Montepulciano & Pienza: the soul of Southern Tuscany

Cod: N/A
Tour Date 06/05/2026

Tour Description

This day tour from Florence explores the heart of southern Tuscany, where rolling hills, historic wine towns, and Renaissance villages define the landscape. From the underground cellars of Montepulciano to the harmonious streets of Pienza and the refined atmosphere of Montalcino, the itinerary blends wine culture, scenic drives, and relaxed free time, offering participants an authentic taste of the Val d’Orcia.

Tour Services

  • Pick-up and drop-off in Florence (Piazza dell’Unità Italiana, 50123 Firenze FI) – standard meeting point.
  • Transportation by comfortable, air-conditioned Mercedes-Benz minivan with professional English-speaking driver.
  • Guided wine tasting experience in Montepulciano.
  • Free time in Montepulciano, Pienza, and Montalcino.
  • Scenic drive through the Val d’Orcia, including the area of San Quirico d’Orcia.

 

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Morning – Florence to Montepulciano
Accordion

The day begins with a departure from Florence, heading south through the Tuscan countryside toward the hill town of Montepulciano. Vineyards, olive groves, and gently rolling hills accompany the journey, setting the tone for a day dedicated to wine and landscape (Approximately 1 hour and 45 minutes drive).

Upon arrival, participants step into the heart of local winemaking traditions with a guided wine tasting at one of Montepulciano’s most renowned historic wineries, located beneath the medieval streets. In the atmospheric cellar, selected wines are tasted while learning about the production of Vino Nobile di Montepulciano (Approximately 1 hour).

Late Morning – Free Time in Montepulciano
Accordion

Following the tasting, free time allows participants to explore Montepulciano independently. Renaissance streets invite leisurely walks, panoramic viewpoints open over the Val d’Orcia, and local artisan shops offer opportunities for browsing and photography (Approximately 30 minutes free time).

Midday – Pienza
Accordion

Leaving Montepulciano, the journey continues along scenic roads framed by vineyards and cypress trees toward Pienza  (Approximately 30 minutes drive).

Once in Pienza, participants enjoy free time for lunch in this perfectly preserved Renaissance town, celebrated for its pecorino cheese. Time is available to dine at a local trattoria, sample regional specialties, or stroll through picturesque streets overlooking the Val d’Orcia (Approximately 1 hour and 30 minutes – lunch not included).

Afternoon – Val d’Orcia and Montalcino
Accordion

In the afternoon, the route unfolds through one of Tuscany’s most iconic landscapes. A panoramic drive through the Val d’Orcia, passing the area of San Quirico d’Orcia, reveals postcard-worthy scenery of rolling hills and historic villages (Approximately 45 minutes drive).

The tour then reaches Montalcino, where free time is available to explore the historic center. Participants may visit local enotecas to taste or purchase Brunello di Montalcino, or simply enjoy the refined atmosphere of this renowned wine town (Approximately 1 hour free time).

Return to Florence
Accordion

In the late afternoon, the journey back to Florence begins. The return drive offers time to relax and reflect on a day shaped by world-class wines, breathtaking landscapes, and the timeless charm of southern Tuscany (Approximately 2 hours and 30 minutes drive).

Terms and Cancellation policies
Accordion

Art. 1 terms and regulations:

  • Group capacity:  min 10 pax – max 20 people per group 
  • If the group tour does not reach the minimum capacity of participants by 72 hrs prior the start of the tour, it will be cancelled.
  • In case of the cancellation by the great italy tour, the great italy tour will return the amount paid by the customer via nexi payment platform.

 

Art. 2 – cancellation policy on behalf of the client:

  • Once customers pay the amount of a day tour, in the case of the eventual withdrawal on behalf of the client for any reason before departure, the client will be charged the following percentage of the participating shares, calculated taking into consideration how many days before departure he/she has requested the cancellation. From the day following the booking until:

 
– 6 days pre-departure 0% (free cxl till 5 days prior the tour)
– 5-0 days pre-departure 100%.

  • By confirming the reservation and making the payment, you accept the regulation and the itinerary as previously described.

 

Art. 3 – tour variations

  • The service providers (hotels, agritourisms, restaurants, chefs, etc.) At times mentioned in our tour itineraries are subject to change. In this unlikely event they will only be substituted by others of equal or better quality in order to avoid affecting the content of our services.
  • The itineraries are subject to changes. Suggested activities may have to be substituted as a result of natural disasters, sudden atmospheric changes, temporary closures, striking or any other problems for which the tour organizers may not be held accountable. Any alterations made will be done so in order to improve the service on offer and will always be of equal commercial value.