Private Best of Tuscany Hill Towns Tour with lunch from Florence

Exploring Tuscany’s enchanting hill towns is a dream for many travelers, and this private tour from Florence aims to deliver just that. Covering Siena and San Gimignano in a single day, it combines scenic drives, medieval architecture, wine tasting, and a traditional Tuscan lunch—all in the comfort of a private vehicle with an expert guide.

What many appreciate most about this experience is the personalized attention from a knowledgeable driver-guide, making the day feel both intimate and insightful. You’ll get to wander through historic streets, climb towers with jaw-dropping views, and enjoy regional wines, all while avoiding the crowds typical of larger group tours.

However, some might find the nine-hour schedule a bit packed, especially considering the long drives and multiple stops. If you prefer a more relaxed pace or wish to spend more time sampling wines, this might feel a touch rushed. Still, for those wanting a comprehensive, authentic taste of Tuscany’s highlights, this trip offers impressive value.

This tour is ideal for travelers who appreciate personalized, small-group experiences, enjoy culture, and are eager to combine sightseeing with culinary delights. It’s also suitable for first-time visitors wanting an efficient way to see some of Tuscany’s most iconic spots without the hassle of planning.

Key Points

• Private, personalized experience with an English-speaking driver-guide
• Visits to Siena and San Gimignano, two of Tuscany’s most beloved medieval towns
• Includes wine tasting at a carefully selected vineyard
• Traditional Tuscan lunch provided, adding authentic regional flavors
• Comfortable transportation aboard a private Mercedes A/C minivan
• Scenic countryside drives with plenty of photo opportunities
• Tours are booked 125 days in advance on average, indicating popularity
• Highly rated with a 4.5/5 rating from 56 reviews

The Journey Begins: Setting Expectations

Starting out in Florence, you’ll meet your driver-guide early in the morning at Piazza della Repubblica—an ideal central spot. From there, the adventure begins with anticipation of the scenic drive through Tuscany’s rolling hills, dotted with vineyards, olive groves, and charming villages.

You’ll be traveling in a private Mercedes A/C minivan, meaning your group will enjoy comfort and space, a significant plus when spending nearly nine hours on the move. The driver-guide is fluent in English, sharing insights about the towns, the region’s history, art, and culinary traditions—making the entire experience educational as well as visual.

Exploring Siena: The Heart of Medieval Tuscany

Your first stop is Siena, famous for its Palio di Siena, a horse race that ignites this city twice a year. Although you might not coincide with the race, the city itself is a spectacle of medieval architecture, with its narrow streets, shell-shaped main square, and centuries-old palazzi.

One reviewer highlighted their guide’s personal touch, noting that the Siena guide Adele “showed us a personal side of the city,” taking us through neighborhoods and sharing lesser-known facts. This adds a layer of authenticity that’s often missing from larger group tours.

Expect to walk through the historic center, with a chance to admire sights like the Duomo di Siena if time permits, and listen to stories about the city’s past. The guide’s depth of knowledge makes these moments engaging, especially for history buffs.

San Gimignano: The Town of Towering Skylines

Next, the tour takes you to San Gimignano, often called the “Medieval Manhattan” for its skyline of medieval towers built by wealthy families as a display of power. These towers still dominate the landscape, offering stunning panoramic views from the Torre Grossa.

You’ll enjoy a leisurely walk, which many reviews describe as a “beautiful and picturesque” experience. Visitors often spend about 1.5 hours here, exploring the cathedral, snapping photos of the towers, and tasting gelato in Cistern Square—an unmissable treat according to reviews.

A common highlight is the climb up the Torre Grossa, which provides a breathtaking view of the Tuscan countryside. Reviewers mention that this town feels like a postcard, with its Gothic and Romanesque architecture giving a true sense of medieval Italy.

Wine Tasting and Tuscan Lunch: A Regional Feast

Perhaps the most appreciated part of this tour is the wine tasting at a carefully selected vineyard. Visitors often comment on the generous servings—sometimes almost a full glass or even a bottle’s worth—so come prepared if you prefer smaller tastes. The wines are described as “reasonable” and well-selected, making this a genuine introduction to Chianti’s offerings.

The Tuscan lunch is a shared experience—usually a platter of cheese, meats, and bread at the winery, with some reviews noting that it’s more like a tasting than a full meal. One reviewer appreciated the “meat and cheese platter for 15 euros”, emphasizing that it offered authentic regional flavors rather than a formal sit-down meal.

The combination of local wines and regional fare adds depth to the experience, making it not just about sightseeing but also about savoring Tuscan culture through food and drink.

The Scenic Return and Overall Experience

After a full day of exploring, tasting, and photographing, you’ll head back to Florence along scenic rural routes. Many reviews mention the beautiful landscape, perfect for photo stops and just soaking in the views. The tour concludes back at Piazza della Repubblica around 5 pm, giving you a full day of immersive experiences.

The feedback from travelers reflects high satisfaction—many appreciate the knowledgeable guides like Lorenzo and Fabrizio, who offer fun, friendly, and insightful commentary. The small-group vibe makes the tour feel intimate and flexible, allowing for personalized interaction.

How Does It Stack Up in Terms of Value?

At $662.98 per person, this tour might seem steep at first glance. However, considering the all-inclusive nature—private transportation, expert guide, visits to two major towns, wine tasting, and lunch—it offers a comprehensive, hassle-free way to see and taste Tuscany.

Guests frequently mention the dedication and friendliness of the guides, which can significantly enhance the experience. Plus, the convenience of door-to-door pickup and the avoidance of crowded bus tours are big pluses for many.

Final Thoughts

This private Tuscany hill towns tour offers a well-rounded day of exploration—combining history, architecture, regional wine, and authentic food—all in a comfortable and personalized setting. It’s particularly suited for travelers who prefer small groups or private experiences and want in-depth insights from passionate guides.

While the schedule can feel a little tight for those seeking a slower pace, the overall value lies in the quality of the experiences and the genuine regional flavor. If you’re after a memorable, culturally rich day without the crowds, this tour is a solid choice.

Who Would Love This Tour?

• First-time visitors looking for a curated experience of Tuscany’s highlights
• Travelers who value personalized attention and expert guidance
• Food and wine lovers eager to taste regional specialties in a scenic setting
• Those wanting a convenient, all-in-one day trip from Florence
• Photographers and scenery enthusiasts wanting picture-perfect views

FAQ

Is this a private tour?
Yes, this experience is exclusive to your group, ensuring a more intimate and personalized adventure.

What is included in the price?
Private transportation in a Mercedes A/C vehicle, an English-speaking driver-guide, visits to Siena and San Gimignano, a winery visit with wine tasting, and a Tuscan lunch.

How long does the tour last?
Approximately 9 hours, starting around 8 am and returning by 5 pm.

Are children allowed on this tour?
Yes, children can participate, but they must be accompanied by an adult.

What should I wear?
Dress appropriately for all weather conditions, especially since you’ll be walking in historic towns and climbing towers.

Can I customize the itinerary?
Since this is a small, private tour, your driver-guide can adapt the stops depending on your interests and timing.

Is there a specific order to the towns visited?
The itinerary may vary, and the sequence of Siena and San Gimignano might change based on logistics.

What if I need to cancel?
You can cancel for free up to 24 hours before the tour, and you’ll receive a full refund.

This tour offers a balanced mix of scenic beauty, culture, and regional flavors. Perfect for those wanting to get a true taste of Tuscany in a relaxed, yet enriching setting.