Private Day Tour from Florence to Pisa, Chianti and San Gimignano

Planning a day trip from Florence that hits all the highlights of Tuscany? This private tour offers a seamless way to explore iconic towns, stunning scenery, and indulge in local wines—all without the hassle of coordinating transport. With a dedicated driver, you’ll visit Pisa’s famous Leaning Tower, wander the medieval streets of San Gimignano, and enjoy the scenic beauty of Chianti’s vineyards, culminating in an unforgettable sunset view over Florence.

What we love most about this experience is the personalized touch—a private vehicle and driver mean flexibility and comfort, plus the opportunity to customize parts of your day. A potential drawback? The tour runs about 8 to 9 hours, so it’s a full day that requires a good energy level. This tour suits travelers who want a curated, relaxed, and culturally rich day without dealing with public transport or group tours. It’s perfect for those who adore scenic drives, delicious wines, and exploring at their own pace.

Key Points

• Private transportation offers comfort and flexibility, avoiding crowded buses and rigid schedules.
• Customizable experience allows you to enjoy Pisa, San Gimignano, Chianti, and scenic Florence views at your own pace.
• Expert drivers enhance the journey with local knowledge and tips, making the trip more enriching.
• Wine tasting option at a Tuscan farm provides a genuine taste of the region’s viticulture.
• Stunning viewpoints like Piazzale Michelangelo give a breathtaking farewell to the day.
• Value for money considering the private service, expert guidance, and multiple highlights packed into one day.

An In-Depth Look at the Tour

Hassle-Free Private Transport from Florence

Starting at 9:00 am, your private Mercedes vehicle, which reviewers praise for being spotless and comfortable, will pick you up from your hotel or designated meeting point. With a maximum group size of six, the experience balances intimacy and social ease. Having your own driver means you won’t need to worry about navigating or parking—just sit back and enjoy the scenery. Several reviews mention the driver’s attentiveness and knowledge, making the journey more engaging.

Piazzale Michelangelo: A Sunset with a View

The tour wraps up with a stop at Piazzale Michelangelo—arguably Florence’s most famous panoramic viewpoint. Just 15 minutes, but absolutely worth it, you’ll get sweeping vistas of Florence’s skyline, the Arno River, and the rolling hills beyond. As the sun sets, the sky transforms into a canvas of warm colors, making it an ideal spot for photos and reflection on your day. Reviewers often highlight this as a favorite moment, mentioning how stunning and peaceful it is after a busy day.

The Iconic Leaning Tower of Pisa

Your first major stop is Pisa’s Miracoli Square, home to the Leaning Tower, which is impossible to miss. The drive from Florence offers views of the lush Tuscan hills, setting the scene perfectly. Once there, you can explore at your own pace, soaking in the history and architecture. Tickets to climb the tower cost €12, but most visitors agree the photo-op from outside is enough to capture the moment. One reviewer notes the benefit of having a private driver who can take extra photos or answer questions while you wander.

Wine and Lunch at Farm Sant’Appiano

Next, there’s the option to visit a local farm or winery, where you can see how wine is made and taste six different varieties if you choose the €60 tasting experience. Many reviewers mention the opportunity to learn about Tuscan viticulture firsthand—something that elevates the trip beyond just sightseeing. A highlight for some was the personalized approach of the farm staff and the chance to savor local wines in a serene setting. Lunch is not included in the base price but can be added, and many find the tasting worth the extra cost for authentic regional flavors.

Exploring San Gimignano

After wine tasting, you’ll head to San Gimignano, famed for its medieval towers and charming streets. The town is compact but packed with history, local shops, and panoramic views of the surrounding countryside. Reviewer Samantha describes it as “an amazing landscape and fabulous local wines,” and many enjoy wandering its quiet streets and soaking up its timeless atmosphere. You’ll have about two hours here—enough time for photos, a quick coffee, or a stroll through artisan shops.

Scenic Drive on Chianti’s Vineyards

The journey back to Florence takes the scenic Strada Statale 222 Chiantigiana, or the Chianti wine route. Here, your driver will point out vineyards and rolling hills, often cited as one of the most beautiful drives in Tuscany. This part of the trip provides a relaxed, picture-perfect ending to your day.

The Experience and Its Value

This tour offers an impressive combination of convenience, comfort, and depth of experience. The private nature means you control the pace and focus—whether rushing through Pisa to get the perfect shot or lingering in San Gimignano’s cobbled streets. The vehicle is praised for its cleanliness and comfort, making long drives pleasant. Plus, the driver’s local knowledge often turns the journey into a mini-lesson on Tuscan culture and history.

Pricing at approximately $750 per group (up to six) might seem steep compared to group tours, but reviews consistently underline the value of having a dedicated driver and the flexibility that comes with it. This is a significant upgrade over bus tours, especially for families or small groups who can enjoy a personalized experience without sacrificing comfort.

Authentic Elements

Reviewers emphasize the authentic feel of the trip—visiting a real Tuscan farm, tasting local wines, and exploring towns that have retained their medieval charm. The optional lunch and wine tasting at Farm Sant’Appiano is a highlight, giving you not just sights but tastes of Tuscany’s viticultural heritage.

Practical Considerations

While most travelers find the timing well-balanced, keep in mind this is a packed itinerary, so early starts and full days are expected. Booking in advance is recommended, as the tour is popular and often booked 79 days ahead. Flexible pickup and drop-off make this ideal for travelers staying in Florence.

Who Would Love This Tour?

This experience is perfect for travelers who want a comprehensive, comfortable day exploring Tuscany without the stress of planning individual transport or multiple bookings. It suits those interested in history, scenic drives, and wine tasting, and who prefer personalized attention over crowded group tours. Families, couples, or small groups of friends will find this tour both enriching and relaxing.

However, if you’re looking for a very leisurely, unstructured day or have specific dietary restrictions (for lunch or wine tastings), it’s worth discussing these in advance. Those with limited mobility should also check the accessibility details of each stop.

Final Thoughts

This private tour from Florence to Pisa, Chianti, and San Gimignano offers a well-rounded day filled with iconic sights, scenic drives, and authentic Tuscan flavor. The flexibility and comfort of a private vehicle paired with knowledgeable guides make it a strong choice for those wanting an immersive experience without the hassle.

It’s especially suited for travelers who value personalized service, scenic beauty, and exceptional wine. While the price is higher than group options, many guests feel the intimacy, convenience, and quality of the experience justify the cost. If you’re after a day that balances sightseeing, relaxation, and local culture, this tour is likely to leave you with lasting memories of Tuscany’s magic.

FAQs

Is pickup included in the tour?
Yes, hotel pickup and drop-off are included, making it convenient to start your day without extra arrangements.

How long is the total tour?
The tour lasts approximately 8 to 9 hours, giving enough time to enjoy each stop without feeling rushed.

Can I customize the tour?
While the itinerary is quite structured, reviews mention that guides and drivers are attentive and open to slight adjustments, especially regarding timing or specific interests.

What is the cost of the wine tasting?
The wine tasting at Farm Sant’Appiano costs €60 per person if you choose to include it, and it features six different wines.

Are tickets to the Leaning Tower included?
No, the €12 ticket for climbing the Leaning Tower is not included and must be purchased separately if you wish to ascend.

Is lunch included in the price?
No, lunch is not included but can be added at Farm Sant’Appiano for an extra fee, which many reviews suggest is worth it for the experience.

What should I wear for this tour?
Comfortable shoes for walking around towns like San Gimignano and Pisa are recommended. Dress appropriately for the weather, especially if you plan to be outside for sunset views.

Is this tour suitable for families?
Yes, families with children or teenagers have enjoyed this experience, especially given the flexible pace and the scenic stops designed for varied interests.

This private day tour from Florence truly captures the essence of Tuscany—combining history, natural beauty, and wine, all tailored to your pace. For those seeking a personal, authentic, and memorable journey through this stunning region, it’s a choice worth considering.