From Florence: PRIVATE Siena and San Gimignano with wine tasting

Explore Tuscany’s Historic Towns with a Private Full-Day Tour from Florence

This private tour from Florence offers a seamless way to experience Siena, San Gimignano, and Monteriggioni without the hassle of driving or planning logistics. Priced at $640.41 per person, the tour lasts approximately 9 hours and 30 minutes, making it an ideal full-day escape. Led by an English-speaking guide, the tour combines cultural highlights, historic sites, and authentic Tuscan flavors.

What makes this tour particularly appealing is its focus on free time in each location, allowing travelers to explore at their own pace. The included gourmet lunch and guided wine tasting add extra depth to the experience. While the tour is best suited for those comfortable with moderate walking and outdoor exploration, it offers a well-rounded taste of Tuscany’s iconic towns and countryside.

Key Points

• Private full-day experience with round-trip transportation from Florence
• Visits Siena, San Gimignano, and Monteriggioni with free exploration time
• Includes a gourmet Tuscan lunch and guided wine tasting
• Tour duration of approximately 9.5 hours with comfortable air-conditioned minivan
• Small group size with a maximum of 8 guests for a personalized experience
• No hotel pickup or drop-off, meeting at Piazza degli Antinori

Comfortable and Convenient Transportation in a Premium Minivan

The tour begins at 8:00 am from Piazza degli Antinori in Florence, where travelers meet at the Cantinetta Antinori. A luxury or premium van with air conditioning and free water awaits, driven by an English-speaking driver. This setup ensures a smooth, comfortable ride throughout the day while the driver provides helpful explanations about the route and surroundings.

This transportation arrangement is ideal for those who prefer to avoid public transit or renting a car. The small group size guarantees personalized attention, and the full-day transfer minimizes fatigue, allowing travelers to focus on sightseeing and tasting.

Discover Siena’s Medieval Charm with a Local Guide

In Siena, a local guide leads a one-hour walking tour through the city’s most iconic spots. The focus is on Piazza del Campo and Piazza del Duomo, where the authentic medieval atmosphere is palpable. Visitors appreciate the knowledgeable guide for their storytelling about Siena’s history and architecture.

Following the guided portion, travelers enjoy one hour of free time. This is perfect for visiting the Siena Cathedral, shopping for local products, or simply soaking in the unique ambiance of this historic town. Admission to the cathedral is not included, but the guided walk offers a rundown of Siena’s highlights.

Monteriggioni’s Fortress and Tuscan Lunch Experience

Next stop is Castello Monteriggioni, a walled medieval town built in 1213. Its round enclosure is famously referenced by Dante Alighieri in the Divine Comedy, making it a significant historical site. The town’s well-preserved ramparts and towers provide a striking backdrop for photos and exploration.

Here, travelers enjoy a lunch and local wine in a beautiful setting, included as part of the tour. The 1 hour and 30 minutes spent at Monteriggioni allow ample time to relax, sample regional cuisine, and appreciate the scenic views of Tuscany’s rolling hills.

Scenic Drive Through Chianti’s Vineyards to San Gimignano

The route from Monteriggioni to San Gimignano takes travelers along Chianti’s picturesque landscape, featuring vineyards and olive groves. This scenic drive offers a perfect setting for appreciating Tuscany’s countryside charm.

Once in San Gimignano, travelers have one hour and 30 minutes of free time to explore “The City of Towers”. Recognized as a UNESCO World Heritage site, San Gimignano impresses with its medieval skyline of towers and narrow streets. It’s a favorite for those wanting to experience authentic Italian medieval architecture.

Wine Tasting in San Gimignano’s Local Winery

In the afternoon, the tour includes a guided wine tasting at a local winery. Visitors learn about vineyard techniques, the wine-making process, and aging methods. They also discover how to appreciate different wines and local olive oils. The tasting session lasts approximately 1 hour and 15 minutes and is free of charge.

This hands-on experience offers insights into Tuscan wine culture and complements the sightseeing, making it ideal for wine enthusiasts or those curious about regional flavors.

Return to Florence with Sunset Views

After the wine tasting, the group boards the minivan for the return trip to Florence, arriving just in time for sunset. The comfortable transport ensures a relaxed end to the day, with the chance to reflect on a full day of exploration and tasting.

The tour concludes at the meeting point in Florence, with no included hotel transfer, making it best suited for travelers staying near central Florence or those prepared to arrange their own transportation afterward.

Unique Aspects and Notable Features of the Tour

This private Tuscany day trip distinguishes itself through its balance of guided and free exploration, inclusive lunches and tastings, and luxury transport. The small group size enhances the personal experience, and the local guides are praised for their knowledge and engaging storytelling.

The flexibility in free time allows visitors to tailor their experience at each stop — whether visiting museums, shopping, or simply wandering the streets. The wine tasting adds a sensory layer, deepening the appreciation of the region’s renowned products.

Practical Considerations and Limitations

While the tour offers a rundown, it does not include hotel pickup or drop-off, requiring guests to meet at the designated location in Florence. The minimum booking size is 2 people, and the maximum is 8, making it well-suited for intimate groups or family outings.

Travelers should be prepared for moderate walking, especially in Siena and San Gimignano, and should plan accordingly if they have mobility concerns. The 9.5-hour duration means a full day of activity, so packing comfortable shoes and some cash for additional purchases is advisable.

Who Will Enjoy This Tour Most?

This tour appeals most to culture and history enthusiasts, wine lovers, and those seeking a stress-free way to see multiple towns in a single day. It’s especially good for small groups or families looking for a personalized experience with guided insights and local flavors.

Travelers who want flexibility in exploring each town at their own pace will appreciate the free time, while those interested in Tuscan cuisine and wine will find the included lunch and tastings particularly rewarding.

Final Thoughts on the Tuscany Private Day Trip from Florence

This well-rounded tour offers a taste of Tuscany’s historic towns, scenic landscape, and regional wines all in one day. The private setup with luxury transportation and personal guides makes it a comfortable and informative choice. While it requires some planning for logistics beyond the meet-up point, the experience is tailored for those who want depth without the hassle.

Ideal for families, couples, and small groups, this tour delivers a balanced mix of sightseeing, culture, and culinary delights. The high ratings and positive reviews underscore its popularity and quality, making it a reliable option for an immersive Tuscan experience.

Frequently Asked Questions

Is hotel pickup included in this tour?
No, the tour begins at the designated meeting point in Florence, Piazza degli Antinori.

What is the best time of day to join this tour?
The tour departs at 8:00 am, providing a full day to explore Siena, Monteriggioni, and San Gimignano with time for tasting and sightseeing.

How long is the overall tour?
The entire experience lasts approximately 9 hours and 30 minutes, including travel, guided tours, free time, lunch, and wine tasting.

Are children allowed on this tour?
Yes, there is no minimum age required, but children must be accompanied by an adult.

What is included in the price?
The price covers round-trip transportation, a local guide in Siena, lunch, guided wine tasting, and admission tickets to Monteriggioni and San Gimignano.

Can I cancel this tour?
Yes, there is free cancellation up to 24 hours before the start, with a full refund.

What should I bring for the wine tasting?
While the tasting is included, bringing a small cash or card for additional purchases or souvenirs is recommended.

Is this tour suitable for those with mobility issues?
There is some walking involved at Siena and San Gimignano, so travelers with mobility concerns should consider this before booking.