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Explore Tuscany’s UNESCO-listed Val d'Orcia in a private, wine-tasting tour from Florence, visiting Montepulciano and Pienza with expert guides and organic farm lunches.
Our review of the Exclusive Val d’Orcia Tour from Florence paints a picture of a thoughtfully curated experience that combines scenic beauty, historical charm, and authentic Tuscan flavors. Perfect for couples, friends, or anyone craving a more personal look at Tuscany’s famed landscape, this tour offers a private driver, expert-guided visits, and a chance to indulge in local wines and farm-to-table cuisine.
What we love most about this experience is the combination of luxury and authenticity—you’re not just rushing through tourist spots but savoring the region at a relaxed pace, with tailored insights from a knowledgeable guide. The tour’s highlight is visiting two boutique wineries, with exclusive tours and tastings that reveal the craftsmanship behind some of Tuscany’s finest wines.
One potential consideration is the lengthy day, roughly 12 hours, which can be tiring for some. Still, if you’re eager to soak in the Tuscan countryside without the hassle of public transport, this private tour is a superb choice. It’s especially well-suited for travelers who enjoy wine, history, and scenic drives in comfort and style.
This experience is best for those seeking a personalized, luxury day out, eager to explore Tuscany’s beauty at their own pace, and interested in authentic wine tastings and regional cuisine. It’s ideal for couples, small groups, or anyone wanting a curated, memorable day in the Val d’Orcia.

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Starting the day at 7:30 am, you’ll be picked up from your Florence accommodation—early enough to make the most of your day but not so early that you’ll feel rushed. With a private driver, the roughly 1 hour 45-minute drive to Montepulciano flies by, with scenic views of rolling hills and vineyards. Having your own vehicle means you can relax, enjoy the landscape, and avoid the chaos of group transport.
Your first stop, Montepulciano, is a medieval jewel perched atop a hill in southern Tuscany. Here, wandering through its Renaissance streets feels like stepping back in time. From the impressive town walls to the elegant architecture, you’ll see why this town has been a favorite for centuries. Reviewers mention that guides excel at sharing local stories, making the visit both educational and enjoyable.
You’ll have about an hour to explore, take photos, and soak in the atmosphere. One reviewer notes, “Angel, our guide, was knowledgeable and easygoing, giving us just enough time to enjoy the town on our own.” It’s a chance to browse charming shops, admire the views, or just sit at a café and sip some local wine or coffee.
Next, you descend into the underground cellars of Azienda Agricola Ercolani, where the real magic of Tuscan winemaking unfolds. The family has infused this tour with history, art, and tradition—encountering oak barrels, authentic Etruscan tombs, and ancient wells along the way. The guide, well-versed in local lore, points out details like the Ghibellines’ refuge and the coins tossed into wells for good luck.
The highlight is the wine tasting inside these historic cellars, giving you a taste of some of Tuscany’s most renowned wines. Reviewers praise the guide’s knowledge, with one saying, “They took the time to explain the traditions behind each wine, making the tasting so much more meaningful.” This stop typically lasts around 1 hour 30 minutes, allowing plenty of time to savor the wines and appreciate the setting.
Afterwards, you’ll visit Tenuta Fanti, a family-run estate dating back to 1800, now committed to organic practices. The estate spreads over 260 hectares, with vineyards, olive groves, and forests, all of which contribute to their wine and olive oil production.
The guided tour here explains their philosophy of organic cultivation and respect for the land. The estate’s volcanic soil lends a distinctive character to their products. The lunch served on the estate is a major highlight: a traditional Tuscan meal featuring local ingredients, prepared with a farm-to-table approach. Many reviews emphasize how delicious and authentic the food was—an ideal pairing with the wines tasted earlier.
Post-lunch, you’ll have about an hour to explore Pienza, known as the “touchstone of Renaissance urbanism.” Its compact, well-preserved streets offer breathtaking views and quaint shops. Similarly, the time in Montepulciano allows for a relaxed stroll or a quick coffee, depending on your mood.
One reviewer loved the chance to wander freely: “It was nice having time on our own to sit at a piazza and just take it all in.” This flexibility is a major perk, allowing you to tailor the experience slightly to your interests.
Your guide will return you to your Florence accommodation, usually within 15 minutes of the scheduled time. The long day may leave you tired but truly satisfied, having experienced Tuscany in a way few do—private, intimate, and full of flavor.

When considering the price of approximately $609.62 per person, think about what’s included: private transport, expert guides, two boutique wineries, tastings, and a farm-to-table lunch. This all adds significant value, especially given the exclusive access and personalized attention. Compared to other group tours, this private experience offers more flexibility, comfort, and a chance to connect deeply with the region.
Authentic experiences like the underground cellar tour and organic farm visit are often unavailable on larger, more generic trips. The reviews underscore the value, with one guest remarking, “Angel made our honeymoon unforgettable with his knowledge and relaxed style.”
Timing is well-paced, allowing you to enjoy each stop without feeling rushed. The early pickup is perfect for maximizing daylight hours, and the private driver means you can enjoy the scenery without stress.
Most travelers find the duration manageable, especially if you’re fond of wine and history. The tour’s exclusivity and intimate nature make it ideal for those wanting a special, personalized day out, rather than a rushed, crowded experience.

Wine lovers: The two wine tastings, especially at boutique wineries, are the main attraction.
History and architecture fans: The towns of Montepulciano and Pienza offer stunning Renaissance architecture and medieval charm.
Food enthusiasts: The farm-to-table lunch emphasizes local, organic ingredients, showcasing Tuscan culinary traditions.
Travelers seeking comfort and flexibility: The private driver and personalized itinerary are perfect for those who prefer a relaxed, tailored experience.
Couples or small groups: The intimate setting and personalized guiding make it ideal for celebrating special occasions or simply enjoying quality time.

This private Val d’Orcia tour from Florence strikes an excellent balance between comfort, authenticity, and exclusivity. You get to explore some of Tuscany’s most picturesque towns with the guidance of knowledgeable locals, sample exquisite wines, and enjoy a delicious regional lunch—all without the hassles of public transport or large groups.
The attention to detail, from the underground winery tour to the organic estate visit, creates a layered experience that resonates with those truly eager to understand and appreciate Tuscany’s wine, culture, and landscape. While the day is long, many reviewers mention that the seamless planning and expert guide make it feel effortless and enriching.
If you’re looking for a meaningful, stress-free way to experience Tuscany’s charm, this tour offers an excellent value—especially if you prioritize personalized service and authentic regional highlights.

What time does the tour start?
Pickup typically begins at 7:30 am from your Florence accommodation, with the driver arriving around 7:15 am.
Is this a group or private experience?
It’s a completely private tour for your group only, offering personalized attention and flexibility.
How long is the tour?
The entire experience lasts approximately 12 hours, making it a full day of sightseeing and tasting.
Are meals included?
Yes, you’ll enjoy a farm-to-table lunch featuring local Tuscan dishes, made with ingredients sourced from nearby farms.
Which towns will I visit?
You will explore Montepulciano, Pienza, and visit two wineries in the region.
Are there wine tastings?
Absolutely. You’ll visit two boutique wineries—Azienda Agricola Ercolani and Tenuta Fanti—with guided tours and tastings included.
Can I customize the itinerary?
While the core stops are fixed, the private nature of the tour offers some flexibility, especially in free time in towns.
Is there a dress code?
Smart casual is suitable—comfortable shoes are recommended for walking around towns and wineries.
Can children join?
Children are welcome but must be accompanied by an adult. The minimum drinking age is 18.
In sum, this private Val d’Orcia tour offers a well-rounded, luxurious look at Tuscany’s landscape, towns, and wines, making it a top choice for those who want a memorable, personalized day in Italy’s most photographed region.