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

Traveling through Italy’s countryside is one of those experiences that stays with you long after the trip ends. If you’re short on time but want to soak up the essence of Tuscany, a private day tour from Florence to Pisa, Chianti, and San Gimignano might be just what you need. Based on the rave reviews and detailed itineraries, this tour promises a mix of iconic sights, breathtaking landscapes, and a taste of local wine and charm—all with the convenience of private transportation.

What we really like about this experience is the personalized touch—you’re not stuck in a big bus with strangers, but instead with your own driver and guide, allowing for flexibility and comfort. Plus, the stunning sunset view from Piazzale Michelangelo gives an extra magical finish to your day. A small but noteworthy point: if you’re not keen on spending extra for wine tastings or entrance fees, some parts of this tour might be less appealing, but overall, it offers excellent value considering the inclusions and flexibility.

This tour is ideal for travelers who appreciate comfort, tailor-made experiences, and the chance to see multiple highlights in one day. It’s perfect if you want to avoid the hassle of navigating public transport or booking multiple tickets, and it suits those who enjoy scenic drives, cultural exploration, and relaxed sightseeing.

Key Points

• Private transportation ensures comfort and flexibility throughout the day.
• Scenic stops like Piazzale Michelangelo offer unforgettable views of Florence at sunset.
• Iconic sights include the Leaning Tower of Pisa and San Gimignano’s medieval charm.
• Wine tasting options at a Tuscan farm add a flavorful local touch, with the possibility for an included lunch.
• Customizable experience with knowledgeable guides and drivers who can adapt parts of the tour.
• Cost reflects exclusivity—it’s more expensive than group tours but offers a personalized, relaxed experience.

What to Expect on the Tour

This private day trip is designed to give you a comprehensive taste of Tuscany’s most famous sights, paired with scenic drives and cultural insights. Starting at 9:00 am, your driver will pick you up from your Florence hotel in a sleek Mercedes-Benz vehicle, ensuring a comfortable ride from the outset. The day is generally around 8 to 9 hours long, allowing ample time at each stop without feeling rushed.

First stop: Piazzale Michelangelo

Your day begins with a stop at Piazzale Michelangelo, one of Florence’s most iconic viewpoints. Here, you can snap photos of the city’s skyline, Arno River, and surrounding hills, especially as the sky turns golden at sunset. Expect about 15 minutes to soak in the views, which are simply stunning and well worth the early start.

Next: Pisa and the Leaning Tower

From Florence, your private driver will take you to Pisa, weaving through the rolling Tuscan landscape. Once in Pisa, you’ll head straight to the Miracoli Square to see the Leaning Tower of Pisa—the star of millions of photos for a reason. While the tour doesn’t include entry tickets (which cost €12), you’re free to explore the area at your own pace. The reviews praise the flexibility here; you can take your time, capture that perfect shot, or just enjoy soaking in the historic ambiance.

Third stop: Farm Sant’Appiano and Wine Tasting

Midday, you’ll visit a local Tuscan farm, where you have the option for a wine tasting experience. For €60 per person, you can enjoy a delicious lunch paired with six different wines, learning about the wine production process firsthand. Even if you decide not to partake in the tasting, the farm offers a scenic break from sightseeing and a chance to step into genuine Tuscan life.

Afternoon: San Gimignano

Later, your journey takes you to San Gimignano, renowned for its medieval towers and charming narrow streets. It’s a perfect spot to wander, admire panoramic views of the countryside, and soak up the historic atmosphere. You’ll have around two hours here, enough to explore at leisure and maybe grab a gelato or some local souvenirs.

Scenic Return: Chianti Wine Route

On your way back to Florence, you’ll enjoy the Chiantigiana road—known for its breathtaking vineyards and rolling hills. This part of the trip offers some of the most picturesque vistas in Tuscany, perfect for photo ops and simply relaxing as your driver navigates the scenic route.

The Experience of the Guides and Vehicles

The reviews highlight the knowledgeable and personable guides, notably Francesco and Luigi, who go beyond just driving—they share insights and even customize parts of the tour based on your interests. The vehicle is described as clean, comfortable, and equipped with amenities like bottled water, ensuring a pleasant journey.

Flexibility and Convenience

One of the biggest advantages of choosing this private tour is the flexibility. You’re not bound by fixed group schedules or crowded buses. Instead, your driver can adapt the stops, timing, or even suggest additional viewpoints if you ask. This flexibility is especially valued by travelers who appreciate a more personalized experience.

Is It Worth the Price?

At $754.70 for a group of up to six people, this tour isn’t cheap. But considering the personalized service, private transport, and the variety of stops packed into a single day, many travelers find it offers excellent value. The reviews suggest that the guide’s knowledge and the comfort of the vehicle significantly enhance the experience, making it feel like a luxury day out rather than just a sightseeing trip.

It’s also worth noting that the tour includes hotel pickup and drop-off—something that saves you time and hassle, especially if you’re staying outside the city center. The bottled water and the option for a wine tasting or lunch add further value, allowing you to indulge without worrying about extra costs.

Who Should Consider This Tour?

This private tour is best suited for those who:

• Want a stress-free day exploring Tuscany’s highlights.
• Prefer personalized service over bus tours.
• Are interested in wine tasting and authentic local experiences.
• Have a flexible schedule and appreciate scenic drives.
• Are traveling in a small group or as a couple seeking intimacy and comfort.

If you’re traveling with family or friends who enjoy a relaxed pace, this trip can easily accommodate your needs. However, if your priority is budget or you prefer a more structured group experience, you might look elsewhere.

This private day tour from Florence to Pisa, Chianti, and San Gimignano offers a well-rounded, enjoyable way to see some of Tuscany’s most famous sights with minimal hassle. The flexibility, personal touch, and scenic beauty make it a standout for those seeking comfort and authenticity in their Tuscan adventure. Expect a full package—stunning views, informative guides, and delicious wine—crafted to make your day memorable.

If you’re after a tailored experience that balances sightseeing with relaxation, this tour could be just the ticket. It’s particularly suited for travelers who value quality over quantity and want to enjoy Tuscany at their own pace, all while being pampered by knowledgeable guides and comfortable transport.

How early does the tour start?
The tour begins at 9:00 am, with pickup from your Florence hotel.

What is included in the price?
The price covers private transportation in a Mercedes-Benz vehicle, hotel pickup and drop-off, bottled water, and the flexibility to enjoy the stops at your own pace.

Are entry tickets to the Leaning Tower of Pisa included?
No, tickets (€12) are not included, giving you the freedom to visit if you choose and at your own convenience.

Can I customize the tour?
Yes, guides like Luigi and Francesco have been noted for their ability to customize and communicate in advance to tailor the experience.

Is lunch included?
Lunch is optional at Farm Sant’Appiano for €60 per person, which includes a tasting of six wines and a meal.

How much time is spent at each stop?
Most stops allow around 2 hours—enough for sightseeing, photos, and short explorations, with the sunset view at Piazzale Michelangelo being a highlight.

Is this tour suitable for families?
While not specifically marketed as family-oriented, the small group size and private transport make it comfortable for travelers of all ages, provided children are comfortable with sightseeing and driving.

How scenic is the drive?
The drive through Chianti and the countryside is frequently praised for its breathtaking views of vineyards and rolling hills.

How long is the overall tour?
Expect around 8 to 9 hours, including traveling, stops, and some free time in each location.

What should I wear?
Comfortable clothing and shoes are recommended, especially for walking around towns and vineyards.

If you’re ready for a day that combines culture, scenery, and excellent wine—all in a relaxed, private setting—this Tuscany tour could be just what you need.