Private Tuscany Tour to Siena and San Gimignano with Winery Lunch

If you’re planning a trip to Florence and craving a day full of breathtaking views, medieval charm, and delicious local food and wine, this private Tuscany tour hits the spot. It combines the best of both worlds: guided exploration with enough free time to truly soak in the atmosphere of Siena and San Gimignano, plus a memorable farmhouse lunch at a family-run winery.

What really makes this experience stand out is the seamless blend of guided sightseeing with relaxed, independent wandering—plus a focus on authentic, local flavors. The fact that it’s a private tour means you’ll have personalized attention and the flexibility to customize your day a little, which adds a nice touch of luxury.

One thing to keep in mind is that this tour is about 10 hours long and involves quite a bit of walking and driving. If you’re not keen on long days or have mobility considerations, it’s worth planning accordingly. Still, it’s suited best for travelers eager to explore Tuscany’s iconic towns with a deep appreciation for history, culture, and good food.

Key Points

• Customizable and private experience for a more personal and flexible day.
• Excellent value for money considering the guided tours, lunch, and wine tastings included.
• Stunning scenery en route, with views over vineyards and rolling hills.
• Authentic experience at a family-run winery with homemade Tuscan dishes.
• Rich cultural insights during guided walks through Siena and San Gimignano.
• Ample free time to explore each town at your own pace.

Why This Tour Will Appeal to You

This tour is ideal if you’re looking for a well-rounded, immersive day in Tuscany — not just ticking off sights but truly experiencing the region’s flavors and history. It’s especially suited for those who value small-group intimacy and guided insights but also appreciate some solo wandering. Food and wine lovers will enjoy the organic farm lunch, and history buffs will find plenty of intriguing stories about Siena’s banking past and medieval architecture.

The tour strikes a good balance between structured sightseeing and free exploration, making it perfect for travelers who want both guidance and independence. It’s also a great choice if you want a full day experience without feeling rushed or overwhelmed.

A Deep Dive into the Itinerary

Departure from Florence

Your day begins bright and early at 8:30 am, with a meet-up point in Florence. The air-conditioned minivan ensures a comfortable journey, and your guide will set the tone with engaging stories about Tuscany’s landscape and history. The drive to Siena takes about 1 hour and 15 minutes, providing plenty of time to get excited for what’s ahead.

Siena: the Medieval Jewel

Once in Siena, you’ll enjoy a guided walking tour that lasts around an hour. Your guide—someone with a wealth of local knowledge—will lead you through the city’s most beautiful streets and landmarks, diving into Siena’s fascinating history.

Highlights include the Piazza Salimbeni, home to the oldest bank in the world, Monte dei Paschi di Siena, founded in 1472. As the reviews mention, the city’s wealth once thrived from being on the pilgrim route of the Via Francigena, which helped Siena develop a prosperous banking industry. You’ll learn about this history firsthand as your guide explains how Siena’s banking roots still influence its identity today.

Next, you’ll explore Siena’s contrade—the unique districts with their own symbols and traditions. Reviewers note that visiting a church and museum of a contrada offers a glimpse into Siena’s deep sense of community and identity.

The Piazza del Campo, with its distinctive shell shape, is the heart of Siena and home to the famous Palio horse race. Walking here, you can imagine the vibrant energy during race days, which occur twice a year and are still a major event. Inside the Siena Duomo, you’ll see the awe-inspiring marble floor with intricate artwork—something that many reviewers highlight as a must-see.

Lunch at a Family-Run Winery

After exploring Siena, your journey continues to the Fattoria Poggio Alloro, an organic estate where a hearty, farm-fresh Tuscan lunch awaits. The meal features homemade pasta, cured meats, cheeses, and fresh garden salads, paired with local wines—an experience reviewers describe as both delicious and authentic.

The winery tour and tasting includes four varieties of wine, exclusively for guests 18 and over. Guests often remark on the breathtaking countryside views during lunch, making it not just a meal but a memorable scenic experience.

San Gimignano: the Towered Town

Post-lunch, you’ll head to San Gimignano, a UNESCO World Heritage Site famous for its medieval towers—originally 72, now just 14 remain, earning it the nickname the “Manhattan of Tuscany.” The town’s skyline, with its soaring towers, is an incredible sight, especially from viewpoints like La Rocca.

Your guide will provide a map and highlight key landmarks such as Piazza della Cisterna, known for its lively atmosphere and having some of the best gelato in the world at Gelateria della Piazza. Reviewers rave about the gelato, often citing it as a highlight of their visit.

Inside the Duomo, you’ll find stunning 14th-century frescoes, and climbing Torre Grossa offers panoramic views over the town. La Rocca provides yet another vantage point to admire the towers and rolling Tuscan landscape, often described as breathtaking.

Return to Florence

Your day wraps up with a scenic drive back, arriving in Florence around 7 pm. Travelers praise the well-organized schedule and the ability to explore at your own pace, with plenty of time to shop or relax in each town before heading home.

Transportation, Guides, and Group Size

The private nature of this tour means that only your group will participate, making for a more relaxed and personalized experience. The vehicle is air-conditioned, ensuring comfort throughout the approximately 10-hour journey.

The guides receive high praise for their knowledge, friendly manner, and ability to weave entertaining stories into the sightseeing. Several reviews mention guides like Stefano, Sara, and Francesca, who are described as professional, warm, and eager to share their love of Tuscany.

The tour is designed for travelers with a moderate physical fitness level—expect some walking and stair climbing, especially when visiting the cathedral and tower viewpoints. The tour accommodates plenty of free time allowing you to explore independently, shop for local products, or simply relax in a piazza.

Cost and Value

Priced at around $580 per person, this tour offers significant value given the inclusion of guided city walks, a traditional Tuscan lunch with wine, and visits to two iconic towns. The reviews underscore the quality of the guides, the delicious lunch, and the breathtaking scenery, making the price a reasonable investment for a full, curated Tuscany experience.

Final Thoughts: Is This Tour Right for You?

If you’re after a comprehensive day that balances guided cultural insights with free exploration, this tour is a fantastic choice. It’s particularly suited for travelers who want to learn about Tuscany’s history, enjoy authentic food and wine, and see two of the region’s most beloved towns without the hassle of organizing transport or tickets.

The small-group format is perfect for those seeking intimacy and flexibility, while the expert guides ensure you gain deeper understanding beyond just sightseeing. Remember, it’s a long day, but with such a well-paced itinerary and stunning scenery, you’ll likely feel it’s worth every minute.

Wine lovers, history enthusiasts, and those craving a taste of medieval Italy will find this tour a highlight of their trip. It offers a genuine, well-rounded taste of Tuscany’s best offerings—beautiful towns, delicious food, and warm, knowledgeable guides.

FAQ

Is this tour suitable for children?
While the tour is designed for adults, children who can comfortably handle a full day of walking and car rides will enjoy the sights and stories. However, wine tasting is only for guests 18 and over.

What is included in the lunch?
The farm lunch features homemade pasta, cured meats (including prosciutto and salami), cheeses, garden salads, and Tuscan biscotti. Vegetarian and gluten-free options are available.

How much free time do I get in Siena and San Gimignano?
You’ll have plenty of free time to explore independently—about 3 hours in Siena after the guided tour, and 2 hours in San Gimignano, which is enough to visit key landmarks, shop, or relax.

Is transportation comfortable?
Yes, the tour uses an air-conditioned minivan, providing a comfortable ride between locations. The drive offers scenic views and a chance to relax.

How many people typically join this tour?
Being a private tour, only your group participates. This ensures a more personalized experience, and the reviews highlight how guides like Stefano or Sara foster friendly, engaging atmospheres.

Can I customize the itinerary?
The tour is fixed in its main stops but offers some flexibility within the schedule, especially during free exploration times.

What is the cancellation policy?
You can cancel for free up to 24 hours before the tour, receiving a full refund. Last-minute cancellations are non-refundable.

Is there any age restriction?
Yes, wine tasting is only for guests 18 and over. Other parts of the tour are suitable for most ages with moderate physical activity.

How do I book this tour?
You can reserve through Viator or directly with Walkabout Florence Tours. Confirmations are sent immediately upon booking.

This private Tuscany tour combines the best sights, flavors, and stories of Siena and San Gimignano into one memorable day. Whether it’s your first visit to the region or a return trip, you’ll find plenty to love in this thoughtfully curated experience.