Pienza Tours and Tickets

Q: How much does it cost to visit Pienza in 2026?

Visiting Pienza is free; however, many travelers choose to explore on a tour. Pienza day trips generally start from Florence, Rome, or Siena, and visit Montalcino and/or Montepulciano. Tours can cost from US$65 for a no-frills group tour up to US$950 for a private tour with food and wine.

Q: What is the best way to get to Pienza?

Several buses a day cover the 9 miles (14 kilometers) between Pienza and Montepulciano, but reaching the town from Siena, Florence, or Rome on public transportation is extremely time-consuming. Your best bet is to drive yourself or join a tour: With a tour, you don’t have to worry about parking.

Q: What are the must-see attractions in Pienza?

Pienza’s main attractions, beyond its spectacular city walls, are on its main square: Piazza Pio II. Here you can see an imposing Renaissance cathedral, several glorious palazzos, and the conservatory of San Carlo, now home to an archaeological museum. The Pieve di Corsignano, a Romanesque church, lies just outside the city.

Q: What is the best time of year to visit Pienza?

Like the rest of Tuscany, Pienza is at its busiest over the summer, with high-season prices beginning as early as May and running all the way through September. Planning your trip for April (outside the Easter vacation) or October can mean warmer temperatures but fewer crowds.

Q: Is Pienza accessible?

Yes, with planning, Pienza can be accessible to travelers who use wheelchairs: Its streets are less steep than many Tuscan hill towns. There are wheelchair-accessible hotels, while Piazza Pio II is flat and level. However, the city walls, the cathedral crypt, and some stores and eateries will be off limits.

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Small-Group Montepulciano and Pienza Day Trip from Siena

Discover Tuscany's stunning landscape, culinary delights, and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Avoid the hassle of driving yourself and be led by a local guide. Admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with a visit to a winery.

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Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

4.9

(325)

from $225

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan with an English-speaking driver and complimentary water. Small group experience, maximum 8 participants. Why choose us? • Guaranteed departures • Secure booking • 24-hour cancellation policy • Best rates guaranteed For operational reasons, the itinerary order may vary between Montepulciano and Montalcino.

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Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

4.7

(7)

from $271

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Embark on a delightful day trip through Tuscany's iconic Val d'Orcia, a UNESCO World Heritage Site. Visit Montalcino, home of Brunello wine, Pienza, famed for Pecorino cheese, and Montepulciano, celebrated for Nobile wine. Enjoy breathtaking views, rich culture, and mouthwatering food. Travel in comfort aboard a premium minivan with an English-speaking driver. Indulge in wine tastings, a superior lunch with a view (seasonal), and guided vineyard and cellar tours.

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Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

10 hours 30 minutesFree Cancellation

4.7

(405)

from $271

Price varies by group size

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Pienza and Montalcino are top foodie destinations, but getting there by train and bus can eat hours out of your day. Experience the area's top cheese and wine with ease on this private tour from Siena. Admire the Val d’Orcia scenery, learn about cheese making during an organic dairy farm tour, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine at a Montalcino winery.

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Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

8 hoursFree Cancellation

5.0

(41)

from $828

Per group

Born from a "dream of love and an idea of beauty", Pienza, the ideal city of the Italian Renaissance, is still today an intact testimony of an illustrious architectural project, commissioned by Pope Pius II Piccolomini and made concrete by the great Florentine architect Bernardo Rossellino. Built in a very limited period of time (1459-1462), the city of Pio is the result of a single master plan marked, by the will of the great humanist pope who gave it the name, by design criteria of harmony and aesthetic perfection still today. clearly visible in the small urban center that was Corsignano in the Middle Ages.

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Private Guided Tour of Pienza on Foot

3 hoursFree Cancellation

4.7

(7)

from $248

Per group

Special Offer

Medieval Tour in Monteriggioni and Val d'Orcia from Florence

Experience medieval Tuscany on a group day trip. Visit the fortified town of Monteriggioni with tickets to its Templar Museum and access to its medieval walls. Continue on to the UNESCO heritage area of Val d'Orcia and stop at the medieval village of Montalcino for an optional taste of local wine and nibbles. Finish your tour with a wander through Pienza before the scenic drive back to Florence.

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Medieval Tour in Monteriggioni and Val d'Orcia from Florence

11 hoursFree Cancellation

The Best Way to Discover Siena: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a traditional Ricciarelli almond cookie in a local pastry shop or enjoy the medieval atmosphere of the Piazza del Campo and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups. The "Complete City" Package - Everything you need in one app: Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way. Cultural Context: Read the history and legends of each site as you explore. Insider Tips: Access hand-picked local restaurant and shop recommendations. What you will visit: Pinacoteca Nazionale, Baptistery of St John, Palazzo Piccolomini, Loggia del Papa, Tower of Mangia, Pubblico Palace, Fonte Gaia, Santa Maria della Scala, Facciatone, and the Duomo di Siena.

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Siena Scavenger Hunt & Highlights Self-Guided Walking Tour

2 hoursFree Cancellation

4.2

(12)

from $4

Price varies by group size

Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting

Discover three of Tuscany’s most beautiful towns as you explore Pienza, Montalcino, and Montepulciano in one day on this walking tour. With a private guide, see the splendid 16th-century Renaissance palaces of Montepulciano and walk through the town of Pienza, built by Pope Pius II. In Montalcino, take a guided tour of a winery and taste the renowned Brunello de Montalcino wine. Note: transportation is not included.

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Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting

8 hoursFree Cancellation

5.0

(1)

from $414

Per group

Pecorino Cheese and Brunello Tasting Tour in Tuscany

Discover the rich flavors of Tuscany on this immersive food and wine tour. Begin your day at a family farm in Pienza, renowned for its pecorino cheese, where you'll explore the grounds and enjoy a cheese tasting featuring six varieties, along with homemade accompaniments. Next, savor a delightful three-course lunch paired with Brunello wine in Montalcino, and take a guided tour of the vineyard and aging room. Conclude your adventure in Pienza, heritage UNESCO with a breathtaking view from the town - Explore a family farm in Pienza, the heart of pecorino cheese - Enjoy a tasting of six cheeses with local products and wines - Indulge in a three-course lunch paired with Brunello in Montalcino - Visit the medieval underground city of Montepulciano with a wine tasting

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Pecorino Cheese and Brunello Tasting Tour in Tuscany

9 hoursFree Cancellation

5.0

(8)

from $390

Montepulciano and Pienza Tuscany Wine&Cheese Fullday from Florence

Experience this great FullDay Tour from Florence exploring the Southern Tuscany towns and countryside and see: • Montepulciano • Pienza Included: - Wine Tasting - Pecorino Cheese Tasting Local licensed tour guide in Pienza and Montepulciano (if option selected) Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

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Montepulciano and Pienza Tuscany Wine&Cheese Fullday from Florence

9 hoursFree Cancellation

4.5

from $768

Price varies by group size

Tuscany Tour: Montepulciano, Pienza & Montalcino

Embark on a captivating journey through the Tuscan Countryside, immersing yourself in the timeless beauty of this renowned region, celebrated for picturesque landscapes, historic towns, and exquisite wines. Our adventure begins in Montepulciano, a charming hilltop town renowned for medieval architecture and delectable wines. Explore cobblestone streets, visit historic cellars, and savor the rich flavors that make Montepulciano a haven for wine enthusiasts. Next, venture to Pienza, a UNESCO World Heritage site and birthplace of Pope Pius II. Marvel at well-preserved Renaissance architecture, stroll quaint streets, and indulge in local pecorino cheese—a culinary delight for which Pienza is renowned. Continuing the journey, arrive in Montalcino, a fortress town surrounded by vineyards producing the illustrious Brunello di Montalcino wine. Delight your senses with a wine tasting experience, sampling bold and complex flavors that have made this wine world-famous.

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Tuscany Tour: Montepulciano, Pienza & Montalcino

12 hoursFree Cancellation

5.0

(1)

from $585

Price varies by group size

Montepulciano Wine and Pienza Flavours Private Day Tour from Rome

10 hoursFree Cancellation

4.8

(33)

from $426

Price varies by group size

Explore Pienza From Ideal Renaissance City to Tuscan Views

This tour of Pienza stands out by combining clear Renaissance urban design with authentic local culture and scenic landscapes in a compact and accessible format. The route covers key spaces, beginning at Porta al Prato, continuing along Corso Rossellino, and arriving at Piazza Pio II, where architecture, history, and civic identity come together. It then reveals panoramic views from Via dell'Amore, explores quieter backstreets such as Via del Bacio, and incorporates a culinary stop that highlights regional traditions. Throughout the experience, the tour connects built form with natural surroundings, balances major landmarks with intimate spaces, and allows a deeper understanding of how planning, culture, and landscape interact within a unified setting.

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Explore Pienza From Ideal Renaissance City to Tuscan Views

2 hours

from $236

Price varies by group size

Make the most of your time and avoid the delays of public transportation on this private Montepulciano and Pienza day trip from Florence. Set off directly from your hotel and enjoy free time to sightsee and shop in both Tuscan towns, plus exclusive wine and cheese tastings with local producers. Upgrade to include guided walking tours or explore at your own pace with the recommendations of your English-speaking driver.

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Montepulciano and Pienza Tuscany Wine&Cheese Fullday from Florence

9 hoursFree Cancellation

4.0

from $946

Price varies by group size

Tuscany Tour Montalcino Montepulciano Pienza

A tour between Montalcino and Montepulciano offers an unforgettable journey through breathtaking landscapes, fascinating historic cities and the discovery of two of Tuscany's most celebrated wines. While Montalcino enchants with its rich and complex Brunello, Montepulciano fascinates with its elegant and structured Nobile. Both cities offer a unique experience that combines history, culture and food and wine delights, making a visit to this region an unmissable experience for lovers of wine and Tuscan beauty.

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Tuscany Tour Montalcino Montepulciano Pienza

10 hoursFree Cancellation

5.0

(1)

from $1,052

Per group

Private Tuscany Wine Tour from Rome Montepulciano and Pienza

Leave the bustle of Rome behind and enjoy an elegant private journey into the heart of Tuscany. Travel through the scenic Crete Senesi and the rolling hills of Montepulciano and Pienza, where vineyards, historic villages, and breathtaking countryside create an unforgettable setting. Visit a prestigious local winery and enjoy a guided tasting of Vino Nobile di Montepulciano, regional wines, Vin Santo, artisanal Pecorino cheeses, and extra-virgin olive oil, all fresh and locally produced. Stroll through charming Pienza and immerse yourself in authentic Tuscan beauty, flavors, and relaxed elegance—perfect for couples, families, and wine lovers seeking a refined day trip from Rome.

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Private Tuscany Wine Tour from Rome Montepulciano and Pienza

10 hoursFree Cancellation

4.2

(6)

from $528

Price varies by group size

Discover the Hidden Gems of Val d'Orcia by Vespa!

Explore Quaint Villages and Timeless Landscapes Our journey will take you off the beaten path, winding through both lesser-known hamlets and iconic landmarks alike. Immerse yourself in the rich history and culture of each village we visit, from hidden gems tucked away in the countryside to well-known destinations steeped in tradition. Capture Every Moment, Embrace Every View As we traverse the rolling hills and winding roads, there will be ample opportunities to pause and soak in the panoramic views. Experience the Joy of Open-Air Travel Feel the sun on your face as you cruise through the Val d'Orcia on your Vespa. This isn't just a tour – it's an immersive journey into the heart of Tuscany's natural beauty. Let the open road be your guide as you embrace the freedom of outdoor exploration. Don't Miss Out on This Unforgettable Experience Join us for a Vespa adventure like no other and discover the magic of Val d'Orcia in a whole new way.

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Discover the Hidden Gems of Val d'Orcia by Vespa!

4 hours

5.0

from $296

Price varies by group size

Private tour Wine and cheese a perfect combinations val 'Orcia

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a full day dedicated to wine and cheese, exploring the heart of Tuscany. Drive through the Val d'Orcia, a UNESCO World Heritage Site, and savor some of the region’s finest red wines, including Vino Nobile di Montepulciano and Brunello di Montalcino. Stroll through the medieval squares of Pienza and sample authentic Tuscan cheeses at a historic estate, featuring one of the most breathtaking terraces overlooking the Orcia Valley.

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Private tour Wine and cheese a perfect combinations val 'Orcia

8 to 9 hoursFree Cancellation

4.6

(7)

from $544

Price varies by group size

Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch

9 hoursFree Cancellation

4.5

(17)

from $819

Price varies by group size

Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

Journey to the origins some of Italy’s most celebrated ‘vino’ on a private, full-day tour designed for wine lovers and connoisseurs. Visit the medieval town of Montalcino at the famed of Brunello di Montalcino wine. Taste this prized elixir at a winery. Learn about the area’s history and winemaking heritage from a private guide and meet local producers. Price is per group, with a maximum of either 3 or 8 passengers, depending on season and vehicle type.

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Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

9 hoursFree Cancellation

4.9

(100)

from $917

Per group

I was Born and raised in this magical region od Tuscany, I have key villagers that I have known for many years and you know in Italy is all about relationships...I go above and beyond to take care of my clients. One thing that makes me unique is that I have lived abroad for several years and my spoken English is excellent, this is very important for you to maximize your tour and investment, I comunicate well and I know how to relate to the culture overseas. One other thing is I can sure teach you history but what my clients love about me is the stories and secret I tell them and one thing is for sure...you will laugh and not be the usual boring tour!!!!!

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Val D'Orcia Dreaming!!

4 hoursFree Cancellation

5.0

(20)

from $232

Gladiator Path Hiking Experience in Val d’Orcia

This hiking tour leads you into the heart of the Val d’Orcia, considered the most picturesque area of Tuscany, famous for its rolling hills, cypress-lined roads, and timeless countryside. A UNESCO World Heritage Site, this landscape represents the iconic Tuscan postcard known worldwide. What truly sets this experience apart is the chance to walk the same paths made famous by Ridley Scott’s movie Gladiator. The unforgettable scenes of Russell Crowe walking through golden grain fields were filmed just outside the village of Pienza, a detail still unknown to many travelers. During an easy and scenic hike, suitable for most fitness levels, you will enjoy authentic Tuscan views far from the crowds, while learning about the land and local traditions. The tour also includes time in Pienza, the ideal Renaissance city created by Pope Pius II, where art, architecture, and local flavors—especially the famous Pecorino di Pienza cheese—complete a unique blend of nature, cinema, and Tuscan culture.

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Gladiator Path Hiking Experience in Val d’Orcia

5 hoursFree Cancellation

5.0

from $201

Price varies by group size

Private Day Trip Guided Tour in Val D'Orcia Region from Florence

9 to 10 hoursFree Cancellation

5.0

(6)

from $443

Price varies by group size

Private Taste of Tuscany Tour

9 hoursFree Cancellation

5.0

(3)

from $390

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What are people saying about Pienza

Small-Group Montepulciano and Pienza Day Trip from Siena

bruce_e, Sep 2026

We had a wonderful...

We had a wonderful exposure to the part of Toscany that you see on postcards and in the movies. Pienza and Montepulciano were a nice change of pace from Sienna, Volterra, etc. Our was extremely informative and a pleasure to spend the day with.

Private Guided Tour of Pienza on Foot

Mark_C, May 2026

Great

Guide extremely knowledgeable. Really enjoyed conversation and meeting locals. Duration of tour was good. Provided great perspective of Pienza.

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Madeleine_R, Apr 2026

So much fun! The farm was...

So much fun! The farm was a definite highlight -- gorgeous views and incredible snacks to kickstart the day! We loved getting to walk around Pienza, and the wine was incredible (though definitely pricey if you wanted to purchase bottles to ship home). All in all a perfect way to explore Tuscany. We also loved our guide Frederico! The perfect balance of informational and letting us relax without pressure.

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Catherine_M, Sep 2026

Fun day in Tuscany

Lovely day in Tuscany tasting wine and the lunch was at an amazing place with fabulous views. Also had some time to wander around two very quaint towns.

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

tashhackett, Sep 2026

Great way to see a small part of Tuscany

We didn’t have a car so this was a great option for us - ticks off a few regions, two wine tastings, lunch and our guide Leonardo was informative and friendly! It’s nice to have free time in each area and was such a treat to visit the last winery … gorgeous views & wine, and such history with a 26-generation family run business! A long day but so nice to not have to think about how to get to the next place and just enjoy the ride.

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Bram_D, Aug 2026

We had a wonderful...

We had a wonderful experience! Our driver was incredibly knowledgeable and friendly. He was training a new driver who was also kind. We were the only two guests on the tour because it’s the slow season, so we were quite lucky! Highly recommend. The food and wine were plentiful and delicious!

Small-Group Montepulciano and Pienza Day Trip from Siena

Catherine_D, Jun 2026

Tutto benissimo

10/10 would recommend. Keko was a knowledgeable and charismatic tour guide. While we drove through the Tuscan countryside, he provided engaging commentary about the history, the landscape, and the local food traditions of the region. If you want to see the Tuscan country, this is the way to do it. I particularly enjoyed the lunch at the farm and tasting the local recipes with ingredients made right there. The time in Pienza and Montepulciano flew by. I would definitely take this tour again.

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Jillian_D, Jun 2026

A day of amazing food and wine

Wonderful full day experience in Val d’Orcia! The wine tasting with food pairing in Montepulciano is very well done, the lunch in Pienza is delicious and in a beautiful setting, and the winery visit in Montalcino is great! Our guide/driver Lucca was amazing and very friendly! Highly recommend this tour for anyone looking to venture out of the city to taste exceptional wine and food!

Pienza

5.0

(1,082)

Tuscany

Know before you go

Aerial view of the medieval village of Pienza near Siena, Italy.

Wear comfortable walking shoes; the town is best explored on foot.
Some tours of Pienza may include entrance fees, transportation, guides, food, and drink; check with your tour company for details.xa0
Pienza, while small, makes a great home base for exploring the area, and there are a number of hotels in town.

Pienza Tours and Tickets

63 results

What are people saying about Pienza

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