1 day
Italy Day Tour: Explore Val d'Orcia, Tuscany | Montepulciano + Historic Center of Pienza + Wine and Cheese Tastings (Departing from Rome · English-Speaking Group)
From 30/10/2026
Group Tours
Venture into the heart of Tuscany, visit Montepulciano’s famous Talosa wine cellar, savor authentic Tuscan flavors, and admire the breathtaking, picture-perfect panoramas of Val d’Orcia.
Rome - Montepulciano - Pienza - Rome
Upcoming departure dates: 2026-10-30, 2026-11-01, 2026-11-07, 2026-11-08, 2026-11-14, 2026-11-15, 2026-11-21, 2026-11-22, 2026-11-28, 2026-11-29
Day 1
Rome - Montepulciano - Pienza - Rome
Download full itinerary PDFTour departure point
D1 Rome (Roma) Tour departure time: 07:30 Meeting point: Piazza del Popolo, Rome (in front of the obelisk in the center of the square)
Itinerary details
Set out from Rome on a day trip deep into the heart of Tuscany and experience the enduring charm of this timeless land. Golden sunlight falls across rolling hills, while endless vineyards, country roads lined with cypress trees, and charming hilltop towns combine to create the unforgettable pastoral scenery of the Val d’Orcia. First, visit the Renaissance gem of Montepulciano. This historic hill town is renowned for producing Vino Nobile di Montepulciano, a world-famous, high-quality red wine. Enjoy free time to stroll through the elegant, charming streets of the old town and soak up its rich history. Next, visit Cantina Talosa. Built in the 16th century, this magnificent historic cellar was carved entirely into tuff rock and lies deep beneath the old town. Walk among ancient brick vaults and aged oak barrels as you learn about Tuscany’s long-standing winemaking traditions and culture. In this atmospheric historic underground cellar, sample 3 to 4 carefully selected wines, including Vino Nobile di Montepulciano, and discover the authentic flavors and local traditions of Tuscany. In the afternoon, continue to Pienza, known as the “ideal Renaissance city.” This elegant old town sits amid the spectacular Val d’Orcia and is a UNESCO World Heritage Site. Stroll along its harmonious, thoughtfully planned streets, take in sweeping views of the Tuscan hills, and enjoy free time to immerse yourself in the unique charm of this architectural masterpiece. Beyond its architecture and history, Pienza is also known for its long cheese-making tradition. Sample Pecorino di Pienza, a local specialty, and savor its delicate, rich, and layered flavors. After this memorable journey combining art, history, wine, food, and breathtaking scenery, travel back to Rome by coach. On the return journey, reflect on your wonderful memories of classic Tuscany and bring this unforgettable day trip to a perfect close. Approximate tour duration: 12 hours Important information and helpful tips Comfortable walking shoes are strongly recommended (the old towns have mostly cobblestone streets, and some sections are steep and uneven). Please let us know in advance if you have any food allergies or special dietary requirements. This tour involves walking and climbing stairs to enter an underground cellar. It is not suitable for people with limited mobility, wheelchair users, or travelers with severe mobility impairments. Please arrive at the meeting point at least 20 minutes before departure.
Important notes
Note: All times shown on this webpage are for reference only. Actual arrival times may be delayed due to circumstances beyond our control, such as weather, traffic congestion, traffic accidents, festivals or sporting events, civil unrest, or strikes. We appreciate your understanding. If you have onward travel plans involving other transportation to another city, we strongly recommend allowing at least 3 hours of extra time to avoid inconvenience caused by delays. Our company accepts no responsibility for losses arising from travel arrangements you make yourself without allowing sufficient extra time. Thank you for your understanding.
Meals
Breakfast: at your own expense Lunch: at your own expense Dinner: at your own expense
Accommodation
None
Pricing Information
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Included:
Round-trip transportation from Rome by luxury air-conditioned coach
Professional tour leader service
Free time to explore Montepulciano Old Town
Free time to explore Pienza Old Town
Taste 3–4 selected wines, including Vino Nobile di Montepulciano, at a historic winery in Montepulciano
Pecorino di Pienza cheese tasting
Not included:
Items not listed above under “What’s excluded”
Booking information
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Changes and cancellation policy
Free cancellation up to 72 hours before departure.
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Choose your date, departure point and room type, then review the total before booking.
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