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 ¥20,435 per night from Nov 8 to Nov 9
¥20,435
¥23,541 total
Nov 8 - Nov 9
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 ...
9.4/10 Exceptional! (161 reviews)
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"

Reviewed on Oct 8, 2026

Hotel San Gregorio
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11 Pienza SI
The price is ¥21,874 per night from Nov 8 to Nov 9
¥21,874
¥25,124 total
Nov 8 - Nov 9
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 ...
Hotel Corsignano
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
The price is ¥21,377 per night from Nov 5 to Nov 6
¥21,377
¥24,222 total
Nov 5 - Nov 6
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! (81 reviews)
"We stayed at the olive Farmhouse across the street from the main property. Rooms were cozy and clean with some interesting toiletries to use (made from olive oil). The property also has a range of activities (extra) to choose from. Just a note that eventhough the farmhouse is close to the main property, ..."

Reviewed on Oct 6, 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 ...
9.4/10 Exceptional! (161 reviews)
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"

Reviewed on Oct 8, 2026

Hotel San Gregorio
 House with private pool  with beautiful view Val d 'Orcia

House with private pool with beautiful view Val d 'Orcia

Monticchiello Tuscany
Stay at this vacation home in Pienza. Enjoy free WiFi, private pools, and a garden. Popular attractions Art Studio di Adelina Quadri and Via del Casello are ...
9.8/10 Exceptional! (50 reviews)
"We had an incredible stay at Agriturismo Collosodo. The views from the house are stunning, the pool is fantastic, and the grounds are beautifully maintained and filled with fruit trees. We were lucky to visit at the end of August when the figs were ripe and ready to be picked straight from the trees. ..."

Reviewed on Aug 30, 2026

House with private pool with beautiful view Val d 'Orcia
Samsara Apartment elegant apartment in the historical center.

Samsara Apartment elegant apartment in the historical center.

Pienza Provincia di Siena
Book a stay at this family-friendly apartment in Pienza. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Corso il Rossellino ...
10/10 Exceptional! (4 reviews)
"Great host. Nice apartment."

Reviewed on Sep 14, 2026

Samsara Apartment elegant apartment in the historical center.
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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