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Experience Tuscany's beauty on a private full-day tour from Florence, visiting Montepulciano, Pienza, and two boutique wineries with tastings and authentic lunch.

This exclusive Val d’Orcia tour from Florence offers a full-day adventure into the heart of Tuscany’s UNESCO World Heritage site for $609.62 per person. With 12 hours of guided exploration, it provides a seamless way to visit the picturesque towns of Montepulciano and Pienza, plus two boutique wineries, all with the comfort of private transportation and a dedicated guide. The tour features wine tastings, a local farm-to-table lunch, and free time in iconic towns, making it ideal for those who want an immersive experience without the hassle of planning.
While the group size is limited to your private party, the tour is designed to accommodate those interested in Tuscan culture, wine, and scenic views. It’s perfect for travelers who appreciate expert-guided visits and authentic local cuisine, with the flexibility that a private driver offers. A key note: this tour departs early at 7:30 am and requires booking 9 days in advance on average, so planning ahead is essential.

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The day begins with a pickup from your Florence accommodation at 7:30 am. The private driver arrives typically around 7:15 am to ensure an on-time departure. The drive to the first winery takes approximately 1 hour and 45 minutes, setting the tone for a comfortable, no-stress day of exploration. The tour ends back in Florence, with a drop-off at your original pickup point or another location with prior notice. The return trip typically takes about 15 minutes.
This logistical setup allows travelers to relax and enjoy the scenery from the start, without worrying about navigation or large group movements. The private nature of the tour means you can customize your experience slightly if needed, and the certified sommelier guide ensures insightful commentary throughout the day.

The first stop is Montepulciano, a medieval town perched atop a hill in southern Tuscany. Known for its Renaissance architecture and historic charm, Montepulciano offers a stroll through narrow cobblestone streets lined with elegant buildings. The town is a must-see destination for its panoramic views over the surrounding countryside and its famous Vino Nobile di Montepulciano.
Visitors enjoy free time to explore at their own pace, taking in sights like Piazza Grande and the cathedral, or simply relaxing at a local café. The one-hour visit provides enough opportunity to get a sense of the town’s atmosphere without feeling rushed, making it ideal for history buffs and architecture lovers alike.

The first winery visit takes place at Azienda Agricola Ercolani, located underground of Montepulciano. This unique cellar complex features Etruscan tombs, ancient wells, and cellars where Ghibellines once hid, creating a surprisingly historic atmosphere beneath the town.
The family-run estate is passionate about art and history, which is reflected in their recreated small museums. Visitors encounter oak barrels of various sizes, and can explore the traditional underground passages. This 1 hour 30 minutes tour includes a wine tasting of one of Tuscany’s most important wines, offering insights into the region’s winemaking traditions. The admission is included in the tour fee, making this a rich experience for oenophiles and history enthusiasts alike.

Next, the tour moves to Tenuta Fanti, a historic estate since 1800 that has transformed from sharecropping to a modern organic winery. The estate sprawls over 260 hectares, with 55 hectares of vineyards, 60 hectares of olive trees, and 145 hectares of crops and forest.
The volcanic soil and skeleton-rich terrain give Fanti wines a distinctive character. The winery’s conversion to organic practices reflects a commitment to sustainability and quality. The guided tour of the state-of-the-art facilities offers insights into their philosophy and production process, culminating in a wine tasting session that showcases their best offerings. This experience lasts about 3 hours and is included in the overall tour price.
Following the winery visits, the tour stops at Pienza, renowned as the “touchstone of Renaissance urbanism”. This medieval town is situated between Montepulciano and Montalcino, and features well-preserved architecture and breathtaking views of the Tuscan landscape.
The one-hour visit allows ample opportunity to explore Pienza’s historic streets, admire its Renaissance buildings, and take in the scenic vistas. The town’s compact size makes it ideal for a relaxed walk, with plenty of photo opportunities and local shops to browse. The stop provides a perfect balance of culture and leisure.

A highlight of this tour is the farm-to-table lunch served near Pienza. The meal features local Tuscan dishes prepared with fresh, locally sourced ingredients from the estate’s own organic farms and nearby producers. This traditional meal emphasizes the region’s culinary heritage and offers a genuine taste of Tuscany.
The lunch provides time for relaxation and socialising, with the opportunity to enjoy regional specialties in a rustic yet comfortable setting. The emphasis on 0 km products ensures freshness and supports local agriculture, making this meal both delicious and sustainable.

The entire day is conducted as a private experience, with only your group participating. The certified sommelier guide leads the way, providing insightful commentary on wine, history, and local culture. The private transportation allows for flexible timing, so you can customize your stops or extend your stay in places that interest you most.
This personalized approach ensures a relaxed pace and the opportunity to ask questions, making the experience especially suitable for those who prefer more intimate and tailored tours. The free time in Montepulciano and Pienza is a significant advantage, allowing you to deepen your exploration at your own pace.
The tour begins at 7:30 am with a pickup in Florence, and the entire experience lasts approximately 12 hours. Booking typically occurs 9 days in advance, highlighting the need for early planning. The tour includes pickup from your accommodation, private transport, visits to 2 boutique wineries, wine tastings, a traditional lunch, and guided sightseeing.
Cancellation is free up to 24 hours before the scheduled start, providing peace of mind in case of change of plans. The tour requires good weather, and if canceled due to poor conditions, a full refund or rescheduling is offered.
This full-day private tour is best suited for travelers seeking an in-depth, comfortable experience of Tuscany’s wine, towns, and landscapes. It appeals particularly to those who value guided insights, local cuisine, and flexible free time. Wine enthusiasts will appreciate the tastings at two boutique wineries, and history lovers will enjoy exploring Montepulciano and Pienza.
Since the tour is fully private, it is a good choice for couples, families, or small groups wanting a personalized day in Tuscany. It’s less suitable for those on a tight budget or with limited mobility, given the walking involved in town visits and some uneven terrain at the wineries.
Compared to similar experiences, this private Val d’Orcia tour from Florence offers customized visits, exclusive winery tours, and a focus on local organic products, all with the comfort of private transport. The knowledgeable guide enhances the experience with deep insights into wine and history, making it more than just a sightseeing trip.
The early start and comprehensive itinerary ensure you cover the key highlights of the region in a single day, making it an efficient yet relaxing option. The highly positive reviews underscore its quality, especially for wine lovers and those wanting an intimate look at Tuscany’s cultural treasures.
“The highlight of our honeymoon was our private tour with Angel! He was knowledgeable, easygoing, and planned everything impeccably. He also gave us…”
Is this tour suitable for children?
Children must be accompanied by an adult. The minimum drinking age is 18, so wine tastings are only for adults.
What is included in the tour price?
The price covers visits to 2 boutique wineries, wine tastings, a local farm-to-table lunch, private transportation, and a certified sommelier guide.
Can I cancel the tour?
Yes, free cancellation is available up to 24 hours before the tour start. Full refunds are issued if canceled within this window.
What is the duration of the entire tour?
The tour lasts approximately 12 hours, starting early in the morning and returning in the evening.
Are the winery tours and tastings included?
Yes, both winery tours and tastings are included as part of the experience.
Is this a group or private experience?
It is a completely private tour, with only your group participating, providing a personalized and relaxed atmosphere.
Are dietary restrictions accommodated?
Yes, if you have special dietary requirements, please inform the provider in advance.
What should I wear or bring?
Comfortable walking shoes are recommended for town exploration. No specific dress code is required for the winery visits or lunch.
What makes this tour unique compared to others?
The private experience with exclusive winery visits, organic lunch, and the flexibility to enjoy free time in Montepulciano and Pienza distinguish this tour from larger group options.
How do I book this tour?
Booking is best done 9 days in advance, and you can confirm your spot through the provided platform or contact Enotropea Tours directly.
This Val d’Orcia private tour from Florence offers a well-rounded look at Tuscany’s wine, towns, and landscapes, combining comfort, expert guidance, and local flavors. It’s an excellent choice for those seeking a luxurious, personalized day in Italy’s most scenic region.