited to 7 people, ensuring personalized attention.

Most travelers book this tour 128 days in advance, highlighting its popularity. The total duration is approximately 9 hours, making it a full yet manageable day of sightseeing, culture, and wine tasting.

Final Thoughts on the Pisa and Florence Private Tour with Wine Tasting

This tour offers a comprehensive experience of Tuscany’s top sights, combining artistic landmarks, scenic viewpoints, and a genuine wine tasting in a private setting. The inclusion of personalized transport, expert guides, and flexible stops makes it ideal for those wanting a curated, intimate journey through Pisa and Florence.

The price of $1,299.46 covers all major activities, with no hidden fees. While lunch isn’t included, the day’s highlights and the wine tasting provide a satisfying culinary experience. The tour’s high ratings and positive reviews underscore its quality and the professionalism of guides like Enzo Dellaria and Maria Clara.

This experience suits travelers eager to cover both Pisa and Florence efficiently and those interested in Tuscan wines and oils. Its private nature and thoughtful itinerary make it a reliable choice for an enriching day exploring Italy’s artistic and gastronomic treasures.

Frequently Asked Questions

Is lunch included in this tour?
No, lunch is not included, so travelers should plan to bring or purchase their own meal during the day.

What sites are covered during the tour?
The tour includes Piazza dei Cavalieri, Leaning Tower of Pisa, Piazzale Michelangelo, Piazza del Duomo, Piazza della Signoria, and Ponte Vecchio, plus a wine tasting in the Chianti hills.

How long is the wine and olive oil tasting?
The tasting lasts approximately 1 hour at Fattoria San Michele a Torri, featuring three organic wines, bread, olive oil, and cured meats.

Are tickets to climb the Leaning Tower or inside Florence’s cathedral included?
No, tickets for climbing the Leaning Tower or entering the cathedral or baptistery are not included and need to be purchased separately if desired.

What is the group size?
The tour is private for up to 7 guests, providing an intimate experience with personalized guidance.

How far in advance should I book?
Most travelers book this tour about 128 days ahead due to its popularity and limited group size.