PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

Key Points

• Private experience for up to 8 people, led by a knowledgeable guide and driver
• Includes visits to Siena’s Piazza del Campo and Siena Cathedral, San Gimignano’s medieval towers, and Monteriggioni’s fortified walls
• Optional lunch at an organic Chianti winery, paired with local wines and organic specialties
• Luxury transportation in a Mercedes minivan offers comfort and convenience
• Flexible timing with departure around 9:00 am and personalized schedules
• Highly praised for friendly guides, smooth logistics, and memorable views

Introduction to the Full-Day Tuscan Adventure from Florence

This private tour from Florence offers an immersive exploration of some of Tuscany’s most iconic medieval towns and scenic landscapes. Priced at $377.35 per person, the experience lasts roughly 8 to 9 hours and is designed for small groups of up to 8 participants. The tour is highly rated, with a perfect 5.0 out of 5 based on 208 reviews, emphasizing its excellent value, personalized service, and expert guidance.

The tour begins with convenient door-to-door pickup, allowing you to relax and enjoy the ride without worrying about navigation or public transport. The focus is on providing a luxurious and informative day, with many reviewers praising the guide’s friendliness and knowledge. An optional lunch at a Chianti organic farm adds a culinary highlight, showcasing regional flavors between historical stops.

Exploring Siena’s Medieval Charm and Architectural Marvels

The first stop in this full-day adventure is Siena, one of Tuscany’s most visited towns. Known for its medieval architecture, rich history, and lively Piazza del Campo, Siena is where you’ll find the Siena Cathedral of Santa Maria Assunta. This Italian Gothic masterpiece dominates the town square and is a major highlight with its spectacular design and historical significance.

In your two-hour visit, you’ll have time to stroll through the historic streets, browse local shops, and soak in the atmosphere. The Piazza del Campo captivates with its unique seashell shape, and it’s the venue for the famous Palio di Siena horse race twice a year. The cathedral offers an impressive glimpse into religious and architectural history, making Siena a perfect introduction to Tuscany’s medieval legacy.

Monteriggioni’s Fortress Walls and Short Walks

Next, the tour takes you to Monteriggioni, a charming fortified village still encircled by its original medieval walls. Located close to Siena, Monteriggioni offers a short but memorable stop where you can walk around this well-preserved fortress. The village’s medieval walls provide excellent photo opportunities and a sense of stepping back in time.

This two-hour stop is ideal for a quick exploration and offers a chance to enjoy a short walk through the narrow streets of this historic spot. While no admission fee is required, the walk allows for a glimpse into Tuscan medieval defense architecture and local village life.

Indulging in Organic Flavors at Marronaia Wine Garden

One of the tour’s standout options is the lunch at an organic winery, which is not included in the base price but highly recommended. Set at a biodynamic farm with panoramic views of San Gimignano’s towers, this two-hour experience features organic specialties, such as fresh pasta, crostini, local meats and cheeses, and seasonal vegetables.

The lunch is paired with Super Tuscan, Chianti, and Vernaccia wines, providing a genuine taste of the region’s wine culture. Travelers appreciate the spectacular setting among olive groves and vineyards, making this not just a meal but a culinary highlight of the day. Note that lunch costs an additional €55–65 per person, and opting for this may exclude access to Monteriggioni.

San Gimignano’s Tower Skyline and Ice Cream Delights

The final stop is San Gimignano, often called the “Manhattan of the Middle Ages” because of its skyline of medieval towers. This UNESCO-listed town offers a glimpse into 1300 AD with its well-preserved architecture. The tall towers dominate the horizon and are a major draw, with the Dondoli ice cream shop nearby earning international fame for its award-winning gelato.

Travelers are encouraged to walk freely through San Gimignano’s historic streets, explore shops, or climb a tower for panoramic views. This two-hour visit provides ample time to admire the medieval skyline and enjoy the vibrant atmosphere.

Comfort and Personalization in a Mercedes Minivan

Transportation during this tour is provided in a luxury Mercedes minivan, ensuring a comfortable and smooth journey. The vehicle accommodates up to 8 people, making it ideal for small groups or private parties seeking a personalized experience.

Multiple reviewers highlight the professionalism, friendliness, and knowledge of the driver-guide, who not only ensures safety but also shares insights about the Tuscan countryside and towns. The door-to-door pickup further enhances convenience, allowing guests to relax and focus on the sights.

Expert Guidance and Flexible Schedule

This tour features a private guide and driver, offering a tailored experience with plenty of opportunities for breaks, photos, and questions. Reviews emphasize the enthusiasm and expertise of guides like Alessandro, who is praised for his knowledge of wines, local history, and regional culture.

Departure is suggested around 9:00 am, with flexible pick-up times available during the reservation process. The small group size ensures a personalized pace, with time allocated at each stop for exploration or rest.

Practical Details and Booking Considerations

Booking this tour 118 days in advance is common, reflecting its high demand and popularity. The full refund policy allows cancellations up to 24 hours before the scheduled start, providing peace of mind. The tour includes mobile tickets, group discounts, and pickup service.

While the guide is not included in the core package, optional lunch at the winery can be arranged for an additional €55–65 per person. Keep in mind that minors under 18 are not permitted to participate in wine tasting, and the tour is limited to private groups, ensuring an intimate experience.

Why Choose This Tour: Strengths and Considerations

This full-day Tuscany trip from Florence is ideal for those who want a comprehensive, personalized, and luxuriously comfortable experience. The itinerary balances historical exploration, gastronomic delights, and scenic drives, all led by an enthusiastic and knowledgeable guide.

The small group size and private transportation make it perfect for travelers seeking flexibility and individual attention. The optional lunch adds a memorable culinary dimension, especially for wine lovers.

However, those wanting guided city tours in Siena or San Gimignano might find this experience more about sightseeing and less about guided walking tours. It’s best suited for visitors who prefer comfort, flexibility, and in-depth local insights without the hassle of self-driving.

The Sum Up: The Ideal Tuscan Day Trip for Private Groups

This private full-day tour from Florence offers a relaxed yet enriching way to experience Tuscany’s highlights. With visits to Siena’s Piazza del Campo, Monteriggioni’s medieval walls, and San Gimignano’s towers, combined with the option for a wine and organic lunch, it captures the region’s essence.

The luxury transport and personalized guide service have garnered excellent reviews for friendly, knowledgeable guides and seamless logistics. It suits small groups, couples, or families looking for a comfortable, flexible, and memorable day in Tuscany.

While the price reflects the private, exclusive nature of the tour, it promises a full immersion in Tuscany’s culture, history, and flavors — perfect for those who value quality and convenience.

Frequently Asked Questions

What is the price per person for this tour?
The tour costs $377.35 per person, with optional lunch in a Chianti winery available at an additional €55–65 per person.

How long does the tour last?
The tour lasts approximately 8 to 9 hours, departing around 9:00 am and ending in Florence.

Is transportation included?
Yes, luxury Mercedes minivan transport is provided with door-to-door pickup and space for up to 8 people.

Can the lunch be booked in advance?
Yes, the lunch at the winery can be organized during the reservation, and it includes organic specialties and local wines.

Are guides included on this tour?
The tour features a private guide and driver, with guides praised for their knowledge and friendliness. The guide is not a formal city guide but provides informative commentary during the drive and stops.

Is this tour suitable for children?
Minors under 18 years old are not allowed to participate in wine tasting, but they can join the sightseeing portions of the tour.

What are the main stops on this tour?
Stops include Siena, Monteriggioni, the optional winery lunch, and San Gimignano.

What should I bring?
Comfortable clothing, a camera, and a desire to enjoy Tuscany’s sights and flavors. Umbrellas are provided in case of rain.

Can I cancel this tour?
Yes, free cancellation is available up to 24 hours before the start time for a full refund.