From Florence: PRIVATE Siena and San Gimignano with wine tasting

A Deep Dive into the Florence to Tuscany Private Tour: Siena, San Gimignano, and More

If you’re considering a full-day escape from Florence to explore the heart of Tuscany, this private tour promises to take you beyond the typical tourist trail. While I haven’t personally experienced it, reviews and detailed descriptions paint a picture of a well-organized, personalized adventure that balances sightseeing with relaxed indulgence.

What really stands out are the knowing guides and the carefully curated stops, especially the opportunity to enjoy wine tasting in a local winery. Another plus is the flexibility of free time in each location, allowing you to explore at your own pace—something not always possible with larger group tours.

That said, one thing to keep in mind is that this tour doesn’t include hotel pickup or drop-off, so you’d need to arrange your own transport to and from the meeting point. Overall, it seems best suited for travelers who want a luxurious, intimate experience with knowledgeable guides and a focus on Tuscan culture—perfect for those who appreciate comfort but still want to see a lot in one day.

Key Points

• Private and personalized experience, with your own group
• Includes lunch and wine tasting, adding a culinary touch
• Comfortable transportation in a luxury van with an English-speaking driver
• Flexible free time at each stop for personal exploration
• Ideal for lovers of wine, history, and scenic views
• No hotel pickup; you’ll need to meet at the starting point

What to Expect from the Tour

This full-day trip runs roughly 9.5 hours, starting bright and early at 8:00 am, with a pickup point at Florence’s Piazza degli Antinori. The journey whisks you off in a plush, air-conditioned van with your own driver and guide, meaning you’re in good hands from the start.

Siena: Medieval Charm and Local Delights

Your first stop is Siena, a city that immediately transports you to the Middle Ages. You’ll be greeted by a local guide who will lead you through the city for about an hour, hitting highlights like the famous Piazza del Campo and the Piazza del Duomo. These spots are the essence of Siena—with their striking architecture and lively atmosphere, you’ll feel like you’ve stepped back in time.

Fans of architecture and history will love the opportunity to walk these streets at a relaxed pace. You’re free to spend an additional hour exploring the Duomo, shopping, or just soaking up the medieval vibe. The reviews rave about the local guide, Maria, who is described as very knowledgeable, making the experience both informative and engaging.

Monteriggioni: A Castle in a Fairy Tale

Next, the tour heads to Monteriggioni, a tiny fortress town built in 1213. Its walls inspired Dante Alighieri, who mentioned the town in the Divine Comedy. The standout here is the chance to sit down for a lunch paired with local wines in a scenic setting, which travelers say is truly memorable.

You’ll spend about an hour and a half in Monteriggioni, enjoying the food, the views, and the sense of stepping into a storybook. Many reviews highlight how the lunch — included in the tour — feels authentic and special, giving you a real taste of Tuscan hospitality.

San Gimignano: The Town of Towers

As you make your way toward San Gimignano, the landscape unfolds into classic Chianti scenery—rolling vineyards, olive groves, and golden fields. Once there, you’ll have about an hour and a half to explore this UNESCO-listed medieval town, famous for its towers that dominate the skyline.

Walk the narrow streets, peek into shops, or just enjoy the panoramic views from above. The town’s charm is undeniable, and many travelers mention how well-preserved and atmospheric it remains. A highlight is the wine tasting at a local winery, where you’ll learn about the production process, from vineyard techniques to aging. The tasting includes multiple wines and local olive oil, making for a delicious and educational experience.

Wine Tasting and Final Reflection

The wine experience is a big part of this tour’s appeal. You’ll sample a selection of wines, learning how to appreciate their flavors while also understanding the craftsmanship behind them. Reviewers consistently mention the helpfulness and friendliness of guides at the wineries, making the tasting both fun and informative.

Return to Florence

After a full day of sightseeing, eating, and tasting, you’ll be comfortably transported back to Florence, ideally just in time for sunset. The tour’s timing and transportation mean you won’t have to worry about navigating public transport or rushing through the stops.

The Practical Side: What’s Included and What’s Not

The tour covers quite a bit, especially considering the price point of around $640 per person. Included in the package are:

• Professional guides in Siena and at the wineries
• Free time in each city, giving you the flexibility to explore or relax
• Luxury vehicle or premium van, ensuring comfort
• Lunch and wine tasting, a significant part of the experience
• Private tour, making it more intimate and tailored

However, it’s worth noting that hotel pickup and drop-off are not included. If you’re staying outside Florence city center, you’ll need to arrange your own transport to the meeting point at Cantinetta Antinori.

The Experience in Practice

Many reviewers highlight how seamless and personalized the tour is. For instance, one guest mentioned how their guide in Siena was extremely knowledgeable, making walking through the city effortless. Others appreciated the customized feel of the tour, with plenty of time for questions and exploration.

The small group size, especially with only your party or a few others, allows for a relaxed atmosphere. Some travelers even experienced the tour with just one other family, which they found very gratifying.

The Big Plus: The Guides and Wine

The guides received high praise across reviews. Comments like “Karim was amazing” and “Maria was very knowledgeable” show that the professionalism and friendliness of the guides really add to the experience.

Plus, the wine tasting was consistently described as a highlight, with many noting the quality of the wines and the informative session about winemaking. One reviewer said, “The wine and lunch was good,” which, while simple, captures how satisfying this part of the day can be.

What Could Be Better?

While the tour is largely praised, some might find the timing tight—an hour in Siena or San Gimignano is enough to get a taste but not to see everything in detail. Also, the price might seem steep for some, but considering the private, guided nature and inclusions, many feel it’s justified.

Who Should Consider This Tour?

This tour is perfect for those who want a relaxed yet comprehensive day exploring Tuscany’s highlights without the hassle of renting a car. It’s especially suited for travelers who value guided insights, good food, and local wines. The private setup makes it ideal for couples, families, or small groups who want an intimate experience.

It’s less suitable if you’re on a tight budget or if you prefer more independent, self-paced exploration. Also, if you’re traveling with children, keep in mind that some stops involve walking and sightseeing, so consider your group’s stamina.

Frequently Asked Questions

Is this tour suitable for children?
While there’s no minimum age requirement, children should be accompanied by an adult. The tour involves walking and sightseeing, so consider your kids’ stamina and interest level.

Does the tour include hotel pickup?
No, hotel pickup and drop-off are not included. You’ll need to meet at the designated starting point in Florence.

How long does the tour last?
The tour lasts approximately 9 hours and 30 minutes, starting at 8:00 am and returning in the late afternoon.

What’s included in the price?
Included are private transportation, guided tours in Siena and at the wineries, lunch, and wine tasting. It does not cover any personal expenses or optional activities outside the itinerary.

Can I customize the stops or itinerary?
Since it’s a private tour, there’s some flexibility, but the core stops and structure are predefined. Any custom requests should be discussed ahead of time.

How many people can join?
A maximum of 8 people per booking ensures a comfortable, intimate experience.

Is there any age restriction?
No minimum age is specified, and children are welcome with adult supervision.

What is the cost per person?
It’s approximately $640.41 per person, reflecting the private, guided nature of the experience.

Wrapping It Up

For lovers of history, scenery, and wine, this private tour from Florence offers a well-rounded day immersed in Tuscany’s charms. The combination of guided insight, free exploration time, and culinary delights creates a balanced experience suitable for many travelers.

The attention to detail, the quality of guides, and the inclusion of a wine tasting make it a good value for those looking to indulge a little while discovering some of Italy’s most iconic towns. While it’s pricier than some group options, the personalized touch and comfort level are often highlighted as worth it.

If your goal is a relaxed, authentic taste of Tuscany—without the stress of driving or rigid schedules—this tour could be just what you need. It’s particularly ideal for those who value expert guidance and a bit of luxury in their travel adventures.

Let me know if you want additional tips or alternative options, but overall, this tour seems like a solid choice for a memorable Tuscan day out.