Setting out on a private day trip from Florence, visitors can enjoy the medieval charm and stunning landscapes of Tuscany. This comprehensive tour takes them to the historic cities of Siena, San Gimignano, and Pisa, offering a chance to explore their iconic landmarks, savor local wines, and bask in the picturesque Chianti region. With a customizable itinerary and comfortable transportation, this excursion promises a well-rounded experience of Tuscany’s rich cultural heritage.
Key Points

- Comprehensive private day trip exploring historic Tuscan cities of Siena, San Gimignano, Chianti, and Pisa, with a highly flexible and customizable itinerary.
- Scenic journey along the Chianti road, with visits to iconic landmarks like Siena’s Piazza del Campo, Gothic cathedral, and the Leaning Tower of Pisa.
- Personalized pre-trip briefing with the driver to create a schedule tailored to individual interests, allowing ample time for sightseeing, shopping, and dining.
- Comfortable private transportation in a Mercedes vehicle equipped with air-conditioning and Wi-Fi, ensuring a smooth and efficient journey.
- Guided exploration of Siena’s medieval architecture and rich cultural heritage, as well as the UNESCO World Heritage site of Pisa’s Leaning Tower.
Overview of the Tour

This private day trip offers visitors a chance to explore the historic cities of Siena, San Gimignano, Chianti, and Pisa from Florence.
With a 5.0 rating and 98% recommendation from 64 reviews, the tour provides a comprehensive experience.
Travelers will journey along the scenic Chianti road, visit Siena’s Piazza del Campo and Gothic cathedral, enjoy lunch and wine tasting in San Gimignano, and see the iconic Leaning Tower of Pisa.
The flexible itinerary allows for customization based on individual interests, ensuring a personalized day of sightseeing, shopping, and dining at local restaurants.
Here are more experiences we've reviewed in Florence
Itinerary and Customization
How flexible is the itinerary for this private day trip?
The itinerary is highly flexible, allowing travelers to tailor the day to their individual interests. Before setting off, travelers meet with the driver for a briefing to build a personalized schedule.
This ensures ample time is allocated for sightseeing, shopping, and dining at local restaurants in Siena, San Gimignano, and Pisa. The driver is knowledgeable and eager to accommodate any requests, making this a truly customized experience.
With this flexibility, travelers can maximize their time and fully enjoy the charm of Tuscany.
Transportation and Amenities

For this private day trip, travelers are provided with private transportation in a comfortable Mercedes vehicle equipped with air-conditioning and Wi-Fi.
Hassle-free pickup and drop-off from any location in Florence is included. Bottled water, all fees and taxes, and lunch (at travelers’ own expense) are also provided.
The transportation offers a smooth and efficient way to navigate the trip, allowing travelers to focus on the sights and experiences.
With these amenities, the tour ensures a comfortable and convenient journey throughout the day.
Exploring Siena

As the tour ventures towards Siena, travelers are captivated by the city’s striking medieval architecture and rich cultural heritage.
The tour explores the iconic Piazza del Campo, a unique shell-shaped plaza that serves as the heart of Siena. Visitors marvel at the Gothic grandeur of the Siena Cathedral, known for its intricate marble facade and stunning interiors.
The driver provides insightful commentary, guiding guests through the winding streets and sharing the fascinating history of Siena’s rise as a powerful medieval city-state.
This stop offers a glimpse into Tuscany’s remarkable past and the enduring allure of its historic towns.
Discovering San Gimignano

The tour then takes visitors to the captivating hilltop town of San Gimignano. Known as the "Medieval Manhattan" for its iconic skyline of 14 towering medieval stone towers, this Tuscan gem offers a step back in time.
Guests will have time to explore the charming squares, browse local shops, and enjoy a traditional Tuscan lunch paired with a wine tasting. The town’s well-preserved architecture, picturesque landscapes, and authentic cuisine make it a highlight of the day trip.
After savoring the local flavors, the tour continues to the famous Leaning Tower of Pisa.
Prefer keeping things personal? Here are more private experiences we've reviewed in Florence
- Florence Private Tour With a Local – Highlights & Hidden Gems
- Cinque Terre and Pisa Tower Tour From Florence Semi Private
- Private Day Trip Tuscany Landscape and Wine Tasting From Florence
- PALAZZO VECCHIO Private Tour in Florence
- Private Full Day Walking Tour of Florence Highlights With Uffizi and Accademia
- Private Photo Tour in Florence With a Professional Photographer
Experiencing the Chianti Region

After exploring the medieval charm of Siena, the tour winds its way through the picturesque Chianti region.
Travelers journey along the Chianti road, taking in the rolling hills, vineyards, and charming villages that define this renowned winemaking area.
The group stops for a wine tasting and lunch at a local winery in San Gimignano, savoring the region’s renowned Chianti wines and delectable cuisine.
With ample time allocated, guests can wander the quaint streets, browse the shops, and soak up the unique atmosphere of this historic destination before continuing on to the iconic Leaning Tower of Pisa.
Visiting the Leaning Tower of Pisa

Leaving the rolling vineyards and medieval towers of Siena and San Gimignano behind, the tour culminates with a visit to the iconic Leaning Tower of Pisa.
The driver will transport guests directly to the historic Piazza dei Miracoli, home to the renowned marble tower. Visitors can admire the architectural marvel, take photos, and explore the surrounding area.
Optional activities include climbing the 293 steps to the top of the tower or visiting the adjacent Pisa Cathedral and Baptistery.
With ample time allocated, guests can soak in the history and unique ambiance of this world-famous UNESCO World Heritage site.
Customer Feedback and Recommendations

Travelers consistently praise the private day trip for its exceptional customer service and personalized experiences.
With a 5.0 rating from 64 reviews, the tour earns a 98% recommendation from previous participants.
Highlights include the knowledgeable, friendly drivers – such as Alessio, Donatello, Mario, and Paolo – who provide informative and engaging guidance throughout the journey.
Clients appreciate the flexibility to customize the itinerary to suit their interests, allowing ample time for sightseeing, shopping, and dining.
The comfortable Mercedes vehicle, complimentary bottled water, and hassle-free pickup and drop-off in Florence further contribute to the tour’s positive reputation among travelers.
Frequently Asked Questions
What Time Does the Tour Start and End?
The tour start and end times are not explicitly stated in the overview. The itinerary is flexible, allowing the driver to build a personalized day based on individual interests and schedules.
How Many People Can Be Accommodated in the Private Vehicle?
The private vehicle can accommodate up to a maximum of 8 passengers. The size of the Mercedes vehicle provides comfortable transportation for small groups to visit the various destinations covered during the tour.
Are There Any Special Dietary Requirements That Can Be Accommodated?
The tour can accommodate dietary needs such as vegetarian, vegan, or gluten-free. Travelers should notify the provider in advance to ensure appropriate arrangements are made for lunch and any other food-related activities.
Can the Tour Be Booked for a Different Day Than the One Listed?
Yes, the tour can be booked for a different day than the one listed. The itinerary is flexible, allowing the driver to customize the day to suit individual interests and schedules.
Is There an Option to Extend the Tour to Include Additional Destinations?
The tour allows for a flexible itinerary, so travelers can extend the day trip to include additional destinations they’re interested in. The driver will work with guests to build a personalized schedule that suits their preferences.
The Sum Up
This private day trip from Florence offers a wonderful opportunity to take in the rich history and picturesque landscapes of Tuscany. Visitors can explore the medieval charm of Siena, indulge in wine tasting in San Gimignano, and marvel at the iconic Leaning Tower of Pisa, all while enjoying the scenic journey through the Chianti region. It’s a comprehensive and customizable experience that allows travelers to fully appreciate the essence of this enchanting part of Italy.
More Historical Tours in Florence
- Florence Medici Bike Tour Cycle Through History and Power
- Florence Wine &Food: Taste Tuscan Flavors in Historic Cellar
- Florence: Guided visit of architecture and history
- Guided Medici Tour Florence: Discover Mysteries & History
- The History of Florence: The Renaissance Era Private Tour
- Florence Tour: Michelangelo’s David and Historic Center
More Tour Reviews in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Fiesole E-Bike Tour with Olive Oil Tasting or Pool & Chill
- Florence: Tuscan Cheese and Wine Tasting Experience
- Florence walking Tour: Music Headphones & Aperol Spritz
- Walking Tour: Florence Noir and Its Secrets
- Florence Old City Street Food Tour and Guided Sightseeing
Still browsing? Here are more Florence experiences we've covered recently
- What Are The Best 2-Hour Tours In Florence? Our Top 3 Picks
- Our Picks For The 13 Best Wine Tours In Florence
- The 12 Most Popular Workshops & Classes In Florence
- The 11 Best Dining Experiences In Florence
- 14 Best Tours In Florence
- Florence’s 10 Best Dinner Experiences (With Prices & Reviews)
- 14 Best Walking Tours In Florence (With Prices)
- Florence’s 3 Best Hiking And Trekking Tours
- 7 Must-Try Private Driver Services In Florence
- Florence’s 14 Top Food Tours
- 14 Of The Best Photography Experiences In Florence
- Our Picks For The 13 Best Pasta Experiences In Florence
