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Discover Tuscany’s iconic wines on a private 9.5-hour tour from Florence, visiting Montalcino and Montepulciano with wine tastings, underground cellars, and scenic views.


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The tour begins at 8:30 AM at Piazza Adua, just in front of Santa Maria Novella Station. A local driver-guide takes you southward through Tuscany’s rolling hills, making the journey as scenic as the destinations themselves.
Traveling in a private group, you have the comfort and flexibility to enjoy the countryside at a relaxed pace. The drive lasts approximately 1 hour and 50 minutes, setting the stage for a full day of wine, history, and breathtaking views.
Arriving in Montalcino, known worldwide for Brunello di Montalcino, you get 40 minutes to explore its historic center. The guided walk with the guide reveals insights into the town’s history, traditions, and wine-making culture that have elevated Brunello to international fame.
A short drive of about 5 minutes takes you to a local winery. Here, you indulge in a Tuscan lunch with wine tastings, enjoying a selection of Brunello di Montalcino wines. The meal features local specialties such as crostini, cured meats, cheeses, and a typical Tuscan dessert, all matched with the estate’s wines.
Post-lunch, the tour continues to Montepulciano, a historic town celebrated for its Vino Nobile di Montepulciano. You have 40 minutes to wander through the charming streets, soaking up its medieval and Renaissance architecture.
Next, a guided visit takes you underground to cellars and historic wineries. Here, you taste Vino Nobile di Montepulciano, including a Gran Riserva, gaining understanding of its production process and aging. This small-group experience emphasizes the craftsmanship behind these celebrated wines.
More Great Tours NearbyBetween the two towns, the trip offers breathtaking vistas of Val d’Orcia, a UNESCO World Heritage Site. The landscape is famous for its rolling hills, cypress trees, and cinematic scenery featured in films like Gladiator.
This drive provides plenty of photo opportunities and a chance to appreciate Tuscany’s agricultural beauty and timeless scenery.
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On the return journey to Florence, the tour pauses at Piazzale Michelangelo around 6:00 PM. From this vantage point, travelers enjoy a panoramic view of Florence and a perfect setting for an aperitivo.
It’s a relaxed moment to toast the day and reflect on the wines, towns, and scenery encountered during this exceptional tour.
This private group experience ensures personalized attention from the guide. The tour includes flexible timings, with full cancellation available up to 24 hours in advance and the option to reserve now and pay later.
The meeting point is conveniently located at Adua Square, making it easy to access from Florence’s main train station. The total duration is 9.5 hours, making it a comprehensive yet manageable day trip.
What makes this tour particularly appealing is its dedication to premium wines like Brunello and Vino Nobile, along with the opportunity to visit underground cellars and taste wines directly from the producer. The scenic drive through Val d’Orcia enhances the experience beyond just wine, offering stunning vistas and a sense of Tuscany’s landscape.
The quality of guides and the attention to detail in the tastings and meals contribute to its high 4.8 rating from past participants. It’s ideal for wine enthusiasts and travelers seeking a luxurious, in-depth exploration of Tuscany’s wine towns.
The tour’s physical demands are moderate—mainly walking through historic centers and some stairs in underground cellars. The private setting minimizes crowds, making it suitable for those who prefer a more intimate experience.
Since the tour is language-friendly in English, Spanish, and Italian, it caters to a wide audience. It’s a full-day experience, so comfortable shoes and a camera are recommended to capture the views and architecture.

Both towns offer unique charms. Montalcino is best known for its prestigious Brunello wines and medieval fortress, while Montepulciano charms with its medieval streets and Vino Nobile wines. The guided visits and tastings at wineries let you taste wines in their authentic production environments.
The Tuscan lunch includes local specialties carefully matched with wines, providing a genuine taste of regional cuisine. The crostini, cured meats, cheeses, and desserts complement the wine tastings and make for a satisfying meal.
The Val d’Orcia drive showcases Tuscany’s most picturesque landscapes, often seen in movies and travel magazines. The Piazzale Michelangelo visit in Florence caps the day with a breathtaking view of the city and a chance to relax with an aperitivo.

This private tour from Florence offers an engaging combination of wine tastings, historic explorations, and magnificent scenery. It excels in providing a personalized experience with knowledgeable guides, making it ideal for those who want to dive deep into Tuscany’s wine culture.
While the day involves walking and some steps in underground cellars, the scenic drives and luxury tastings compensate for any physical demands. The flexibility and high rating from past participants make it a top choice for wine lovers and culture seekers alike.
This tour suits travelers who appreciate premium wines, scenic drives, and authentic Tuscan towns. It offers a well-rounded experience packed with insights, flavors, and stunning views—a true celebration of Tuscany’s wine heritage.

Is the tour suitable for children or non-drinkers?
Since the focus is on wine tastings and visits, it’s primarily designed for adults. However, the scenic drives and sightseeing may appeal to non-drinkers, but check with the provider for specific policies.
Are meals included in the tour?
Yes, a Tuscan winery lunch with local specialties and wine pairings is part of the experience, giving a flavorful taste of regional cuisine.
How do I meet the guide in Florence?
The meeting point is Piazza Adua, just in front of Santa Maria Novella Station, next to the Burger King.
Can I cancel my booking?
Yes, the tour offers full cancellation up to 24 hours in advance with a full refund.
What languages are available for the guide?
The tour is conducted in English, Spanish, and Italian, providing options for diverse travelers.