Recent Searches
Clear

Travel update: We’re doing our best to help keep you safe and your plans flexible. Learn more.

Read More

Pienza Tours

star-5
19 Reviews
Pienza
UNESCO-listed Pienza was little more than a sleepy hamlet until the reign of Pope Pius II in the first half of the fifteenth century. Pienza, then called Corsignano, was the pope’s home town, and he enlisted the help of architect Bernardo Rossellino to transform the village into an ideal Renaissance town. The reconstruction began in 1459 and only lasted four years, but the result has put Pienza on the radar of many a traveler to Tuscany.

The town’s historic center offers excellent examples of Renaissance architecture, particularly the cathedral, Palazzo Piccolomimi and Palazzo Borgia, all flanking charming Piazza Pio II. While it’s easy to breeze through the tiny town — it only takes five minutes to walk from one side to the other — it’s also an inviting place to savor a local specialty, sheep’s milk pecorino cheese with a bit of honey drizzled over the top.

Practical Info

Pienza can get extremely crowded on summer weekends, so if possible, plan your visit for a weekday or shoulder season.
Address: Pienza, Tuscany, Italy, Italy
Read More

35 Tours and Activities to Experience Pienza

Filter
Select Dates
Today
Tomorrow




Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details
Sort by:Featured
Montalcino, Orcia Valley, Pienza, and Montepulciano: Wine- and Cheese-Tasting Guided Tour from Florence

Montalcino, Orcia Valley, Pienza, and Montepulciano: Wine- and Cheese-Tasting Guided Tour from Florence

star-4.5
Discover some of the highlights of Tuscany on this day trip from Florence by coach. Visit historical hill towns Pienza, Montalcino, and Montepulciano; admire the gorgeous, vineyard-covered scenery of Orcia Valley (Val d’Orcia); and enjoy cheese and wine tastings as you stop at local wineries and other venues. It’s a great day out in the Italian countryside.
More
  • 11 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$83.27
From
$83.27
Taking safety measures

Small-Group Montepulciano and Pienza Day Trip from Siena

Small-Group Montepulciano and Pienza Day Trip from Siena

star-4.5
Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. 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 an optional visit to a winery. Group size is limited to eight people, ensuring personalized attention from your guide.
More
  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$166.55
From
$166.55
Taking safety measures

Tuscan Food and Wine Tour of Val d'Orcia from Florence

Tuscan Food and Wine Tour of Val d'Orcia from Florence

star-4
Experience the sights and flavors of Tuscany on a full-day tour from Florence that takes you through the Val d'Orcia region to the elegant Renaissance architecture of Montepulciano. Explore the history of Montalcino’s imposing fortress and the jewel-box village of Pienza, savoring the bounty of the Val d’Orcia region with tastings of local wines and specialty foods along the way.
More
  • 12 hours
  • Free Cancellation
  • Taking safety measures
From
$83.27
From
$83.27
Taking safety measures

Full-Day Winery Tour in Montepulciano with Tasting and Lunch

Full-Day Winery Tour in Montepulciano with Tasting and Lunch

star-5
Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Brunello. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.
More
  • 1 to 8 hours
  • Free Cancellation
From
$277.04
Price varies by group size
From
$277.04
Price varies by group size

Brunello and Nobile Wine Lovers' Tour: Montalcino and Montepulciano

Brunello and Nobile Wine Lovers' Tour: Montalcino and Montepulciano

star-5
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 for a gourmet lunch and tasting of famed Brunello di Montalcino wine. Continue through Tuscany’s World Heritage-listed Val d’Orcia region to reach Montepulciano, known for its Nobile di Montepulciano wine, and taste this prized elixir at a winery. Learn about the area’s history and winemaking heritage from a private guide, and meet local producers for an immersive tasting experience. Price is per group, with a maximum of either three or eight passengers, depending on season and vehicle type.
More
  • 9 hours
  • Free Cancellation
  • Taking safety measures
From
$668.45
per group
From
$668.45
per group
Taking safety measures

From Siena: Pienza and Montepulciano Wine Tour

From Siena: Pienza and Montepulciano Wine Tour

star-4.5
Taste your way through Tuscany with this full-day wine tour of Montalcino, Pienza, and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano and Montalcino.
More
  • 9 hours
  • Free Cancellation
  • Taking safety measures
From
$65.43
From
$65.43
Taking safety measures

Val d'Orcia private tour: Montalcino, Pienza and Montepulciano

Val d'Orcia private tour: Montalcino, Pienza and Montepulciano

star-5
Experience the heart of Tuscany by visiting the enchanting Val D’Orcia led by your private driver. Let your personal chauffeur do all the work and take you on a journey through the spellbinding Val D'Orcia countryside, a region known for its scenic beauty, picturesque villages, rolling hills and cypresses! Explore in total freedom the enchanting towns of Montalcino, Pienza and Montepulciano and savour the best wines in the world! The first stop will be Montalcino, land of the world-renowned Brunello wine, a labyrinth of cobbled streets, quaint wine shops and Romanesque-style churches. The following stop is Pienza, which stands high upon a hill and dominates all the Orcia valley with extraordinary views. The last stop reaches Montepulciano, home to the famous Vino Nobile vineyards and more recently famous for the filming of the vampire movie "New Moon". Enjoy your free time in the most elegant village of the entire Val D'Orcia.
More
  • 9 hours
  • Free Cancellation
  • Taking safety measures
From
$392.57
Price varies by group size
From
$392.57
Price varies by group size
Taking safety measures

Private market tour, lunch or dinner and cooking demo in Pienza

Private market tour, lunch or dinner and cooking demo in Pienza

Dive into the Italian way of life by living just like the locals do. Visit the vibrant local market and immerse yourself in a private dining experience at a Cesarina's home, enjoy an exclusive cooking demo and taste authentic local recipes treasured in family cookbooks passed down by real Italian Mammas. Feel the warmth of Italian hospitality as you connect with local people. Enjoy a 4-course menu including starter, pasta, main course with side dish, dessert with drinks included (water, selection of red and white wines from regional cellars and coffee). At the end of the experience, take your souvenir back home: the official Cesarine apron and shopping bag.
More
  • 4 hours
  • Free Cancellation
From
$172.49
From
$172.49

Brunello and Nobile Wine Tour from Florence

Brunello and Nobile Wine Tour from Florence

Discover the natural beauty of Italy's Val d'Orcia on this private tour that introduces you to the postcard-perfect scenery of rolling hills and vineyards. You'll visit the towns of Montepulciano, Pienza, and Montalcino; tour a winery; and enjoy included wine tastings and a Tuscan lunch for a well-rounded experience in this UNESCO World Heritage–listed valley.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$475.85
Price varies by group size
From
$475.85
Price varies by group size
Taking safety measures

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

star-5
Leave the planning and driving to someone else on this daylong winery tour specializing in Brunello di Montalcino—a wine produced in the vineyards around the town of Montalcino. Visit historic wine cellars and vineyards, have lunch in a winery in the hill town of Montalcino itself, and visit a winery in the nearby Nobile di Montepulciano area for good measure.
More
  • 1 to 8 hours
  • Free Cancellation
From
$272.42
Price varies by group size
From
$272.42
Price varies by group size

Poetic Valdorcia

Poetic Valdorcia

The Valdorcia Valley is the most iconic image of Tuscany all over the world. It is recognised as World Heritage Site by UNESCO. Discover this masterpiece of nature and human labour with our slow-paced tour that will let you enjoy its treasures. Galavent through the small lanes of Pienza, a town designed according to the Renaissance canons of beauty. Chill out in the Medicean gardens of dormant San Quirico d’Orcia and enjoy the views over gentle hills dotted with medieval hamlets, cypress and olive trees. Let ancient villas and churches invite you to day-dream. Valdorcia is a landscape symphony that will touch your heart. Fearing an aesthetic overload? No worries, delicious food is also part of this tour: Pienza is well known for its fantastic pecorino cheese! We will finish our tour in Bagno Vignoni, a unique hamlet where an ancient source of thermal water springs out right in the middle of the local piazza. A short stay in one of the local SPAs can be arranged upon request!
More
  • 7 hours
  • Taking safety measures
From
$219.53
From
$219.53
Taking safety measures

Montalcino and Montepulciano Private Tour

Montalcino and Montepulciano Private Tour

star-5
Explore the beautiful Val d’Orcia just outside of Florence on this private full-day tour. Drive through the rolling countryside to visit the picturesque towns of Montepulciano, Pienza, and Montalcino. Sample wines from local vineyards and sit down to a delicious lunch made with fresh ingredients from the region. Discover the Tuscany that appears in movies and on postcards during this tour and admire the beautiful landscapes.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$452.05
Price varies by group size
From
$452.05
Price varies by group size
Taking safety measures

Private Montalcino and Montepulciano Tour from Siena

Private Montalcino and Montepulciano Tour from Siena

Travelling in Val d'Orcia is an unforgettable experience. Your eyes become dazzled by the beauty of the colours of this land, unsurprisingly a UNESCO World Heritage Site. This tour has been created for you to discover the most painted corner of Tuscany, made of enchanted landscapes, tree-lined avenues. Sunrises and sunsets of extraordinary, unique colours in the world are one great addition when wandering the road from Montepulciano to Montalcino through Pienza, considered one of the most amazing routes of Italy.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$428.26
Price varies by group size
From
$428.26
Price varies by group size
Taking safety measures

Montalcino and Pienza, The Dream land

Montalcino and Pienza, The Dream land

Experience the real Tuscan essence by visiting the Orcia Valley and its beautiful villages! Meet you guide in Montalcino, where the world-famous Brunello wine is produced! Wonder through the Medieval twisty streets and explore the Fortress, whose design became a model for all the Tuscan cities, the “Chiesa dei Senesi” and then head to the square housing the “Palazzo Comunale”; learn about the history of the village and its importance. Take a walk to the Cathedral for an amazing view on the valley surrounding Montalcino and stop for a glass of the celebrated Brunello before heading to Pienza! After a scenic drive through the vineyards, you will arrive in the heart of the Orcia! Pienza it’s a real and unexpected Renaissance jewel. Enjoy the artistic beauty by discovering the Cathedral as well as the Piccolomini Palace, once home to the Pope Pius II, among many other architectural jewels. Walk along the city walls for a breathtaking view and a tasting of the famous pecorino cheese.
More
  • 6 hours
From
$661.82
Price varies by group size
From
$661.82
Price varies by group size

Montepulciano and Pienza Tuscany Wine&Cheese Fullday from Florence

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 tour guide included in Private option. Private or Shared Tour available options. 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
More
  • 10 hours
  • Free Cancellation
  • Taking safety measures
From
$315.25
Price varies by group size
From
$315.25
Price varies by group size
Taking safety measures

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

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

Grand tour of the Val D'Orcia allows you to discover the most beautiful Tuscan countryside with a Professional Tour Guide-Sommelier The small towns of Montalcino, Pienza and Montepulciano are the essence of this region, the dream of every curious traveler and lover of art, good food and great wines. Discover the splendid Renaissance town of Montepulciano, its splendid square, surrounded by magnificent palaces from the 1500s, its extraordinary underground medieval cellars, the elegant streets with small shops and artisan shops and wine bars. Be in love with Pienza, a UNESCO site, the charming village created by Pope Pius II, the extraordinary Renaissance cathedral, and the incredible view over the valley. Tasting of the delicious pecorino cheese. Visit the famous wine town of Montalcino and taste the celebrated Brunello di Montalcino wine in a winery. *** Trasportation is not included *you need of your own car for this tour. *I have my car I dont need to travel with you
More
  • 8 hours
  • Free Cancellation
From
$427.05
per group
From
$427.05
per group

Montepulciano Wine & Pienza Flavors Day Tour from Rome

Montepulciano Wine & Pienza Flavors Day Tour from Rome

star-5
For those who love Italian wine and food. Thanks for the luxurious Mercedes Benz Minivan, in a completely private tour! Is also incredible knowledgeable about Italy and will have to be ready to answer anyway and give you interesting tips along the way! In addition, it´s also good to highlight we know to make this experience super value one!
More
  • 10 hours
  • Free Cancellation
From
$444.30
Price varies by group size
From
$444.30
Price varies by group size

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

star-5
Experience the best of Tuscany—cheese and wine, of course!—on this private tour from Siena. You’ll admire fabulous scenery in the Val d’Orcia, learn about cheese making during a tour at an organic dairy farm, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine during a cellar tour at a winery in the hilltop town of Montalcino. With a privately guided tour, enjoy a more personalized experience.
More
  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$843.33
per group
From
$843.33
per group
Taking safety measures

Tuscany Semi Private Day Tour with Wine and Cheese Tasting

Tuscany Semi Private Day Tour with Wine and Cheese Tasting

star-4.5
Discover Tuscany’s renowned wine country on a day trip from Florence with a small group. Led by a driver-tour escort, venture to the town of Montepulciano by minivan and stop at a rustic wine cellar to taste the area’s vino di nobile blends. Then head to Montalcino to sample three Brunello di Montalcino wines. Top off your day with a stroll to Pienza, a beautiful Renaissance hill town and home to the famous Pienza Pecorino cheese. Numbers are limited to eight people to keep this experience as intimate as possible.
More
  • 10 hours
  • Free Cancellation
  • Taking safety measures
From
$403.28
From
$403.28
Taking safety measures

Montalcino and Montepulciano Tour from Florence

Montalcino and Montepulciano Tour from Florence

star-5
Travel through the Val d'Orcia region of Tuscany with the benefit of your own private guide on this full-day tour from Florence. Receive personalized attention as you visit picturesque towns including Montepulciano, Pienza, and Montalcino. Stop into a winery, go wine tasting, and stroll through streets lined with centuries-old buildings in a region that has been designated a UNESCO World Heritage Site.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$499.64
Price varies by group size
From
$499.64
Price varies by group size
Taking safety measures

Tuscany Tour in English from Siena

Tuscany Tour in English from Siena

Benefit from a private full-day tour of Tuscany with round-trip transportation from Siena. Have free time during your visits to Montalcino, Pienza, and Montepulciano, and have the option to stop for lunch, and wine or cheese tastings in the countryside. Travel in comfort in an air-conditioned private vehicle with hotel pickup and drop-off included.
More
  • 8 to 9 hours
  • Free Cancellation
From
$1,062.45
per group
From
$1,062.45
per group

Wine Cheese and EVO Oil Tastings Southern Tuscany Fullday from Florence

Wine Cheese and EVO Oil Tastings Southern Tuscany Fullday from Florence

Experience this great FullDay Tour from Florence exploring the Southern Tuscany towns and countryside and see: • Montepulciano • Pienza • Chianciano Included: - Wine Tasting - Pecorino Cheese Tasting - EVO Oil Tasting Local tour guide included in Private option. Pickup and dropoff your accommodation. Private or Shared Tour available options. 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
More
  • 10 hours
  • Free Cancellation
  • Taking safety measures
From
$315.25
Price varies by group size
From
$315.25
Price varies by group size
Taking safety measures

Val D'Orcia Dreaming!!

Val D'Orcia Dreaming!!

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!!!!!
More
  • 4 hours
  • Free Cancellation
From
$214.13
From
$214.13

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

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

star-5
Taste your way through some of Tuscany’s finest wine regions and most charming medieval villages on this private, full-day tour from Florence. Drive through the scenic Orcia Valley and visit the birthplaces of prized Brunello di Montalcino and Nobile di Montepulciano red wines. Whether you want to explore the medieval villages, tour historic wine cellars and vineyards or savor a farm-fresh lunch, a private driver and guide will customize the itinerary to create a perfect day in the Tuscan countryside. Price is per group, based on a maximum of 7 passengers per vehicle.
More
  • 9 hours
  • Free Cancellation
From
$911.66
per group
From
$911.66
per group

Frequently Asked Questions