From Florence: PRIVATE Siena and San Gimignano with wine tasting

Exploring Tuscany: A Private Day Trip from Florence to Siena, San Gimignano, and More

This private tour from Florence promises a full day of authentic Tuscan sights, flavors, and history — without the hassle of driving. With a knowledgeable guide at your side and all transportation taken care of, it’s designed to maximize your Italian adventure. From the striking striped cathedral in Siena to the medieval towers of San Gimignano, each stop offers a unique glimpse into Tuscany’s charm.

What truly makes this experience stand out is the combination of guided visits, ample free time, and delicious local indulgences — especially the wine tasting and gourmet lunch. It’s a thoughtfully crafted itinerary that balances structured exploration with relaxed moments to soak in the scenery and culture.

However, a potential consideration is that this tour is quite comprehensive, so you’ll want to pace yourself and be prepared for a long day. Also, as a private experience, it’s better suited for travelers who appreciate a more personalized, flexible approach rather than large group tours. This is ideal for those seeking an authentic, immersive day in Tuscany with a slice of luxury.

Key Points

• Customizable private experience: Tailored to your group with a dedicated guide and driver.
• Visit iconic Tuscan towns: Siena, San Gimignano, and Monteriggioni, each bursting with history and character.
• Includes a local gourmet lunch and wine tasting: A true taste of Tuscany’s culinary delights.
• Ample free time in each location: Perfect for exploring at your own pace and discovering hidden corners.
• Comfortable transportation: Air-conditioned minivan ensures a relaxed journey between stops.
• Ideal for those wanting an immersive, flexible day trip from Florence.

The Itinerary: A Deep Dive

Starting Point and Transportation

Your day begins at the Piazza degli Antinori in Florence, where you’ll meet your private guide and driver. The journey to Tuscany is made in a luxury, air-conditioned minivan, designed for comfort and quiet so you can relax and enjoy the views of rolling vineyards and olive groves. Water is provided, helping you stay refreshed during the approximately 9-and-a-half-hour itinerary.

First Stop: Siena

Arriving in Siena, a local guide will meet your group and lead you through some of the town’s most atmospheric sites. Expect to wander around Piazza del Campo, famous for its shell shape and medieval architecture, and the nearby Piazza del Duomo with its impressive cathedral. One reviewer described Siena as having an “authentic medieval atmosphere” that makes it a striking and memorable stop. The guided tour lasts about an hour, giving you a solid introduction to Siena’s history and layout.

Afterward, you’ll have roughly an hour of free time. This is a great chance to explore at your own pace — whether to visit the cathedral (admission included in some tours, though not explicitly here), shop for local crafts, or simply enjoy a gelato while soaking in the lively streets.

Lunch and Monteriggioni

Back into the van, your next destination is Monteriggioni, a small but famously fortified hilltop town built in 1213. Its walls are so well-preserved that Dante Alighieri references it in the Divine Comedy. Travelers have appreciated the opportunity to explore this medieval fortress, with one reviewer noting how much time they spent here, especially kids who loved wandering the ramparts.

A highlight here is the gourmet Tuscan lunch, included in the tour, served in a scenic setting that complements the town’s fairy-tale feel. The meal includes local wine, offering a true taste of regional flavors. The lunch lasts about an hour and a half, providing time to relax and enjoy the company.

San Gimignano: The Towered Town

Driving through the Chianti landscape, filled with vineyards and olive groves, you’ll arrive at San Gimignano, often called the “Medieval Manhattan” because of its skyline of towers. UNESCO has designated it a World Heritage site, thanks to its well-preserved architecture.

Guests are free to wander for about 90 minutes, exploring the narrow streets, boutique shops, and panoramic viewpoints. One reviewer mentioned how easy it was to walk through the town with the help of their guide Anna, who was praised for her knowledge and friendly manner. It’s a picturesque spot that offers plenty of photo opportunities and a chance to absorb the medieval atmosphere.

Wine Tasting in San Gimignano

Concluding your sightseeing, you’ll visit a local winery for a guided wine tasting. Expect to learn about the winemaking process — from vineyard techniques to aging — and how to appreciate different wines. You’ll also get a chance to taste local olive oils, a perfect way to savor the flavors of Tuscany. One reviewer highlighted how enjoyable and educational this part of the tour was, emphasizing the quality of the wines and the friendly, knowledgeable guide.

Return to Florence

After a full day of sightseeing, tasting, and exploring, your guide will escort you back to Florence, arriving just in time to catch the sunset. The comfortable van makes the return journey relaxing, allowing you to reflect on a day packed with culture, history, and culinary delights.

What Makes This Tour Special?

This private experience offers a level of personalization and flexibility that larger group tours often lack. You’ll appreciate the customized guided walks and the ability to spend as much or as little time as you wish at each stop. The inclusion of lunch and wine tasting adds value, transforming a sightseeing day into a true culinary journey.

Reviewers have consistently praised the guides for their knowledge and friendliness. One noted how helpful Luca, the driver, was, explaining everything smoothly while driving through the scenic landscape. Another highlighted Maria, Siena’s local guide, as being very knowledgeable and engaging, making the history come alive.

The price point of around $640 per person might seem steep to some, but considering the private nature, gourmet meal, and wine tasting, many feel it offers excellent value. It’s especially ideal for couples, families, or small groups who want a tailored, memorable experience without the stress of navigating themselves.

Practical Considerations

Since the tour is private, the group size is limited to a maximum of 8 people, ensuring a more intimate setting. The tour departs at 8 am, giving you plenty of time to enjoy the day. Keep in mind, hotel pickup and drop-off are not included, so you’ll need to meet at the designated starting point or arrange your transportation.

The tour runs rain or shine, and confirmation is immediate, so you can plan confidently. It’s suitable for most travelers, with no minimum age requirement, making it a versatile choice for families, couples, or friends.

Final Thoughts: Is It Worth It?

This tour ticks many boxes for those wanting an immersive, flexible, and well-rounded day in Tuscany. The combination of guided visits, free exploration time, and regional tastings offers a balance that few group excursions can match. If you love discovering historic towns, savoring local wines, and enjoying authentic food in scenic settings, this experience will likely meet or exceed your expectations.

It’s especially well-suited for travelers seeking a luxurious, personalized trip with knowledgeable guides and seamless transportation. The inclusion of a gourmet lunch and wine tasting elevates the experience from simple sightseeing to a memorable culinary adventure.

However, if you prefer to explore independently or have limited time, this organized approach saves you the hassle of planning logistics and navigating public transport. Just be prepared for a full day, and bring comfortable shoes and an appetite for Tuscan delights.

Frequently Asked Questions

Is this a private tour?
Yes, this experience is exclusively for your group, providing a personalized and flexible itinerary.

What is included in the price?
The tour includes private transportation in a luxury van, guided visits in Siena, a Tuscan lunch with local wine, and a guided wine tasting. It does not include hotel pickup or drop-off.

How long does the tour last?
The entire experience lasts approximately 9 hours and 30 minutes, from the meeting point in Florence to returning.

What stops are part of the itinerary?
You’ll visit Siena (with guided tour and free time), Monteriggioni (with lunch), San Gimignano (free exploration), and enjoy a wine tasting at a local winery.

Is there any age restriction?
No, there’s no minimum age requirement. Children must be accompanied by an adult, making it suitable for families.

What should I wear?
Comfortable shoes and layered clothing are recommended, as you’ll be walking in historic towns and possibly outdoors.

Can I customize the experience?
Since it’s a private tour, you can discuss your preferences with the guide beforehand, making adjustments as needed.

Is lunch included?
Yes, a traditional Tuscan lunch with wine is part of the package, served in Monteriggioni.

What is the cancellation policy?
You can cancel for free up to 24 hours in advance. Cancellations later than that are not eligible for a refund.

This private Tuscan tour from Florence offers a thoughtfully curated, authentic experience that balances sightseeing, tasting, and culture. It’s a fantastic choice for those wanting to explore Tuscany’s highlights in comfort and style, with plenty of opportunities to personalize your day.