Private tour Siena, San Gimignano and Monteriggioni, lunch in the cellar

If you’re dreaming of a day exploring Tuscany’s iconic towns with a flexible, personalized touch, this private tour from Florence might just be your ideal escape. It offers a full itinerary that includes Siena’s historic streets, the fairy-tale walls of Monteriggioni, and the medieval skyline of San Gimignano, all with the comfort of private transportation and an expert guide.

What we love most is the opportunity to customize your day with plenty of free time in each destination—perfect for wandering at your own pace or snapping those Instagram-worthy shots. The highlights are definitely the stunning panoramic views, the in-depth stories from your guide, and the chance to indulge in local wines and authentic Tuscan flavors (lunch not included but highly recommended).

One potential consideration is the price point, which might seem steep for some travelers, especially since lunch and wine tasting are extra. However, for those seeking a private, intimate experience that offers both culture and scenic beauty, the value can be well worth it. This tour suits those who appreciate history, photography, wine, and a flexible itinerary—perfect for couples, small groups, or those wanting a tailored Tuscan adventure.

Key Points

• Personalized Experience: Private guide and transportation mean total flexibility and a customized schedule.
• Historic Towns: Visit Siena’s UNESCO-listed Piazza del Campo and Gothic Basilica, plus San Gimignano’s medieval towers.
• Scenic Stops: Monteriggioni’s fairy-tale castle walls offer a memorable photo op and a glimpse into medieval life.
• Wine & Lunch: Optional wine tasting and lunch at a family-run winery provide a taste of authentic Tuscan hospitality.
• Comfort & Convenience: Air-conditioned vehicle, WiFi on board, bottled water—traveling in style and comfort.
• Authentic Insights: Our reviews highlight knowledgeable guides and insider tips, enriching the experience.

An In-Depth Look at the Tour Experience

Starting Point – Florence

Your day begins with a convenient pickup in Florence, where your private guide and driver will greet you. The vehicle is air-conditioned with WiFi, making the journey both comfortable and connected. From the start, you’ll notice the smooth ride and the personal attention that sets this tour apart from larger group excursions.

Siena: The Heart of Tuscany

After about an hour’s drive, you arrive in Siena, a city that feels like stepping into a living museum. Here, you’ll explore the Basilica of San Domenico, renowned for its Gothic architecture and the relic of Santa Caterina, the city’s patron saint. One reviewer comments, “Florian pointed out different places and gave great background information,” emphasizing the guide’s knowledgeable narration.

A highlight is walking through Piazza del Campo, a UNESCO World Heritage site famous for the Palio horse race. The square’s shell-shaped layout and historic buildings make it one of Italy’s most atmospheric spots. While the tour offers an outside view of Siena’s Duomo, an internal visit isn’t included—something to keep in mind if you’re a cathedral enthusiast.

Monteriggioni: The Enchanted Castle

Next, a short 25-minute drive takes you to Monteriggioni, a small village that feels like it belongs in a storybook. The walls and towers evoke images of fairy tales, making it a perfect spot for photos or a leisurely stroll. Reviewers mention that “the impression that remains in the memory, however, lasts forever,” highlighting its almost magical vibe.

In just 30 minutes, you get an authentic taste of medieval life, with the chance to walk around the walls and imagine what life was like centuries ago. It’s a quick stop but one that leaves a lasting impression due to its charming, well-preserved state.

Fattoria Sant’Appiano: Wine Tasting and Lunch

From Monteriggioni, the tour continues to a family-run estate—Fattoria Sant’Appiano—for a relaxed wine tasting and a farm-to-table lunch (not included in the price). This stop is highly praised for the delicious food and excellent wines. One reviewer calls it a “highlight,” noting the “delicious lunch and wine tasting in the cellar.”

Though the lunch is an optional add-on, many find it to be a memorable part of the day, offering a genuine glimpse into Tuscan hospitality. The guide’s recommendation here is invaluable, as local family wineries provide authentic flavors that big commercial tours might overlook.

San Gimignano: The Medieval Skyline

Your journey then takes you to San Gimignano, a UNESCO site famed for its medieval towers and preserved architecture. You’ll have about an hour to explore this charming town, which has changed little since the 14th century. Expect picturesque streets, historic buildings, and plenty of spots to soak in the atmosphere.

Reviewers rave about the views, with one mentioning how Florian’s commentary made the visit “very informative,” and another highlighting that “the town has remained almost intact from the end of the fourteenth century.” The town’s skyline, dotted with towers, offers fantastic photo opportunities, especially from viewpoints like Piazzale Michelangelo—a perfect end to your sightseeing.

Return to Florence

The tour concludes with a scenic drive back to Florence, where the guide will drop you off at your original pickup point. The seamless, private experience ensures you end your day relaxed, with plenty of memories—and perhaps some wine bottles—packed away.

Practical Details and Value

Transportation & Comfort

The private vehicle is a major perk—air-conditioned, WiFi-equipped, and spacious enough to keep everyone comfortable. The driver, Florian, receives glowing reviews for his professionalism, knowledge, and friendliness, making the entire journey more engaging.

Duration & Group Size

Spanning approximately 8 to 9 hours, the tour offers an immersive experience without feeling rushed. It’s designed for groups up to 7, ensuring a personalized touch that larger tours can’t match.

Cost & What’s Included

At $887.34 per group, the price might seem high but consider the value of private transport, personalized attention, and flexible planning. Admission to Siena’s Basilica and external view of Siena’s Duomo are included, but the tasting and lunch are extra, giving you the flexibility to choose based on your preferences.

Reviews & Authentic Experiences

Guests consistently praise Florian for his knowledge, patience, and ability to share interesting insights. Many mention the wine tasting and lunch as highlights, with reviews emphasizing the delicious food and the genuine atmosphere of the winery. The small-group setting means you’ll get a lot of attention and tailored stories—perfect for those who love deep dives into local culture.

The Sum Up: Who Will Love This Tour?

This private tour offers a mix of cultural exploration, scenic beauty, and local flavor that appeals most to travelers craving a personalized, authentic experience. It’s ideal for those who want the flexibility to explore at their own pace, enjoy expert commentary, and indulge in regional wines and cuisine. Small groups and families will find this especially rewarding, as the private setting fosters a relaxed, intimate atmosphere.

If you value high-quality guides, stunning views, and a genuine taste of Tuscany, this tour checks all those boxes. It’s particularly well-suited for travelers with limited time in Florence who want a comprehensive yet personalized day trip through some of Tuscany’s most iconic towns.

However, keep in mind the extra costs for wine tasting and lunch, and consider whether you prefer a more budget-friendly or all-inclusive experience. Overall, for those who want a tailored, comfortable, and insightful tour, this private day trip delivers on all fronts.

FAQ

Is this tour private?
Yes, this is a private tour, meaning only your group participates, providing a more personalized experience.

What’s included in the price?
Private transportation, air conditioning, WiFi on board, bottled water, and an English-speaking driver are included. Entrance to Siena’s Basilica is also covered.

Are meals or tastings included?
No, lunch and wine tasting at the winery are not included but are available as optional extras.

How long is the tour?
The tour lasts approximately 8 to 9 hours, giving ample time to explore each stop without feeling rushed.

Can children participate?
Most travelers can participate, and you can request a child seat during booking for families.

What kind of vehicle is used?
A comfortable, air-conditioned private vehicle equipped with WiFi ensures a smooth ride.

Is there time to shop or explore on your own?
Yes, each stop offers free time where you can wander, shop, or take photos at your own pace.

What’s the guide like?
Based on reviews, Florian is praised for his patience, knowledge, and friendly attitude, enriching the experience with stories and insights.

Do I need to book in advance?
Yes, most travelers book around 74 days in advance, especially during high season.

What if I need to cancel?
You can cancel free of charge up to 24 hours before the tour for a full refund.

This tour combines the best of Tuscany’s history, scenery, and flavors, wrapped in a flexible, private package that ensures you get the most out of your day. Whether you’re a history buff, a photographer, or a wine lover, it’s a well-rounded way to enjoy Tuscany’s highlights without the hassle of crowds or rigid schedules.