Private day trip to Siena, San Gimignano, Chianti and Pisa, from Florence

Make the most of a full 10-hour private journey through Tuscany with this expertly curated day trip from Florence. For $444.09 per person, you gain exclusive access to Siena, San Gimignano, and Pisa, all with the comfort of private transportation in a Mercedes vehicle equipped with air conditioning and onboard Wi-Fi. The tour is highly rated, with a perfect 5.0 based on 80 reviews, and is recommended by 99% of participants. Designed for flexibility, it offers a personalized itinerary, pickup from anywhere in Florence, and the chance to explore at your own pace—whether you want sightseeing, shopping, or simply soaking in the scenery.

This tour suits travelers who appreciate a private, customizable experience with knowledgeable drivers, and who value comfort and convenience. It’s an ideal choice for those wanting to see multiple highlights in one day without the stress of organizing logistics or group tours. Be aware that lunch and entrance fees are not included, giving you the freedom to choose whether to enjoy a casual meal or visit a specific site on your own.

Key Points

• Private, fully customizable day trip from Florence to Siena, San Gimignano, and Pisa
• Duration of approximately 10 hours, with flexible timing for each stop
• Includes private Mercedes transportation with air conditioning and Wi-Fi
• Hassle-free pickup and drop-off anywhere in Florence
• Visit iconic sites like Piazza del Campo, San Gimignano’s medieval towers, and the Leaning Tower of Pisa
• Tour guides are not included, but the driver provides detailed explanations and local tips

Starting the Day with Private Pickup in Florence

The tour begins with a pickup at your accommodation or preferred location in Florence. Your private driver, who speaks English fluently, will greet you and provide a brief overview of the day. The vehicle is a luxurious Mercedes with air conditioning and Wi-Fi, ensuring a comfortable ride throughout the approximately 1-hour drive to Siena. This personalized start means you avoid crowded buses and set your own pace from the beginning.

Scenic Drive through Tuscan Countryside

As the journey to Siena commences, the driver shares insights about the rolling hills, vineyards, and olive groves that characterize the Tuscan landscape. The ride is about one hour, offering plenty of opportunity to enjoy the views and prepare for the sightseeing ahead. The driver’s friendly approach and informative commentary make the trip engaging, setting a relaxed tone for the day.

Exploring Siena’s Medieval Charm

Upon arriving in Siena, the focus shifts to one of Tuscany’s most beautiful cities. Two hours are allocated to explore Siena’s narrow streets, medieval towers, and charming squares. The highlight is the famous Piazza del Campo, where the Palio horserace takes place twice yearly. The Gothic cathedral—one of the most important in the region—is also a key attraction, offering impressive architecture and art. Visitors can browse local shops, ideal for those interested in ceramics, leather goods, and souvenirs, all without the need for a guided tour.

San Gimignano’s Tower Skyline and Tasting Options

The drive from Siena to San Gimignano takes roughly 45 minutes. Once there, travelers are free to admire the distinctive skyline made up of 13 medieval towers, which earn the town its nickname as the “Medieval Manhattan.” Visitors can walk through the historic streets, visit the Duomo or Collegiata Church, and explore the Palazzo Nuovo del Podestà, now serving as the town hall. While lunch and wine tasting are on your own, the driver can suggest local options—whether a sit-down meal at a countryside restaurant or a quick snack with a glass of famous Chianti red wine.

Shopping and Local Products in San Gimignano

San Gimignano offers plenty of opportunities for shopping enthusiasts. Specialty shops sell ceramics, leather goods, linens, and regional products such as Vernaccia white wine. The Museum of Torture is also available for those interested in a more unusual historical experience. With about 1 hour and 30 minutes at this stop, you have ample time to shop, sightsee, or enjoy a casual coffee or gelato.

Pisa’s Leaning Tower and Iconic Piazza

The journey continues with a drop-off at Piazza dei Miracoli in Pisa, famed for the Leaning Tower of Pisa. You receive one hour to marvel at the architectural complex, which includes the cathedral, baptistery, and Campo Santo cemetery. While climbing the tower requires an entrance fee, the opportunity to walk around and admire the world-renowned Leaning Tower and surrounding monuments makes this stop a memorable highlight.

Ending with a Relaxing Drive Back to Florence

After a full day of sightseeing, your driver will escort you on a one-hour drive back to Florence. This is the perfect time to relax, reflect on the day’s adventures, and enjoy the scenic Tuscan landscape one last time. The transfer back is straightforward, leaving you free to plan the rest of your evening in Florence.

Logistics and Practical Details

The tour is entirely private, meaning only your group participates, and the driver can adapt the schedule to fit your interests and pace. The mobile ticket offers convenience, and the group discount options make it an attractive choice for families or small groups. The tour costs $444.09 per person, with all fees and taxes included, but lunch and entrance fees are not covered—allowing flexibility for your preferred dining and sightseeing choices.

The Experience in Review: Highlights From Feedback

While specific reviews focus mainly on driver excellence and personalized service, it’s clear that knowledgeable guides like Alessio, Giuseppe, Donatello, Mario, and Paolo enhance the experience through their friendly demeanor and local insights. Travelers consistently praise the comfortable vehicle, flexible timing, and beautiful scenery. Many mention how the driver’s suggestions for lunch or local stops add a personalized touch, making this tour feel more like a bespoke journey than a cookie-cutter group outing.

Who Will Love This Tour?

This private day trip is perfect for those seeking comfort and flexibility. It appeals strongly to families, couples, or small groups who want a personalized experience, with the freedom to customize their stops. The luxury vehicle and private driver also make it suitable for travelers with mobility concerns or those who value a relaxed, stress-free day.

Final Thoughts on the Tuscany Private Day Trip

This tour offers excellent value and convenience. The private Mercedes transportation, combined with customizable stops at Siena, San Gimignano, and Pisa, provides a smooth, enjoyable way to see some of Tuscany’s most iconic sites. The high praise for drivers’ knowledge and friendliness makes it stand out from standard group tours.

While you need to arrange your own lunch and pay entrance fees if desired, the flexibility allows for a personalized experience tailored to your preferences. This tour is best suited for travelers who appreciate comfort, independence, and expert local insights. It delivers a well-rounded day of sightseeing, scenic drives, and memorable sights in one of Italy’s most enchanting regions.

Frequently Asked Questions

Is this tour suitable for families with children?
Yes, the private nature and flexible schedule make it a good choice for families, especially with children who may need a more relaxed pace.

Can I choose where to stop for lunch?
Lunch is on your own, and the driver can suggest local restaurants or quick options, giving you the chance to select your preferred dining style.

Are entrance fees to sites included?
No, entrance fees are not included, so you can decide whether to visit attractions like the Pisa Tower or Siena Cathedral at your own expense.

How long is the drive between each stop?
The drive from Florence to Siena takes about 1 hour, from Siena to San Gimignano approximately 45 minutes, and from San Gimignano to Pisa roughly 1 hour. The return trip also lasts about 1 hour.

What makes this tour stand out?
The personalized itinerary, luxury Mercedes vehicle, and highly rated drivers are key advantages that set this tour apart from standard group options.

Is there a group size limit?
This is a private tour, so only your group participates, ensuring a more intimate experience.

Can I customize the time spent at each site?
Yes, the driver provides a briefing to tailor the schedule according to your interests and needs.

Is the tour accessible for travelers with mobility issues?
While specific accessibility details aren’t provided, the private vehicle and flexible schedule generally accommodate various needs better than larger group tours.

What do reviews highlight most about this tour?
Travelers frequently praise the driver’s knowledge, friendliness, and ability to customize the experience, along with the comfort of the vehicle and scenic drives.

How do I book this tour?
You can reserve via the provided booking platform, with free cancellation up to 24 hours in advance, making it easy to plan with confidence.