Private Tuscany Tour to Siena and San Gimignano with Winery Lunch

Imagine exploring two of Tuscany’s most iconic towns—****Siena and San Gimignano—in one day, with a guided walk, a delicious organic farm lunch, and wine tasting, all while enjoying scenic countryside views. For around $580, you’ll spend about 10 hours immersed in history, stunning scenery, and authentic tastes, with a professional guide and a private vehicle making the experience comfortable and personalized.

What we really love about this tour is how flexible and relaxed it feels—your guide gives you plenty of free time to explore each town at your own pace, plus the chance to enjoy a family-run winery in serene surroundings. The second standout? The insider look into Siena’s unique contrade neighborhoods and the opportunity to sample some of the best gelato in San Gimignano.

One aspect to keep in mind: this is a full day, and while the pace is typically manageable, it involves some walking and standing, so it’s best suited for travelers with moderate mobility. If you’re after a seamless, authentic experience that combines sightseeing, local food, and wine—all without the hassle of planning—you’ll find this tour is a fantastic value.

It’s especially well-suited for those who want a comprehensive taste of Tuscany’s culture, history, and landscape in one day, with an emphasis on small-group intimacy and expert guiding.

Key Points

• Comfortable private transportation ensures a stress-free journey between towns and sights.
• Flexible free time in Siena and San Gimignano allows for personal exploration and shopping.
• Authentic local experiences like visiting a family-run vineyard and sampling organic farm-to-table cuisine.
• Deep dives into Siena’s unique contrade neighborhoods and its famous Piazza del Campo.
• Spectacular panoramic views from La Rocca and Rocca of Montestaffoli.
• Expert guides enrich the experience with stories, history, and insider tips.

An Authentic Day in Tuscany: Siena, San Gimignano, and a Winery Lunch

When we think about Tuscany, images of rolling hills, medieval towers, and hearty wine come to mind. This private tour from Florence brings those images to life with visits to two of the most enchanting towns—Siena and San Gimignano—plus an organic winery lunch that’s as much about flavor as it is about scenery.

For a set price of about $580, you’ll spend roughly 10 hours with an expert guide, traveling comfortably in an air-conditioned vehicle. The tour’s design balances guided sightseeing with leisure, giving you the chance to wander independently and soak up the atmosphere. It’s a carefully curated experience that appeals to travelers seeking a mix of cultural insight, stunning views, and genuine local flavors.

Who Will Love This Tour?

Travelers who enjoy small-group experiences with personalized attention, are keen to learn stories behind historical sites, and appreciate authentic Tuscan food and wine will find this tour a perfect fit. It’s also ideal for those who want the convenience of transportation and a flexible schedule, ensuring they see highlights without feeling rushed.

The Itinerary in Detail

The Drive from Florence to Siena

Your day begins with a pickup in Florence. Your guide, whose enthusiasm and knowledge shine through reviews, will explain what’s ahead and entertain you with interesting facts. The drive takes about 1 hour and 15 minutes. Expect scenic views of vineyards and rolling hills—why Tuscany is considered one of Italy’s most beautiful regions.

Exploring Siena

Once in Siena, you’ll join a guided walk through the city’s most beautiful streets and sites, including the Siena Cathedral with its stunning artwork and floor marbles, and Piazza del Campo, a shell-shaped square famous for the Palio horse race. Siena’s contrade neighborhoods are a highlight, with local guides explaining the significance of the animal symbols and community pride.

One review sums it up: “The sense of identity and belonging to one’s contrada is extremely important,” which adds a layer of local color to your visit. You’ll also stop at Piazza Salimbeni, home to the world’s oldest bank, Monte dei Paschi di Siena, giving insight into Siena’s historic wealth through banking.

Inside Siena’s Duomo

Entering the cathedral is a must. Its floor mosaics, created over two centuries by notable artists, make it a real masterpiece. The interior with its vibrant frescoes offers a visual feast, and many find it more impressive than Florence’s Duomo. After exploring, you’ll have some free time to shop or relax at a café.

The Winery and Lunch at Fattoria Poggio Alloro

A short drive takes you to this organic, family-run wine estate, where the focus is on sustainable, farm-to-table practices. Here, you’ll enjoy a traditional Tuscan lunch with homemade pasta, cured meats, cheeses, and fresh garden salads—plus wine tasting of four varieties. The setting, with panoramic countryside views, makes this a memorable culinary stop.

Reviewers rave about the food: “Lunch at an organic wine farm was delicious,” and the wine tasting is a highlight, immersing you in Tuscany’s famous viticulture. The opportunity to purchase local products adds to the authentic feel.

San Gimignano: The “Manhattan of Tuscany”

After lunch, it’s time to visit this UNESCO World Heritage Site, renowned for its medieval towers—initially 72, now just 14 remain. From the Rocca of Montestaffoli, you’ll witness breathtaking panoramic views of San Gimignano’s skyline.

You’ll receive a map to explore independently, focusing on the main sights, including the Piazza della Cisterna and the Piazza del Duomo. Here, you can indulge in the famous gelato at Gelateria della Piazza, awarded for having the best gelato in the world.

Climbing and Views

The Torre Grossa offers a chance to climb a medieval tower for an amazing bird’s-eye view of the town. Meanwhile, La Rocca provides another peaceful spot for photos and a quiet walk among olive trees and ruins, where the views of the towers are simply spectacular.

Returning to Florence

After a full day of exploring, your driver will take you back to Florence, completing the loop in about one hour. You’ll arrive with a camera full of pictures, a stomach satisfied with authentic Tuscan cuisine, and a mind full of stories.

Why This Tour Is a Great Deal

Considering the inclusion of guided walks, private transportation, a farm lunch, wine tasting, and free time at each stop, the value here is impressive. The reviews consistently praise the knowledgeable guides who add depth to visits, making history and local customs come alive. The scenic drives and stunning viewpoints are prime highlights, especially for those who love landscape photography or simply want a taste of Tuscany’s beauty.

The small group size and private vehicle create a personalized, relaxed atmosphere that larger tours can’t match. Plus, booking 111 days in advance indicates this experience is in high demand, and for good reason.

Potential Drawbacks

The main consideration is the full-day duration, which might be tiring for some, especially if you prefer a slower travel pace or have mobility concerns. The itinerary is packed, but the balance of guided tours and free time helps counteract this.

Final Thoughts

This private Tuscany tour offers a well-rounded glimpse into two iconic towns, combined with a memorable farm-to-table lunch and wine tasting. It’s perfect for travelers who want to see the highlights without sacrificing authenticity or comfort. The focus on local guides, scenic views, and delicious food makes this experience stand out.

If you’re looking for a day that combines history, stunning vistas, and genuine Tuscan flavors in a relaxed and personalized setting, this tour is a smart choice. It’s especially suited for curious travelers eager to learn stories behind the sights and indulge in regional specialties.

FAQs

What towns does the tour visit?
It visits Siena and San Gimignano, two of Tuscany’s most famous medieval towns.

How long is the drive between Florence and Siena?
About 1 hour and 15 minutes each way, offering scenic views of vineyards and hills.

Is there free time in Siena and San Gimignano?
Yes, you’ll have several hours for independent exploration, shopping, and relaxing, after guided tours.

What is included in the lunch?
A traditional Tuscan farm lunch with organic, homemade food, and wine tasting of four varieties—vegetarian and gluten-free options available.

Is this tour suitable for children or those with mobility issues?
It requires moderate physical activity like walking and standing, so travelers with mobility concerns should consider this.

Can I buy local products at the winery?
Yes, there’s an opportunity to purchase local wines and products before heading back to Florence.

What is the size of the tour group?
Since it’s a private experience, only your group participates, ensuring a personalized and flexible day.

Does the tour operate rain or shine?
Yes, the experience proceeds regardless of weather, though some outdoor activities may be affected.

How far in advance should I book?
On average, travelers book about 111 days ahead, highlighting its popularity.

In essence, this tour balances expert guiding, scenic beauty, and authentic Tuscan flavors, making it a worthwhile choice for those wanting a comprehensive day trip from Florence.