Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence

Exploring Tuscany in a single day becomes effortlessly enjoyable with the Private Tuscany Tour from Florence, offered at $673.42 per person. This tour spans approximately 10 hours and combines the charm of three iconic cities—Siena, Pisa, and San Gimignano—with the comfort of a private Mercedes vehicle, complete with hotel pickup and drop-off. With a strong average rating of 5.0 from 134 reviews and 95% recommendation rate, this experience appeals to travelers seeking a luxury, flexible, and personalized way to see Tuscany’s highlights.

A key feature of this tour is the self-guided exploration at each stop, giving visitors the freedom to linger or move quickly through the cities. The driver/guide is available for customized stops and local tips, but it’s important to remember that this is only a private driver service—additional tickets and activities like Pisa’s Tower or Siena Cathedral cost extra. This tour is especially suitable for those who value comfort, flexibility, and a curated experience over a strictly guided group tour.

Key Points

• Private driver service with luxury Mercedes vehicle offering free Wi-Fi and USB chargers
• Flexible schedule with free time in Siena, San Gimignano, and Pisa, including lunch at a winery
• Approximate 10-hour tour starting from Florence hotel pickup at 8:30 am
• Includes stops at Piazza del Campo, San Gimignano’s towers, and Piazza dei Miracoli with the Leaning Tower of Pisa
• Additional costs apply for entry tickets like Pisa Tower (~$20) or Siena Cathedral (~$10)
• Highly praised for knowledgeable drivers and customizable experience
• Not a guided tour—you get a driver, but tickets and inside visits are separate

Pickup from Florence and Scenic Drive into Tuscany

The tour begins with a hotel pickup in Florence around 8:30 am in a fully-fitted Mercedes vehicle. The drive out of Florence offers a beautiful view of Tuscany’s rolling hills, vineyards, and picturesque towns, setting a relaxed tone for the day.

This private transfer allows for custom stops along the way, depending on your preferences. The luxury vehicle includes free Wi-Fi, air conditioning, and USB ports, making the journey comfortable even on the warmest days.

Exploring Siena’s UNESCO World Heritage Old Town

Arriving in Siena, you get close access to the Siena Cathedral, with self-guided exploration planned for about two hours. This medieval city is famous for its shell-shaped Piazza del Campo, which hosts the Palio horse race every summer.

Within the historical center, you’ll find art galleries, artisanal shops, and award-winning restaurants. The Torre del Mangia, a spectacular clock tower that is the third tallest in Italy, offers panoramic views of the city’s rooftops and the surrounding countryside. While climbing the tower incurs an extra fee, the exterior views alone make it worth noting.

The Siena Cathedral features a breathtaking facade with colored marbles and Romanesque-Gothic architecture. Inside, you’ll see marble mosaics, Renaissance artworks, and the Piccolomini Library—a highlight of the visit. Entrance tickets are not included, so plan accordingly if you wish to go inside.

San Gimignano’s Medieval Skyline and Tower Views

After a relaxing drive through the Tuscan countryside, the tour reaches San Gimignano, a hilltop town renowned for its 13 medieval towers resembling a medieval Manhattan. The driver drops visitors outside the ancient gate, and you are free to spend about an hour wandering and admiring the well-preserved architecture.

The Collegiata of Santa Maria Assunta, a famous church, is among the points of interest, with colorful frescoes inside. For breathtaking views of the countryside, a panoramic viewpoint is available, offering perfect photo opportunities.

In the main square, Piazza della Cisterna, visitors can enjoy gelato or coffee, soaking in the lively medieval atmosphere. Entrance to the Collegiata or Museums might be optional, with tickets not included in the tour price.

Tasting Tuscany’s Wines at a Hilltop Winery

One of the most praised features of this tour is the lunch at a private winery. The driver can arrange stops at vineyards where visitors enjoy wine tastings and a multi-course meal featuring local Tuscan dishes.

This unexpected highlight is often described as spectacular, with some describing it as a lifetime memory. The lunch typically includes local wines like Vernaccia, and the setting on a hilltop enhances the experience. This stop is highly recommended by guests for its authenticity and quality.

Pisa’s Piazza dei Miracoli and the Leaning Tower

After lunch, the trip continues to Pisa, about an hour’s drive from San Gimignano. The focus here is on the Piazza dei Miracoli, home to white marble monuments including the Leaning Tower and the cathedral.

Visitors can snap photos in front of the Leaning Tower and inside if they choose, although tower tickets (~$20) are not included. Climbing to the top offers detailed views of Pisa’s rooftops and the surrounding city.

The cathedral is a notable example of Pisan Romanesque architecture with intricate carvings and famous artworks like Cimabue’s frescoes and Giovanni Pisano’s pulpit. Entry is free, but some interior attractions may require an additional ticket.

Return to Florence in Comfort and Style

Following the Pisa visit, the driver takes travelers back to Florence in a comfortable, private Mercedes vehicle. The return journey lasts around one hour, providing time to relax and reflect on the day’s sights.

The tour concludes with hotel drop-off in Florence, leaving guests with memories of a well-curated day in Tuscany, blending cultural highlights, scenic views, and culinary delights.

Who Will Appreciate This Tour Most?

This private day trip suits those who prefer flexibility and want to avoid crowded group tours. The self-guided stops enable personalized pacing, especially if some sites interest more than others. The lunch at the winery is a favorite, offering a taste of Tuscany beyond the typical sightseeing.

However, it’s important to remember that entry tickets at sites like Pisa Tower and Siena Cathedral are not included, so budget for those if inside visits are desired. Also, the driver is not a guide—while many guests praise their driver, some note that not all drivers are equally knowledgeable about the sites.

Why This Tour Offers Good Value

For $673.42, this tour provides a luxurious vehicle, hotel pickup and drop-off, and significant free time in three major cities. Guests consistently highlight friendly, knowledgeable drivers who customize stops and make the experience relaxing and enjoyable.

Guests also appreciate the ability to choose how long to stay at each location and the opportunity to combine sightseeing with a fabulous Tuscan winery lunch. Although tickets and additional activities are extra, the overall flexibility and comfort make this a strong option for travelers seeking a personalized, stress-free day in Tuscany.

Frequently Asked Questions

Is this tour guided or just transportation?
This is only a private driver service; additional tickets and inside visits like Pisa Tower or Siena Cathedral are not included.

Can I customize my stops?
Yes, the driver is available for customized stops and free time in each city, based on your preferences.

How long is the drive between cities?
The drive from Florence to Siena takes about one hour, San Gimignano is on the route, and Pisa is about another one hour from San Gimignano.

Are lunch and tickets included?
No, lunch at a winery is arranged but additional costs apply, and site entry tickets are extra.

What should I bring for the day?
Comfortable shoes for walking, cash or cards for additional tickets, and camera gear for photos.

Is this tour suitable for children?
Yes, the tour is flexible, and the vehicle is large and comfortable, making it suitable for families, especially with arrangements for free time.

How do I book this tour?
Booking can be made in advance, with most reservations 31 days or more ahead, and full cancellation is available up to 24 hours before the start.

What makes this tour stand out compared to group tours?
The personalized experience, luxury transport, and ability to tailor stops make it an attractive choice for travelers seeking comfort and flexibility in Tuscany.

This Private Tuscany Tour from Florence offers a well-rounded, comfortable way to see three iconic cities in one day, with the added bonus of a wine luncheon and flexible schedule. It’s perfect for those valuing luxury, independence, and authentic experiences in Italy’s beautiful countryside.