Pienza

Travel Guide

A historic square with a prominent tower and statues.
A historic street with pedestrians, a bar, and a building with a fresco.
A narrow street with old buildings, wooden shutters, and potted plants.
A stack of large wheels of cheese with a price tag, surrounded by clusters of red and black grapes.
A park with benches, trees, and a street in the background.

Marvel at architectural wonders, browse artisan’s shops and people-watch at pavement cafés in this Renaissance town set amid Tuscany’s glorious countryside.

Pienza is a storybook hill town and a popular place to visit in Tuscany’s Siena province. Originally called Corsignano, it is Italy’s first planned town, born out of the vision of Enea Silvius Piccolomini. After becoming Pope Pius II in 1458, Piccolomini set about creating a Renaissance town with majestic churches, palaces and squares. Today, Pienza is a UNESCO World Heritage Site and its walled old town bears testament to the late pope’s dream.

Start your visit at Piazza Pio II, the historic quarter’s central square. Gaze in awe at the Cathedral of PienzaOpens in a new window, home to work by artists from the Sienese School. Explore the regal rooms of Palazzo Piccolomini, built as a summer retreat for the pope and his family. The palace’s manicured garden affords uninterrupted views over the Val d’Orcia valley.

On the square’s east side is the Palazzo Borgia. It houses the Diocesan Museum, which has exhibitions of art and jewelry from the 13th to 19th centuries.

Brick-paved streets radiate from Piazza Pio II and lead to pretty squares, characterized by houses with shuttered windows and flower-filled balconies. Peek inside handicraft stores and watch the world go by from a café terrace. Look for the medieval Church of San Francesco, which predates the town’s urban makeover.

Stroll around the exterior of the town walls and pause at imposing gateways, including Porta al Prato. Go to the Romanesque hillside church, Pieve di Corsignano. Stay a while and admire the olive groves and vineyards of Val d’Orcia.

A fun time to visit Pienza is in early September for the Fiera del Cacio, a celebration of the locally produced pecorino cheese. Don’t miss the Palio del Cacio Fuso, when people compete in a closest-to-the-target cheese-rolling contest. Sample pecorino cheese at the festival’s market stalls or year-round at the town’s osterie (taverns).

Pienza is about a 1-hour drive southwest from SienaOpens in a new window. Street parking is available for a fee outside the walled district and there’re designated bicycle parking areas, too. An idyllic daytrip and weekend destination, Pienza is also a great base for visiting Val d’Orcia’s other hill towns such as MontalcinoOpens in a new window and MonticchielloOpens in a new window.

Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
The price is ¥30,944 per night from Oct 10 to Oct 11
¥30,944
¥35,107 total
Oct 10 - Oct 11
includes taxes & fees
Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions Enoteca Di Ghino and Artemisia ...
Hotel San Gregorio
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11 Pienza SI
The price is ¥31,251 per night from Oct 10 to Oct 11
¥31,251
¥35,445 total
Oct 10 - Oct 11
includes taxes & fees
Book a stay at this family-friendly hotel in Pienza. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (381 reviews)
"My husband and I had an absolutely wonderful experience at Hotel Corsignano. From beginning to end, the staff went above and beyond to make us feel welcome and cared for. When we arrived a little later than expected, they were genuinely concerned about us and even made sure to save a parking spot ..."

Reviewed on Sep 12, 2026

Hotel Corsignano
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
The price is ¥38,617 per night from Oct 9 to Oct 10
¥38,617
¥43,191 total
Oct 9 - Oct 10
includes taxes & fees
Book a stay at this family-friendly hotel in Pienza. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (73 reviews)
"During our 2.5 week trip to Tuscany, we stayed 4 nights. True hospitality. Vera served our breakfast daily and wanted to help in any way possible."

Reviewed on Sep 4, 2026

Agriturismo Il Macchione
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions Enoteca Di Ghino and Artemisia ...
Hotel San Gregorio
Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri

Corso il Rossellino 91 Pienza SI
Stay at this apartment in Pienza. Enjoy free WiFi. Popular attractions Palazzo Vescovile and Museo Diocesano are located nearby.
10/10 Exceptional! (3 reviews)
"Location was in the middle of the ZTL in Pienza which means you get to walk out of your room into the middle of the touristy part of the city with no cars to really worry about most of the time. Parking was about a 10 min walk away so it wasn't too bag to walk with bags. Cute suite we had with a ..."

Reviewed on Jun 29, 2026

Casa Gioia - Casa Olivieri
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

Pienza Tuscany
Book a stay at this family-friendly villa in Pienza. Enjoy free WiFi, private pools, and a garden. Popular attractions Piazza delle Sorgenti and Tenuta Sanone ...
10/10 Exceptional! (6 reviews)
"Een prachtig huis, alles prima in orde. Groot en proper zwembad. Een fijne ontvangst door de host.En een fenomenaal zicht op de mooie omgeving!"

Reviewed on Jul 12, 2026

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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