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Pienza and Montepulciano Tour
Explore the Renaissance charm of Pienza, indulge in organic farm-to-table dining and savor the architectural beauty and renowned wines of Montepulciano

Pienza and Montepulciano Tour

Meet your guide at 9:30 a.m. in front of the Church of San Domenico in Siena, an easy meeting point even for those arriving by car, with parking available nearby. From here, travel south along one of Tuscany’s most scenic roads, crossing the striking clay landscapes of the Crete Senesi. Enjoy short photo stops along the way before visiting a charming, non-touristy medieval hamlet.

Continue through this breathtaking countryside to the UNESCO-listed Val d’Orcia, home to some of Tuscany’s most iconic postcard views. Your next stop is Pienza, the harmonious Renaissance town commissioned by Pope Pius II and designed by leading architects of the time as an ideal city. Spend free time exploring the Renaissance Cathedral, the Romanesque Church of Corsignano, and the panoramic walkways overlooking the surrounding valleys. Wander through the picturesque streets and browse local artisan shops.

Lunch is hosted at a local farm, featuring fresh, seasonal products mostly produced on site. Learn about pecorino cheese making, meet the farm animals, and discover rural Tuscan life. Weather permitting, enjoy lunch on a panoramic terrace.

In the afternoon, visit Montepulciano, one of Tuscany’s most impressive hill towns. Explore Piazza Grande, admire Siena and Florence’s architectural influences, visit an underground winery, and taste the renowned Vino Nobile. After a guided walk, enjoy free time or an optional cellar tour.

Photo Gallery

Tour Information

  • Tour Code : SMITSICU12
  • Type : Small Group Tour
  • Category : Car/Van Tours
  • Duration : 9 Hours
  • Departure City : Siena, Italy
  • Departure : Guaranteed Departure
  • Grade/Difficulity : Easy To Moderate
  • Transport Mode : Car/Minivan
  • Children Allowed : Yes
  • Min Group Size : 2
  • Max Group Size : 8
  • Arrangement : Driver-Guide
  • Entrance Fee : No inside visits
  • Hotel Pickup : No
  • Language Offered : English
  • Hotel Dropoff : No
  • Meeting Time: 09:30 AM
  • Starting/Meeting Point : Piazza San Domenico, Siena
    Meet the tour guide under the large tree (there is seating) that is in front of the church steps.
    Please, arrive 15 minutes prior to the start of the tour.
Availability
From March 2026 To December 2026
English - Every Monday,Thursday,Saturday
Highlights
  •  Discover the architectural beauty and Renaissance charm of Pienza, a UNESCO World Heritage site, with its stunning cathedral, central square, and breathtaking views of the Val d'Orcia.
  •  Indulge in a delicious organic lunch at a family-run farm nestled in the heart of the Val d'Orcia.
  •  Wander the medieval streets of Montepulciano, known for its Renaissance architecture and famous Vino Nobile wine.
  •  Explore the charming medieval towns of Pienza and Montepulciano at your own pace.
  •  Travel in comfort as you take in the UNESCO-protected landscapes of Val d'Orcia.
Tour Includes
  •  Self-guided visit of Pienza and Montepulciano
  •  Lunch on organic farm with spectacular views
  •  Tour historic wine cellars
Notes
  •  The route may change according to traffic conditions and availability of wineries.
  •  The wineries included in the tour may be substituted with others of a similar level, according to availability.

Pricing

FromToPer Pax
Mar 1, 2026Apr 30, 2026Monday,Thursday,SaturdayOn Request
May 1, 2026Jun 30, 2026Monday,Tuesday,Thursday,Friday,Saturday,SundayOn Request
Jul 1, 2026Aug 31, 2026Monday,Thursday,SaturdayOn Request
Sep 1, 2026Oct 31, 2026Monday,Tuesday,Thursday,Friday,Saturday,SundayOn Request
Nov 1, 2026Dec 31, 2026Monday,Thursday,SaturdayOn Request