Private Tuscany Tour to Siena and San Gimignano with Winery Lunch

Key Points

• Price and Duration: Priced at $580.54 per person for an approximately 10-hour journey.
• Exclusive Experience: Private tour with only your group, led by a knowledgeable local guide.
• Highlights: Explore Siena’s historic streets, visit the Duomo, and wander San Gimignano’s towers, with free time at each destination.
• Exceptional Lunch: Enjoy a traditional Tuscan meal at a family-run organic winery, complete with wine tastings.
• Scenic Vistas: Admire countryside views from landmarks like La Rocca and the Rocca of Montestaffoli.
• Highly Rated: Consistently rated 5.0 out of 5 based on 20 reviews, praised for expert guides and delicious food.

Exploring Tuscany: Siena and San Gimignano in One Day

This private Tuscany tour from Florence offers a comprehensive experience of two of Tuscany’s most captivating hill towns, Siena and San Gimignano, with a highlight on local cuisine and wine. At $580.54 per person, the tour provides an all-inclusive day featuring guided walks, scenic drives, and delicious Tuscan fare.

Designed for those who want to skip the crowds and enjoy a personalized experience, this tour is led by a professional guide and offers pickup from Florence. The 10-hour itinerary balances sightseeing, tasting, and free time, making it ideal for history enthusiasts, food lovers, and photographers alike. Expect stunning views of vineyards and rolling hills, with plenty of opportunities to sample local wines and explore at your own pace.

How the Tour Starts and What You Can Expect

The day begins at 8:30 am with a meeting point in Florence, where an air-conditioned minivan awaits. Your expert guide introduces the day’s plan, sharing interesting facts about Tuscany’s history and culture as you depart towards Siena. The drive takes about an hour and 15 minutes, during which you’ll have the chance to settle in and get to know your fellow travelers.

The small group setting ensures a personalized experience, with pickup included and the option for mobile tickets for easy access. The focus here is on comfort and flexibility, with plenty of time scheduled for both guided sightseeing and free exploration.

Discovering Siena’s Medieval Charm

Upon arrival in Siena, the tour incorporates a 45-minute drive to the city, followed by a guided walking tour of one hour. Your local guide leads you through Siena’s beautiful streets, with highlights like the Duomo, featuring a floor made of over 50 images crafted over two centuries and considered one of Italy’s most stunning cathedrals.

You’ll visit Piazza del Campo, famous for its shell-shaped layout and the Palio horse race, a tradition that dates back over 600 years. The square is a lively hub where locals gather, and your guide explains the contrade—the 17 districts—and their symbolic animals like snails and giraffes, which embody the city’s deep-rooted community spirit.

A visit to the Monte dei Paschi di Siena, the oldest surviving bank in the world since 1472, offers insight into Siena’s wealth from banking during the pilgrim routes era. The tour finishes with free time—perfect for shopping, relaxing at a café, or exploring further.

Enjoying a Traditional Tuscan Lunch at an Organic Winery

After Siena, a 15-minute drive takes you to Fattoria Poggio Alloro, an organic family-run wine estate. Here, a hearty Tuscan lunch is served, featuring homemade pasta, cured meats, cheeses, and fresh farm vegetables. The meal is complemented by wine tasting of four varieties, available only to adults over 18.

The lunch setting offers stunning countryside views, making it a great chance to relax and savor authentic Tuscan flavors. Guests can also buy local products directly from the winery before moving on to San Gimignano.

Exploring San Gimignano’s Famous Towers

The afternoon is dedicated to San Gimignano, a UNESCO World Heritage Site renowned for its medieval towers. Once home to 72 towers, only 14 remain, giving the town its nickname, the Little Manhattan of Tuscany.

Your guide provides a map and tips as you have two hours of free time to explore on your own. Key landmarks include Piazza della Cisterna, known for its medieval charm and gelato shop Dondoli, famous for award-winning gelato.

Another highlight is Piazza del Duomo, where the collegiate church features colorful frescoes from the 14th century. For panoramic views, climb the Torre Grossa or visit La Rocca of Montestaffoli behind the Duomo, where the view over the towers is breathtaking.

The Scenic Drive Back to Florence

After a full day of sightseeing, a one-hour drive returns you to Florence, arriving around 5:45 pm. The journey is smooth, and the group often shares photos and stories, reflecting on the beautiful scenery, delicious food, and fascinating history experienced throughout the day.

The private nature of this tour ensures a customized, relaxed pace, with plenty of opportunities for photos, shopping, and enjoying the local atmosphere.

What Makes This Tour Stand Out

This private tour excels in providing a comprehensive Tuscany experience with personalized guidance. The expert guides receive high praise for their knowledge, friendliness, and storytelling skills, making history and culture come alive. The lunch at the organic winery is a standout feature, combining authentic food with fantastic wine and stunning countryside views.

The free time in both Siena and San Gimignano allows for independent exploration without feeling rushed, which is highly valued by past participants. The small group size fosters a relaxed atmosphere, ideal for conversation and spontaneous discoveries.

The tour’s high rating of 5.0 out of 5 and excellent reviews highlight its reliability and quality, especially for those interested in cultural sights and culinary delights.

Considerations and Practical Tips

While the tour offers a full day of sightseeing and tasting, travelers should be prepared for moderate physical activity, including walking and climbing towers. The provision of free time at key locations helps accommodate different pacing needs.

Note that wine tasting is only for those 18 and older, and comfortable walking shoes are recommended, especially for exploring Siena and San Gimignano’s cobbled streets. The pickup is included, and mobile tickets simplify access on the day.

Final Thoughts on the Tuscany Private Tour

This well-organized, highly-rated tour delivers a balanced mix of history, scenery, and gourmet experiences. It suits history buffs, foodies, and those seeking a personalized tour away from large groups. The guides’ knowledge and friendly approach are consistently praised, making the day both informative and enjoyable.

The lunch at the organic winery and free time in the towns add genuine value, creating a relaxed atmosphere to absorb the charm of Tuscany. While the itinerary is tightly packed, the small group size and flexible pacing make for a comfortable, memorable day.

This tour offers a trustworthy, immersive way to experience Siena and San Gimignano with the best of Tuscan cuisine and scenery included.

Frequently Asked Questions

Is the tour suitable for all ages?
Yes, but wine tasting is only available for guests over 18.

What is included in the lunch?
A traditional Tuscan meal with organic farm food, including homemade pasta, cured meats, cheeses, and fresh vegetables, with wine tastings.

How long is the drive from Florence to Siena?
Approximately 1 hour and 15 minutes.

Can I explore Siena and San Gimignano independently?
Yes, the tour provides free time at each town for self-guided exploration.

Is this tour wheelchair accessible?
The data suggests moderate physical activity; travelers should have moderate fitness levels.

What should I bring?
Comfortable walking shoes and a camera for photos are recommended.

Are dietary options available?
Yes, the lunch accommodates vegetarian and gluten-free options.

What is the tour guide’s role?
The guide leads guided walks, explains local history, and provides insider tips.

How do I cancel the tour?
You can cancel free of charge up to 24 hours in advance for a full refund.

What if it rains?
The tour can proceed in rainy weather, as the stops are mostly indoor or covered; past reviews note that the experience remains enjoyable despite rain.