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Discover Tuscany with a full-day wine tasting in Montepulciano and charming visits to Pienza and Montepulciano town, starting from Rome for $517.90 per person.
Exploring Tuscany on a day trip from Rome offers a perfect blend of scenic landscapes, historic towns, and authentic wine tasting experiences. This 10-hour private tour costs $517.90 per person and promises visits to Montepulciano’s vineyards, the medieval town of Montepulciano, and the picturesque Pienza. The tour includes luxury transportation with WiFi, a guided winery tour, and tastings of DOCG wines, such as Nobile di Montepulciano and Vin Santo. While the tour is generally praised for its stunning views and expert guides, some reviews note that English fluency from the driver may vary, and the overall value depends on individual expectations.
This tour suits lovers of wine, history, and beautiful scenery who are comfortable with a full day of sightseeing. It features small-group private transportation and visits to local farms, making it an immersive taste of Tuscany’s culinary and cultural riches. It’s important to plan for limited free time at some stops and prepare for a busy itinerary, but the overall experience remains memorable for those wanting a comprehensive introduction to this iconic region.


The tour departs from Rome early in the morning, with a luxury car and an English-Spanish speaking driver. The journey into Tuscany takes you through the famous Crete Senese, characterized by clay hills and lush landscapes. Expect splendid panoramic views of the green hills and vineyard-covered slopes that make this region so visually captivating. The drive itself is a highlight, setting the tone for a day immersed in Tuscany’s natural beauty.
The comfortable transportation, equipped with WiFi, allows for a relaxed start, where travelers can enjoy the scenery and ask questions about the local landscape. The pacing of the drive is considered suitable for a full-day trip, with enough time allocated for each stop to appreciate the surroundings.
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The first main stop is at a prestigious local farm in Montepulciano, where a guided winery tour is led by a wine expert. The winery, located on an estate with splendid vineyards and cellars, offers an in-depth look at local wine production. Visitors can taste up to 5 organic wines, with the winemaker Alfredo sharing stories of wine’s history and explaining tasting techniques.
The tasting includes Nobile di Montepulciano, a renowned DOCG wine, along with other local and fruity varieties, plus Vin Santo, a sweet Tuscany dessert wine. The experience emphasizes genuine, natural products like extra virgin olive oil and cheeses, including the famous Pecorino. This stop is a highlight for wine connoisseurs and those interested in local culinary craftsmanship.

After the winery, the tour visits Montepulciano’s historic center. This hilltop town features medieval architecture, with highlights such as the Torre di Pulcinella, a clock tower topped with the figure of Pulcinella from commedia dell’arte. The central square houses the 14th-century Palazzo Comunale and a Duomo with a remarkable triptych on the altar.
This area is perfect for leisurely exploration, with opportunities to browse local shops, admire panoramic views, and enjoy the vibrant atmosphere of a town with Etruscan origins. The visit is brief but well-paced, allowing for photo opportunities and a glimpse into Tuscany’s medieval heritage.

The third stop is the picturesque town of Pienza, famous for its Renaissance urban planning and local culinary products. Built on a hilltop in the Val d’Orcia, Pienza was transformed by Pope Pius II into an ideal Renaissance city, which still influences its charming layout today. Visitors have about 30 minutes to explore the narrow streets, the central piazza, and the historic buildings.
Along With its architectural beauty, Pienza offers a chance to sample local cheeses, both fresh and seasoned, made with genuine, natural ingredients. The town’s culinary fame makes it a favorite stop for those wanting to enjoy authentic Tuscan flavors amid beautiful scenery.

This private tour includes luxury air-conditioned transportation with WiFi on board. The driver speaks English and Spanish, although some reviews mention that English fluency may be limited. The tour features hotel pickup and drop-off, making logistics straightforward for guests staying in Rome.
Included in the price are the wine tasting and winery tour, but not lunch or additional alcoholic beverages. Entrance tickets to the stops are generally free, but guests should be aware of potential purchase opportunities at the local farm or town shops. The tour is designed for most travelers, with service animals allowed but pets needing a carrier.
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The guided winery tour is led by an expert who explains the history of wine and tasting techniques, adding depth to the experience. Alfredo, the winemaker, is known for sharing stories about local wine traditions. In Montepulciano, the guide provides insights into medieval history and points out notable landmarks like the Torre di Pulcinella.
While driver explanations may vary, the overall experience favors knowledgeable guides who enhance the cultural understanding of each location. Some reviews note that English fluency from the driver can be limited but appreciate the professionalism and courtesy.

This Tuscany day trip from Rome appeals especially to those seeking a combination of scenic views, cultural exploration, and wine tasting. The visits to Montepulciano and Pienza showcase Tuscany’s historic towns, while the winery experience offers a taste of local craftsmanship.
Although the price is relatively high, the full-day itinerary and private transportation provide a convenient, curated experience. Travelers should consider their interest in wine, history, and scenic landscapes when choosing this tour.

This tour offers a comprehensive introduction to Tuscany’s highlights, combining wine tasting, medieval architecture, and Renaissance urban planning. The luxury transport and guided experiences make it suitable for adults and families who want to enjoy a full day of cultural and culinary discovery.
While some reviews mention driver language limitations and question value for money, most praise the stunning scenery, knowledgeable guides, and authentic products. It’s an ideal choice for wine lovers and history enthusiasts eager to explore Tuscany’s heart in a single day.
“The winery Canneto and the host Daniela at the winery were the best part.”
Is transportation included in the tour price?
Yes, private, air-conditioned transportation with WiFi is included, along with hotel pickup and drop-off.
How long is the tour?
The entire experience lasts approximately 10 hours, starting early in the morning and returning in the evening.
Are there any dietary restrictions or allergies accommodated?
The tour features wine tastings and local products, but specific dietary accommodations are not mentioned. It’s best to clarify with the provider if needed.
What should I bring for the tour?
Comfortable shoes are recommended for walking in towns, and a camera for photos. Bring cash or cards for any purchases at local shops.
Is this tour suitable for children or pets?
Most travelers can participate, and service animals are allowed. Pets must have a carrier.
Are lunch and additional drinks included?
No, lunch and extra alcoholic beverages are not included; the tour focuses on wine tasting and sightseeing.
Can the driver communicate fluently in English?
The driver speaks English and Spanish, but some reviews note that English fluency may be limited. The guided winery tour is conducted mainly in English.
How is the pacing of the tour?
The itinerary is well-structured, with about 30 minutes at Montepulciano and Pienza, and a 3-hour winery visit, making for a full but manageable day.
Is there a possibility to customize the experience?
This is a private tour, so customization might be possible upon request, though specific options are not detailed in the provided data.
How do I book this tour?
Booking can be done through Fast Travel Services, the experience provider, with confirmation received at the time of booking.