PIENZA, ITALY: TRAVEL GUIDE TO THE PRETTIEST TOWN IN TUSCANY
For years I’ve heard people gush over Pienza and claim the hilltop town to be the most beautiful destination in Tuscany. It was the place I most wanted to visit on this trip, and I can confirm it lives up to its reputation. Perched high above the Val d’Orcia, the perfectly preserved Renaissance stone village was commissioned in the 15th century by Pope Pius II as an “ideal city.” Pienza is small, but mighty; filled with charming stone alleys, a picturesque piazza, little trattorias, cheese shops and sweeping views of the Tuscan countryside. Below is my complete travel guide to Pienza including the best places to visit, viewpoints, restaurants, hotels, Pienza photo locations, travel tips and more.
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The gorgeous cypress lined drive to Palazzo Massaini.
PIENZA TRAVEL TIPS
- CURRENCY – The official currency of Italy is the Euro. While most places take credit card, it’s always handy to have cash for smaller purchases, etc.
- STAYING CONNECTED – Almost all hotels and restaurants have free wi-fi available to guests, but for connection 24/7 download an e-SIM for your cell phone.
- TIPPING – Tipping is not customary in Italy, servers are paid living wages.
Gelato stop in Pienza. OUTFIT DETAILS: Aerie dress linked here, Sezane bag linked here and Target sandals linked here.
WHEN TO VISIT PIENZA
- APRIL, MAY, SEPTEMBER, OCTOBER – Shoulder season is the best time of the year in Tuscany. Crowds can’t be avoided, but it won’t be as busy as summer, temperatures are more manageable and hotel prices are a bit more reasonable.
- JUNE-AUGUST – Summer is the busiest time of the year throughout Italy. Make all reservations well in advance.
- NOVEMBER-MARCH – Hotel prices are more affordable in low season when crowds thin out, but you risk cooler weather.
HOW MANY DAYS IN PIENZA
It’s easy enough to explore all of Pienza in a half-day visit. The town is small, and it doesn’t take long to walk end to end, visit the historical sights and soak in the views. For a longer stay, Pienza is a fabulous base for day trips around Tuscany.
The town is filled with charming pedestrian lanes.
PLACES TO VISIT IN PIENZA
PALAZZO PICCOLOMINI
This beautiful palazzo is one of many Renaissance relics in Pienza that dates back to the 15th century when the town was built. Architectural details include a three-tiered loggia, stone facade, pillars, mullioned windows and a symmetrical central courtyard.
PIENZA CATHEDRAL
This gorgeous cathedral sits on the Piazza Pio II in the heart of Pienza. The beautiful facade is made of local travertine that glows when the sun is up. It’s a prime example of geometrical symmetry that characterizes the architecture of the Renaissance.
PIAZZA PIO
Piazza Pio sits in the heart of Pienza. It’s the main gathering place in town, a brick-laid square designed in a trapezoidal shape. The piazza is beautiful, surrounded by the Pienza Cathedral, Palazzo Piccolomini and the Palazzo Comunale. My favorite spot in the square is the Pozzo dei Cani, a lovely historic stone well perfect to sit with a gelato and people watch.
PIENZA STREETS
Spend the morning exploring the cobbled lanes that weave through town. All of Pienza is picturesque, but make a point to visit these three particularly lovely streets: Via del Leone, Via della Volpe and Via Dogali.
VIA DEL CASELLO
This stone pedestrian path lines the town walls and overlooks stunning views of the surrounding patchwork scenery. The views are extensive and unobstructed, so there’s a spot for everyone even if its busy.
Palazzo Massaini is a stunning agriturismo located five-minutes from Pienza.
BEST PIENZA HOTELS
Located just 10 minutes from Pienza in the hills of the Val d’Orcia, Casa Newton is a gorgeous crimson colored villa outfitted with green shutters that dates back to the 19th century. It houses 11 rooms and suites that blend vintage details with modern creature comforts. Rooms are airy with wood beam ceilings, terracotta tiles, woven walls and luxurious amenities.
Another restored farmhouse located a short drive from Pienza. La Saracina offers guests a minimalist but sophisticated stay in one of six rooms converted from the estate’s former stables that look out into the lush gardens. Each room is named after a Tuscan wine including Canaiolo, Malvasia, Prugnolo, Sangioveto, Saragiolo and Trebbiano.
Located just steps away from the walls of Pienza, Hotel San Gregorio sits in a restored 18th century building. The rooms, gardens and pool are perfectly comfortable, but the property doesn’t have the wow factor that so many Tuscan stays offer. Location is fabulous though.
For the ultimate slow-paced stay, L’Olmo sits in a restored 17th century farmhouse located 10 minutes from Pienza. The highlight of the hotel is the infinity pool and surrounding sun beds that overlook a completely iconic Tuscan view. There are only a handful of rooms at L’Olmo, a beautiful mix of rustic Tuscany and modern luxury.
It’s a 15-minute drive to reach Lupaia from Pienza, but worth the journey to stay at this restored 17th century estate. The 12 rooms and suites are gorgeous, and full of rustic character featuring brick archways, stone hearths, vaulted ceilings, wood beams and absolutely incredible balcony views of surrounding Tuscany. This place is a gem and a great base for exploring Montepulciano and Pienza.
It’s hard to miss Palazzo Massaini on the drive into Pienza. The 13th century stone castle sits perched on a hilltop with a cypress lined gravel drive that connects it to the main road. It looks like a Tuscan painting.
The handmade pasta and sauces at Trattoria da Fiorella are delicious – one of the best restaurants in Pienza.
PLACES TO EAT IN PIENZA
- BACCANO IL PANINO TOSCANO – Italian
- BUON GUSTO GELATERIA – Gelato
- FREDO GELATERIA ARTIGIANALE – Gelato
- LA FONTE AGRITURSMO – Italian
- L’OSTERIA BACCUS – Italian
- SETTE DI VINIO – Italian
- TRATTORIA DE FIORELLA – Italian
- TRATTORIA LATTE DI LUNA – Italian
The alleys are lined with cute wine shops and wine bars.
GET AROUND PIENZA
The historical center is a Zona a Traffico Limitato, an area that restricts most vehicles. Be prepared to explore Pienza on foot and get lost in the maze of alleyways and cobbles streets.
Pienza lives up to its reputation as the cutest town in Tuscany.
GET TO PIENZA
- CAR – Several paid parking lots are located just outside the historic walls of Pienza, as well as plenty of paid street parking (look for blue lines!).
- FLIGHT – The Amerigo Vespucci Airport (FLR) in Florence is a 90-minute drive, and the closest airport to Pienza. Alternatively, the Pisa International Airport (PSA) offers more flight options, but it’s a two-hour 20 minute drive from Pienza.
- TRAIN – There are no train stations in Pienza, the closest ones are in Chiusi-Chianciano Terma or Buonconvento.
The pedestrian streets are lined with little shops that sell cheese, olive oil, charcuterie meat and pasta.
Wisteria in full bloom in Pienza in April.
