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.

50 results

Best Seller

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

(386)

from $269

Price varies by group size

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

(6)

from $247

Per group

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

(312)

from $223

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

DEPARTURE GUARANTEED! Enjoy a perfect day trip visiting 3 of the most impressive places in Tuscany. Montalcino, house of "Brunello" wine; Pienza, well known for the "Pecorino" cheese and Montepulciano where the undisputed symbol is the "Nobile di Montepulciano" wine! Please note that from November to April I cannot guarantee the restaurant with view, as stated in the inclusions. The Valdorcia has been recognized as UNESCO world heritage site since 2004, as it was an inspiration for many Renaissance painters. There you will be surrounded by impressive views, art, culture, amazing wine and delicious food! Your semi private tour will be on board of a premium minivan with an English speaking driver, air conditioning and free water. WHY CHOOSE ME? Secure bookings, Guaranted Departures! 48 hours Cancellation policy, best rates guaranteed! Group of maximum 8 people.

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Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

4.8

(4)

from $269

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 $411

Per group

Special Offer

Siena Scavenger Hunt & Highlights Self-Guided Walking Tour

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

4.1

(10)

from

Price varies by group size

Experience medieval Tuscany on a group day trip. Visit the fortified town of Monteriggioni with tickets to its Templar Museum and panoramic views from its walls (if selected). 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

4.8

(65)

from $51

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

(36)

from $823

Per group

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 $294

Price varies by group size

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 $294

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

5.0

(97)

from $912

Per group

Likely to Sell Out

Private Tour: Orcia Valley to Montalcino and Montepulciano with Brunello Wine Tasting

Taste your way through Tuscan wine country on a private, full-day tour from Florence. Travel through the scenic Orcia Valley and visit the birthplaces of several prized Italian wines. Explore the medieval villages, tour historic wine cellars and vineyards, or savor a farm-fresh lunch (own expense): your private driver and guide customizes the itinerary for you. Price is per group, based on a maximum of 7 passengers per vehicle.

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Private Tour: Orcia Valley to Montalcino and Montepulciano with Brunello Wine Tasting

9 hoursFree Cancellation

4.9

(16)

from $1,161

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

(19)

from $231

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 $582

Price varies by group size

Montepulciano and Pienza: Private Wine Tour from Rome

Indulge in the Soul of Tuscany Experience an exclusive day of relaxation and world-class flavors. Journey through the iconic Val d'Orcia (UNESCO site), where rolling green hills and cypress-lined roads create the perfect backdrop for your private escape from Rome. Montepulciano: Home of the "King of Wines" Visit a prestigious local estate for a VIP cellar tour and vineyard walk. You will taste 5 exquisite wines, including the legendary Vino Nobile di Montepulciano DOCG and sweet Vin Santo, paired with authentic extra-virgin olive oil. Pienza: The Renaissance Jewel Famous for its "ideal" architecture and world-renowned Pecorino cheese, Pienza offers breathtaking views over the Tuscan valleys. Discover genuine, farm-to-table products directly from the producers. Why choose us? Avoid the stress of driving and enjoy the wine. With a luxury vehicle, onboard WiFi, and a professional driver at your full disposal, you’ll experience Tuscany like a true connoisseur.

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Montepulciano and Pienza: Private Wine Tour from Rome

10 hoursFree Cancellation

4.5

from $501

Price varies by group size

Likely to Sell Out

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

4.5

(6)

from $541

Price varies by group size

Private Tuscany Wine Tour: 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: Montepulciano and Pienza

10 hoursFree Cancellation

4.2

(6)

from $526

Price varies by group size

Montepulciano Wine and Pienza Flavours Private Day Tour from Rome

Take some time away from the hustle and bustle of the Eternal City, and recharge in the Tuscan countryside with this private tour of Montepulciano and Pienza from Rome. Enjoy convenient pickup from your Rome hotel before you head off to explore both towns, as well as visit a winery and farm for tastings and lunch (at your own expense). Great for travelers who want to see more of Italy outside of the Lazio region.

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Montepulciano Wine and Pienza Flavours Private Day Tour from Rome

10 hoursFree Cancellation

4.8

(33)

from $423

Price varies by group size

Full Day PRIVATE Guided Tour in Val D'Orcia Region from Florence

9 to 10 hoursFree Cancellation

5.0

(5)

from $441

Price varies by group size

Aperitif on the Terrace of Podere Montale at Sunset

1 hourFree Cancellation

4.8

(21)

from $47

Private: Tuscany Day Tour from Rome with Optional Wine Tasting

Escape the hustle and bustle of Rome and explore the serene, UNESCO-listed Val d’Orcia with a private, customizable tour. Enjoy hotel pick-up and drop-off with an English-speaking driver in a comfortable Mercedes sedan or minivan, stopping in the charming towns of Montepulciano, Pienza, and Montalcino. Opt for a winery visit and wine tasting along the way at additional cost, or adjust the itinerary to suit your preferences.

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Private: Tuscany Day Tour from Rome with Optional Wine Tasting

10 to 11 hoursFree Cancellation

5.0

(13)

from $705

Price varies by group size

Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch

9 hoursFree Cancellation

4.5

(17)

from $815

Price varies by group size

Private Montalcino and Pienza Tour from Siena

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

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Private Montalcino and Pienza Tour from Siena

6 hoursFree Cancellation

4.0

(3)

from $549

Price varies by group size

Private Tuscany Wine Experience from Rome: Montepulciano & Pienza

Dating back to the Etruscan era, the medieval settlements of Montepulciano and UNESCO–listed Pienza are considered among Tuscany’s prettiest hilltop towns—but reaching them from Rome without your own vehicle is a challenge. On this tour, visit both towns in comfort by air-conditioned minivan and enjoy free time to explore the historic streets at your leisure. Admire uninterrupted views over the Val d'Orcia, with round-trip travel from your Rome hotel included.

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Private Tuscany Wine Experience from Rome: Montepulciano & Pienza

12 hoursFree Cancellation

5.0

(5)

from $1,763

Per group

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What are people saying about Pienza

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.

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.

Small-Group Montepulciano and Pienza Day Trip from Siena

Margaret_K, May 2026

Amazing Tuscan Tour

Chiara was an excellent driver and guide. Pienza was a magical place to visit and the farmhouse luncheon was a wonderful experience. Scenery of the Tuscan countryside was amazing. We would definitely recommend this tour.

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Kevin_L, Feb 2026

The Perfect Tuscan experience!

Exactly what we were looking for! A unique experience-. Mattea was a colorful guide, fun and knowledgeable of the area and wines. A small self sustaining cheese farm with olive oil and wine. Pienza is a must see and finally a private wine tasting in montalcino.! Thanks Mattea for a great day!

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Cynthia_P, May 2026

Great scenery and wine

Beautiful scenery and lovely wine. Second time taking this tour. The quality of the lunch has decreased since last year but the scenery is still wonderful from restaurant terrace. Wine pours seemed to be smaller and wine prices are up. Driver was diligent but parking was a challenge and we needed to walk further than last year to reach the restaurant in Pienza and the winery in Montepulciano. This was a bit of a challenge for me in 90+ F degree heat.

Small-Group Montepulciano and Pienza Day Trip from Siena

Kim_H, May 2026

Great small group Day Tour

Great trip from the minute we started. Our driver/tour guide Juliana greeted us with a smile and off we went. Her knowledge of the area and her enthusiasm for all the locations we visited was outstanding. Perfect combination of sightseeing with frequent stops along the way. The “Farm to Table lunch was a highlight for sure. Highly recommend, you will not be disappointed.

Small-Group Montepulciano and Pienza Day Trip from Siena

Cynthia_K, May 2026

U.S. Cousins

We thoroughly enjoyed Daniele on our tour of Pienza and Montepulciano. His knowledge of the area, wine making, olive oil and the native plants was wonderful. We learned a lot about the beauty of the area and saw some amazing scenery. He was there to answer all our questions with great kindness. We can’t thank him enough for sharing all this with us. Cindy, Sally and Kitty

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

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