Pisa and Florence Private Tour with Wine Tasting

This private day trip from Livorno combines the best of Tuscany’s architectural masterpieces, charming streets, and delicious wines—all in one seamless experience. Designed for those craving an intimate, personalized journey through Italy’s most celebrated cities, this tour offers a mix of guided sightseeing, authentic local flavor, and scenic countryside.

What we particularly love about this experience is the flexibility it offers—your private guide ensures you get a tailored visit that matches your pace and interests. Plus, the inclusion of an exclusive wine tasting in the Chianti hills adds a special touch, turning a sightseeing day into a true taste of Tuscany.

The only potential caveat? The tour covers quite a bit of ground in a short time, so if you prefer to linger longer at each site, this might feel a bit rushed. Still, if you’re after a well-rounded, authentic taste of Pisa, Florence, and the countryside, this tour hits the mark. It’s best suited for travelers who want rich cultural experiences without the hassle of planning multiple logistics.

Key Points

• Personalized Experience: Private guide and transport ensure a flexible, tailored day.
• Comprehensive Itinerary: From Pisa’s Leaning Tower to Florence’s iconic squares and a scenic wine tasting.
• Expert Guides: Knowledgeable local guides enhance your understanding and appreciation.
• Beautiful Scenery: Enjoy stunning views of Tuscany’s rolling hills and historic architecture.
• All-Inclusive Feel: Hotel/port pickup and drop-off, private transport, and wine tasting included.
• Value for Money: The price reflects the personalized service, private transport, and curated experiences.

What to Expect from Your Day in Tuscany

This tour offers a carefully curated mix of history, architecture, and local flavors, all within a manageable 9-hour window. It’s a busy day, but one designed to give you a taste of each location’s essence without feeling overwhelmed.

Starting Point: Pisa’s Piazza dei Cavalieri

Your adventure begins in Pisa’s Piazza dei Cavalieri, the city’s Renaissance political hub. Here, your guide will point out notable buildings like Vasari’s Palazzo della Carovana—home to the elite Scuola Normale Superiore—and the Palazzo dell’Orologio. These structures are stunning examples of Renaissance architecture, and the open-air setting allows for a peaceful walk among history.

The centerpiece here is Pietro Francavilla’s statue of Cosimo I de Medici, symbolizing naval strength. Around the square, the Church of Santo Stefano dei Cavalieri displays Ottoman banners and intricate interiors, but most buildings aren’t open to visitors, making this stop more about appreciating the architecture and atmosphere. Reviewers mention that the open-air setting makes it a “short but meaningful stop,” perfect for a quick photo break and a dose of historical ambiance.

The Iconic Leaning Tower of Pisa

Next, you’ll head to the Square of Miracles—home to Pisa’s most world-famous monument. While entry to the square is free, tickets are needed if you want to climb the Leaning Tower or enter the Cathedral (not included). Here, you’ll have plenty of time to admire the architecture, snap those classic photos “holding up” the tower, and take in centuries of history.

This stop typically lasts around 30 minutes, giving you enough time to soak in the scene, grab coffee at a nearby café, and reflect on how this tower’s tilt has defied expectations for over 800 years. Reviewers appreciate that the tour includes this stop, and many comment on how the architecture is even more impressive in person.

Scenic Drive to Florence with Panoramic Views

The drive from Pisa to Florence offers a glimpse into the Tuscan landscape—picturesque hills, vineyards, and rolling farmland. Your private guide will likely share insights about the region’s history and wine traditions, adding context to your later tasting.

Florence’s Top Sights, Step-by-Step

Once in Florence, the itinerary hits all the high notes, starting with Piazzale Michelangelo. This viewpoint, perched on a hill just outside the city center, provides one of the most breathtaking panoramic vistas of Florence. You’ll see the Duomo’s red dome, Palazzo Vecchio’s towers, and the flowing Arno River. Many reviewers praise this stop for its “unforgettable views,” and it’s a perfect spot for a quick espresso or just to soak in the city below.

Next is the Piazza del Duomo, where the grandeur of Florence’s cathedral, Brunelleschi’s Dome, and Giotto’s Bell Tower come into view. While the interior isn’t included, you’ll get a close-up look at the stunning façade and the impressive architecture that defines Florence. This square is a must-see for art and architecture lovers, with many noting how the outside alone offers enough awe-inspiring beauty.

Piazza della Signoria and Ponte Vecchio

The tour continues through Florence’s historic heart—Piazza della Signoria. Here, you’ll see the replica of Michelangelo’s David, Neptune’s Fountain, and the Loggia dei Lanzi. The square pulses with Renaissance history, and many reviews highlight how this bustling space is perfect for people-watching and soaking in Florence’s artistic vibe.

Walking over the Ponte Vecchio, the most famous bridge in Florence, offers a chance to appreciate centuries of craftsmanship. The row of jewelers and goldsmith shops on the bridge is a living testament to Florence’s artisanal tradition. Reviewers mention the Vasari Corridor above the shops as a fascinating hidden detail, adding an extra layer of history to this picturesque crossing.

Authentic Tuscany Wine Tasting

About 15 km from Florence, in the heart of Chianti, you’ll visit Fattoria San Michele a Torri. This private estate, known for organic wines and Laudemio EVO oil, provides an authentic taste of the region’s culinary craftsmanship. The guided tour of the wine cellar, paired with a tasting of three premium organic wines—including Chianti Classico—makes for a memorable experience.

You’ll also enjoy homemade bread, artisanal cured meats, and the estate’s award-winning extra virgin olive oil. Reviewers rave about the guides’ knowledge and the quality of the wines, noting that this part of the tour elevates the entire day into a true “wine lover’s dream.” The setting in the Chianti hills adds a peaceful, scenic backdrop to this tasting.

Comfortable, Private Transportation

One of the highlights of this tour is the private Mercedes vehicle—luxuriously appointed, air-conditioned, and equipped with WiFi. This means your group can relax between sightseeing stops, avoiding the stress and fatigue of crowded group tours. The driver/guide provides live commentary, enhancing your understanding of each site and its history.

Practical Details and Value

This tour costs $1,299.46 for up to 7 people, which, when split among a group, offers good value considering the private transport, guided visits, and wine tasting included. It’s a comprehensive package that covers transportation, expert guiding, and authentic experiences, making it a convenient way to explore Tuscany without the stress of planning each detail yourself.

Guests consistently mention the professionalism of the guides—names like Enzo, Maria Clara, and Carlos come up frequently—and how their knowledge and friendly demeanor make the experience memorable. The tour’s 128 days in advance booking rate reflects its popularity, and reviews confirm that it’s well organized and punctual.

Who Is This Tour Best For?

This experience suits travelers who value personalized service, want to see both Pisa and Florence in one day, and have an appreciation for good wine and authentic local experiences. It’s ideal for small groups or families who prefer a relaxed, guided approach rather than rushing independently. It also appeals to those who enjoy scenic drives and stunning vistas, as well as anyone eager to learn about Tuscany’s wine heritage without the hassle of self-organizing.

The Sum Up

For anyone looking to maximize a day in Tuscany with a mix of culture, history, and flavor, this private tour offers outstanding value. The combination of expert guides, scenic drives, and authentic wine tasting makes it a well-rounded experience that captures the essence of the region.

The tour’s carefully curated stops mean you’ll walk away with a solid understanding of Pisa’s architectural marvels, Florence’s artistic treasures, and the chance to indulge in some of Italy’s finest wines. Its private nature ensures a relaxed, tailored experience—perfect for those who prefer to explore with a bit of insider knowledge and VIP treatment.

While it’s a full day, that’s part of the appeal for many—covering a lot of ground in comfort, with the freedom to customize slightly if needed. For travelers seeking a memorable, hassle-free way to enjoy Tuscany’s highlights, this tour hits the sweet spot.

FAQ

Is this tour suitable for small children?
Yes, the private nature and flexible schedule make it suitable for families. Just be mindful of the walking involved, especially at sites like Piazzale Michelangelo and Ponte Vecchio.

What is included in the price?
The cost covers private round-trip transport, hotel or port pickup and drop-off, a driver/guide, live commentary, and the wine tasting experience in Chianti. Lunch and tickets for interior visits are not included.

Can I purchase tickets for the attractions?
Yes, if you wish to access sites like the cathedral or climb the Leaning Tower, you can buy tickets separately during the tour, or ask your guide to help arrange them.

How long is the drive between sites?
The drive from Pisa to Florence is scenic and typically smooth, with stops along the way for comfort and sightseeing. The total touring time is approximately 9 hours, including stops.

Is there any optional activity or upgrade available?
While the tour includes the main sites and wine tasting, you can request additional tickets or restaurant reservations if needed, subject to prior arrangement.

What should I wear?
Comfortable shoes are recommended since there’s some walking involved, especially at Florence’s piazzas and Pisa’s square. Weather-appropriate clothing is advised, and don’t forget sun protection or an umbrella depending on the forecast.

This private tour offers a genuine taste of Tuscany’s beauty, history, and flavors, all wrapped up in a personalized, stress-free package. Whether you’re a history buff, a wine lover, or simply eager to soak up Italy’s best sights without the crowds, it’s a day that promises to leave lasting memories.