Pisa and Florence Private Tour with Wine Tasting

If you’re thinking about spending a day exploring Italy’s stunning cities of Pisa and Florence, this private tour promises a mix of iconic sights, cultural insights, and a delicious taste of Tuscany’s wines. Based on reviews and detailed itineraries, it’s an experience that appeals to those wanting a comprehensive, hassle-free day with personalized touches.

What we really like about this tour is its flexibility and quality of guides—your group gets a private driver and personalized commentary, which makes all the difference when you’re navigating busy sites or trying to soak in the atmosphere without the crowds. Plus, the wine tasting in Chianti is a cherry on top, giving you a true taste of the region’s flavors amid stunning scenery.

One potential downside is the price point. At around $1,300 per group (up to 7 people), this isn’t the cheapest way to see Pisa and Florence, but when you factor in private transport, guided tours, and a wine experience, it can be well worth it—especially for those who value comfort and personalized service. It’s really suited to travelers who want a seamless, all-included day without the stress of planning every detail themselves.

This tour is best for those looking for a luxury, all-in-one day trip—perfect if you prefer a personal guide, want to skip the crowds, or are celebrating a special occasion. If you’re traveling with friends, family, or a small group who appreciate comfort and insider knowledge, this could be a great fit.

Key Points

• Private, Personalized Experience: Only your group participates, ensuring a tailored day with a dedicated guide.
• Comprehensive Itinerary: Visits to Pisa, Florence highlights, and a wine tasting—packed into one day.
• Comfort & Convenience: Hotel/port pickup, luxury vehicle, and onboard WiFi make transportation smooth.
• Authentic Tuscan Flavors: Organic wine, extra virgin olive oil, and cured meats at a scenic winery.
• Flexible Booking & Expert Guides: Live commentary, knowledgeable guides, and optional additional tickets.
• Ideal for those valuing comfort and efficiency over DIY exploration.

Deep Dive into the Itinerary

Starting with Pisa’s Piazza dei Cavalieri

Your day kicks off in Pisa at Piazza dei Cavalieri, where the Renaissance architecture offers a peaceful, elegant introduction to the city’s history. It’s a quiet spot compared to the bustling Square of Miracles, and you’ll get to see Vasari’s beautiful façades, the Palazzo della Carovana, and the striking Pietro Francavilla statue of Cosimo I de Medici. While most buildings aren’t open to the public, the open-air setting allows for a leisurely stroll to admire the architecture and soak in the serene atmosphere.

One reviewer described it as a “refined gem” and appreciated the quick visit, noting it’s perfect for a brief stop to appreciate Pisa’s less crowded, more refined side. The 10-minute stop is an ideal way to set the tone for the day—an elegant introduction before heading to the more famous monuments.

Visiting the Leaning Tower and Square of Miracles

No trip to Pisa is complete without a glance at the Leaning Tower. It’s located within the UNESCO World Heritage-listed Square of Miracles, where you can admire the Tower, Cathedral, Baptistery, and Cemetery. The tour includes 30 minutes here—plenty of time for photos, a quick look inside (if you’ve purchased tickets separately), and enjoying the vibe of this iconic site.

Many visitors love capturing the classic “holding up the tower” shot, and you might want to relax at a nearby café afterward, soaking in centuries of history. During reviews, travelers appreciated the freedom to enjoy the square at their own pace, with one mentioning that the guide helped arrange Pisa climb tickets, making the experience smooth.

Scenic Drive to Florence & Overviews of the City

After Pisa, your private vehicle will take you through Tuscany’s lush countryside toward Florence. Once there, you’ll first stop at Piazzale Michelangelo, which offers breathtaking panoramic views of Florence’s skyline, from the Duomo’s red dome to the Arno River winding through the city. It’s a spot many reviews highlight as a favorite—perfect for taking in the city’s beauty and snapping some memorable photos.

From there, the tour covers Florence’s core with stops at Piazza del Duomo, Piazza della Signoria, and Ponte Vecchio. Each of these sites offers a different facet of Florence’s history and art—be it the stunning cathedral façade, the sculptures and history of Piazza della Signoria, or the centuries-old shops lining the Ponte Vecchio.

The Art and Architecture of Florence

The stops at Piazza del Duomo and Piazza della Signoria are particularly engaging for art lovers. The cathedral’s exterior, with Brunelleschi’s famous dome, is awe-inspiring, even just from the outside. Inside, you’d find impressive frescoes (not included in this tour) but the open piazza gives a great sense of Florence’s artistic grandeur.

Similarly, Palazzo Vecchio and the Loggia dei Lanzi display sculptures and masterpieces that define Florence’s Renaissance aesthetic. Visitors often mention how lively and art-rich the square feels, with many appreciating the opportunity to see these landmarks without the hassle of navigating themselves.

Cross the Ponte Vecchio & Experience the City

The Ponte Vecchio is a highlight for many. Walking across its cobblestones and browsing the jewelry shops above the river is a unique experience. With only 15 minutes here, you get a taste of Florence’s craftsmanship and history—plus stunning views of the Arno.

The Tuscan Wine Tasting Experience

The final highlight, and perhaps the most memorable part for many, is the private wine tasting at Fattoria San Michele a Torri in Chianti. Just 15 km from Florence, this organic winery offers a chance to relax and enjoy authentic Tuscan flavors.

You’ll tour the wine cellar, see how olive oil is made, and sample three premium organic wines—Chianti Classico and Chianti Colli Fiorentini—paired with freshly baked bread, extra virgin olive oil, and cured meats. Many reviewers describe the wine as excellent, with one noting it was “the best part of the trip,” appreciating the knowledgeable guide and the peaceful setting.

What Travelers Say: Authentic Insights from Reviews

Reviews give us real insights into what makes this tour special. Travelers consistently praise the guides—especially mentioning their friendliness, knowledge, and ability to manage the day smoothly even in rainy weather. One reviewer said, “Enzo was very professional and very kind,” highlighting the personal touch.

The wine tasting experience also gets glowing remarks. As one reviewer put it, “The winery experience was the best,” and the wines paired with local artisanal cured meats made the experience feel genuinely authentic. The scenic drive through Chianti’s rolling hills adds to the charm.

Others appreciated the flexibility—free to explore sights at their own pace, with some noting that the guide arranged tickets and minimized walking as needed, which is a real bonus for those wary of strenuous touring.

The Practical Side: Transportation, Cost, and Duration

This is a full-day experience, roughly 9 hours, which makes it a substantial investment of your time. The private transport in a luxury Mercedes or minivan ensures comfort, air conditioning, onboard WiFi, and a smooth ride, which is especially appreciated after long travel days or in unpredictable weather.

At about $1,300 for up to 7 people, it’s not the cheapest option, but it offers a lot of value—private guides, curated visits, wine tasting, and the convenience of door-to-door service. If you’re traveling with a small group or family who can split the cost, it becomes more reasonable.

Booking on average 128 days in advance suggests that this experience is in demand among those seeking a premium, all-inclusive day in Tuscany. The flexibility to add tickets or make restaurant reservations adds to its appeal.

Who Is This Tour Best For?

This tour suits travelers who want a stress-free, luxurious day trip with a focus on quality and comfort. It’s ideal if you love learning from local guides, want to see the key sights without crowds, and enjoy good wine. Families with older children, friends, or couples celebrating a special occasion will find it especially fitting.

However, those seeking a budget-friendly or self-guided experience might find this too costly. It’s also less suitable for those who prefer a more active, self-paced exploration without guided commentary or structured timing.

Final Thoughts

All in all, this Pisa and Florence private tour with wine tasting offers a well-rounded, comfortable way to experience two of Tuscany’s most cherished cities along with a taste of its renowned wine culture. The personalized approach, stunning vistas, and excellent guide service make it stand out, especially for those who value quality over quantity.

If you’re after a curated, hassle-free day that combines history, art, scenic views, and delicious wine, this could be just what you need. It’s best suited for travelers who appreciate a bit of luxury and are happy to invest in a memorable experience rather than DIY sightseeing.

FAQs

Is this tour suitable for children?
While the tour doesn’t specifically target families, children who enjoy sightseeing and scenic drives could find it enjoyable. Keep in mind, the tour is about 9 hours long, so it works best for older children or teenagers.

Do I need to purchase tickets separately for attractions?
Yes, tickets for climbing the Leaning Tower or entering certain sites like the Cathedral are not included. The guide can help arrange Pisa climb tickets if needed.

What’s included in the wine tasting?
You’ll sample three organic wines, including Chianti Classico and Chianti Colli Fiorentini, along with bread, extra virgin olive oil, and cured meats.

Are transportation and pickup included?
Yes, round-trip private pickup and drop-off at your hotel or port are included, along with luxury vehicle transport.

How long do we stay at each stop?
The itinerary balances sightseeing with flexibility. Typically, about 10 minutes at Piazza dei Cavalieri, 30 minutes at Pisa, 15 minutes at Piazzale Michelangelo, and about an hour in Florence’s main squares, plus 1 hour at the winery.

Can I customize the tour?
Most travelers can request additional tickets or reservations, and the guide is open to suggestions if booked in advance.

What if it rains?
The tour can still proceed, with guides adjusting the pace and possibly focusing more on indoor or sheltered sites. Rain won’t ruin the experience if you’re prepared.

Is this tour good for a romantic getaway?
Absolutely. The scenic drives, gorgeous views, and private, guided service make it a memorable and intimate way to explore Tuscany.

This tour strikes a nice balance of cultural highlights, scenic beauty, and indulgence. It’s a solid choice if you want an experience that feels curated, comfortable, and truly immersive in Tuscany’s finest offerings.