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Home/Italy/Tuscany/Pienza

Unforgettable Pienza Travel & Wine Experiences

Immerse yourself in the breathtaking beauty of Pienza, a UNESCO World Heritage jewel nestled in the heart of the Val d'Orcia. Experience the ultimate Tuscan dream with authentic wine tasting tours, guided food adventures, and scenic walking tours through rolling hills and historic streets. Whether you are exploring the charming Renaissance architecture or savoring world-class Pecorino cheese and Brunello di Montalcino wines, Pienza offers an unforgettable escape. Book your private or group tour today to witness the most iconic landscapes of Italy and create lifelong memories in this idyllic hilltop paradise.

4.9/5 avg ratingFrom $225 per person26 unique experiences85% private tours available

At a glance

Rating

Rating

4.9★ average

Based on 1,037 pooled reviews with ~90% positive sentiment

Tour Price

Tour Price

$299–$802 typical

Median price is $579, with a full range up to $1,348

Tour Length

Tour Length

6–11.5 hours typical

Median duration is 9.5 hours

Best Value

Best Value

Walking Tours

Average 4.9★ at $430, which is at or below typical pricing

Tour Type

Tour Type

Cultural & Wine

85% are cultural themes and 73% are wine tasting tours

Flexibility

Flexibility

92% free cancellation

Most options offer flexible booking and 88% provide instant confirmation

26 Products

Small-Group Montepulciano and Pienza Day Trip from Siena

Small-Group Montepulciano and Pienza Day Trip from Siena

8 hrsFree cancellation
4.9 (312 reviews)
94.97%
5.03%
amazingviews were breathtakingknowledgeable
Viator
$224
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Small-Group Montepulciano and Pienza Day Trip from Siena
Summary

Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns...

Inclusions
  • Transport by air-conditioned minivan (maximum 8 passengers)
  • Driver/Guide
Exclusions
  • Hotel pickup and drop-off
Itinerary
  • Basilica Cateriniana Di S. Domenico
  • Historic Centre of the City of Pienza
  • Il Duomo di Pienza
  • Val D'Orcia
  • Montepulciano
  • Piazza Grande a Montepulciano
Good to know
  • Infants and small children can ride in a pram or stroller, Public transportation options are available nearby, Specialized infant seats are available, Not recommended for travelers with poor cardiovascular health, Suitable for all physical fitness levels, Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

9 hrsPrivate tourFree cancellation
4.97 (97 reviews)
99.78%
0.22%
fantasticwinegreat experience
Viator
$912
Book now
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Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano
Summary

A heaven for wine lovers: situated just south of Siena lies the land of some of the best Italian wines: Brunello di Montalcino and Nobile di Montepulciano. Based on the clones of Sangiovese, some of the most collectible and popular wines in all of Italy are produced here. Most of the tour takes pl...

Inclusions
  • Hotel pickup and drop-off
  • Private tour
  • Driver/guide
  • Live commentary on board
  • Transport by air-conditioned minivan
Exclusions
  • Lunch and wine tasting fees
Itinerary
  • Val D'Orcia
  • Montalcino
  • Piazza Grande a Montepulciano
  • Historic Centre of the City of Pienza
Good to know
  • Specialized infant seats are available, Wheelchair accessible, Infants and small children can ride in a pram or stroller, Public transportation options are available nearby, Transportation options are wheelchair accessible, Suitable for all physical fitness levels, Collapsible wheelchairs can be accommodated providing the passenger is accompanied by someone who can assist them board and disembark, Operates in all weather conditions, please dress appropriately, Vegetarian option is available, please advise at time of booking if required, Gluten free lunch option is available, please advise at time of booking
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

8 hrsPrivate tourFree cancellation
5 (36 reviews)
100%
0%
maravillosowonderful Brunello winesexcellent tour
Viator
$824
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Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour
Summary

Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive a tour of an organic dairy farm followed by a cheese tasting. Visit the beautiful Renaissance gem that is the hilltown of Pienza and enjoy lun...

Inclusions
  • Private tour
  • All taxes, fees and handling charges
  • Wine tasting
  • Driver/guide
  • Hotel pickup
  • Food tasting
Exclusions
  • Lunch
Itinerary
  • Buonconvento
  • Pienza
  • Piazza Pio II
  • Montalcino
Good to know
  • Infants and small children can ride in a pram or stroller, Service animals allowed, Specialized infant seats are available, Suitable for all physical fitness levels, May be operated by a multi-lingual guide, Vegetarian option is available, please advise at time of booking if required
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Val D'Orcia Dreaming!!

Val D'Orcia Dreaming!!

4 hrsPrivate tourFree cancellation
5 (19 reviews)
100%
0%
wonderfulexcellent tour guidelandscape
Viator
$231
Book now
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Val D'Orcia Dreaming!!
Summary

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 spok...

Itinerary
  • Historic Centre of the City of Pienza
  • Bagno Vignoni
  • Val D'Orcia
Good to know
  • Infants are required to sit on an adult’s lap, Not recommended for travelers with spinal injuries, Not recommended for travelers with poor cardiovascular health, Suitable for all physical fitness levels
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Private: Tuscany Day Tour from Rome with Optional Wine Tasting

Private: Tuscany Day Tour from Rome with Optional Wine Tasting

11 hrsPrivate tourFree cancellation
5 (13 reviews)
100%
0%
amazinghighly recommendfabulous restaurant
Viator
$705
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Private: Tuscany Day Tour from Rome with Optional Wine Tasting
Summary

With this private daytrip from Rome you will: - Stop at ancient lovely towns - Drive through the beautiful countryside of Tuscany - Visit a winery and enjoy a wine tasting (optional) - Ride on a comfortable Mercedes (sedan or minivan) - Meet the driver at your hotel - Customize the itinerary based ...

Inclusions
  • Mercedes sedan/minivan
  • Winery visit and wine tasting (optional at additional price)
  • Private driver (English speaking)
  • The itinerary can be customized based on your preferences
  • Hotel pick-up and drop-off
Exclusions
  • Tour Guide
Itinerary
  • Montepulciano
  • Piazza Grande a Montepulciano
  • Monticchiello
  • Historic Centre of the City of Pienza
  • Il Duomo di Pienza
  • Palazzo Piccolomini
  • Montalcino
  • Fortezza di Montalcino
Good to know
  • Wheelchair accessible, Infants and small children can ride in a pram or stroller, Service animals allowed, Specialized infant seats are available, Transportation options are wheelchair accessible, Suitable for all physical fitness levels, Please note that a fair amount of walking is required as the town centers are pedestrian only areas, We recommend wearing comfortable walking shoes
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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

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

9 hrsPrivate tourFree cancellationLikely to sell out
4.94 (16 reviews)
95.13%
4.87%
very beautifullovely wine tastingenjoyable day
Viator
$1,161
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Private Tour: Orcia Valley to Montalcino and Montepulciano with Brunello Wine Tasting
Summary

Spend a day exploring the wine region of the Val d'Orcia (Orcia Valley) with this full-day private tour from Florence. With your private group of no more than 7 passengers in the vehicle, you'll visit Montalcino, Montepulciano, and take in the scenery of the Orcia Valley. Enjoy a Brunello di Montalc...

Inclusions
  • Hotel pickup and drop-off
  • Private tour
  • Transport by air-conditioned minivan
Exclusions
  • Food and drinks
  • Lunch
  • Wine tasting
Itinerary
  • Piazza Grande a Montepulciano
  • Historic Centre of the City of Pienza
  • Val D'Orcia
  • Montalcino
Good to know
  • Infants and small children can ride in a pram or stroller, Public transportation options are available nearby, Specialized infant seats are available, Suitable for all physical fitness levels, Please advise any specific dietary requirements at time of booking
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

10.5 hrsFree cancellation
4.67 (386 reviews)
84.49%
15.51%
excellent wineamazingfood
Viator
$269
Book now
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Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano
Summary

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 we cannot gua...

Inclusions
  • 2 Wine Tastings
  • Local product food tasting during the wine tasting in Montepulciano
  • Guided tour on vineyard and barrel cellar
  • Premium van with A/C
  • Superior Lunch with stunning view (November to April we cannot guarantee the restaurant with view)
  • English-speaking driver (driver is not the guide)
  • Guided tour on the underground city of Montepulciano
Exclusions
  • Private Pick-Up
Itinerary
  • Florence
  • Montalcino
  • Fortezza di Montalcino
  • Historic Centre of the City of Pienza
  • Montepulciano
  • Florence
Good to know
  • Infants and small children can ride in a pram or stroller, Public transportation options are available nearby, Specialized infant seats are available, Suitable for all physical fitness levels
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Montepulciano Wine and Pienza Flavours Private Day Tour from Rome

Montepulciano Wine and Pienza Flavours Private Day Tour from Rome

10 hrsPrivate tourFree cancellation
4.85 (33 reviews)
97.01%
2.99%
excellentgreat wineexcellent experience
Viator
$423
Book now
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Montepulciano Wine and Pienza Flavours Private Day Tour from Rome
Summary

Our years of experience have allowed us to prepare this special tour to Montepulciano & Pienza for those who love Italian wine and food. Thanks to our high quality state of mind we will chauffered you there from Rome in a luxurious Mercedes Benz Minivan, in a completely private tour! And of course...

Inclusions
  • English Speaking Driver for the length of the service
  • Courtesy and service
Exclusions
  • Tickets to enter the Sites
  • Private Licensed Tour Guides
Itinerary
  • Val D'Orcia
  • Centro storico
  • Centro storico
  • Historic Centre of the City of Pienza
Good to know
  • Wheelchair accessible, Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Specialized infant seats are available, Transportation options are wheelchair accessible, Suitable for all physical fitness levels
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Medieval Tour in Monteriggioni and Val d'Orcia from Florence

Medieval Tour in Monteriggioni and Val d'Orcia from Florence

11 hrsFree cancellation
4.77 (70 reviews)
85.35%
14.65%
very goodexperienciarecomendaría
Viator
$51
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Medieval Tour in Monteriggioni and Val d'Orcia from Florence
Summary

Our first stop is Pienza, a charming Renaissance village located in the heart of the Val d'Orcia. Famous worldwide for its delicious Pecorino di Pienza, this stop is the perfect opportunity to stroll through picturesque streets and taste one of Tuscany’s most iconic cheeses. After visiting Pienza, ...

Inclusions
  • Transportation by bus with air-conditioned
  • Wi-Fi on board the bus
  • Expert multilingual escort (not for Transfer Only)
  • Access to the medieval walls in Monteriggioni (not for Transfer Only)
  • Tasting of 1 Brunello di Montalcino + 1 Rosso di Montalcino + cold cuts and cheeses (if selected)
  • Entrance ticket to the Templar Museum (not for Transfer Only)
  • Tasting in Monteriggioni of 3 local wines with olive oil and typical products(not for Transfer Only)
Exclusions
  • Meals
  • Pick up service at the hotel
  • anything that is not specifically present in the "Included Services" list
Itinerary
  • Pienza
  • Il Duomo di Pienza
  • Piazza Pio II
  • Palazzo Piccolomini
  • Montalcino
  • Fortezza di Montalcino
  • Palazzo dei Priori
  • Monteriggioni
Good to know
  • Infants and small children can ride in a pram or stroller, Public transportation options are available nearby, Infants are required to sit on an adult’s lap, Not recommended for travelers with spinal injuries, Travelers should have at least a moderate level of physical fitness, order of visits may change, In order to reserve the seat also for children under 4 years of age, it is necessary to select the free rate 'children (0 - 3)' during the purchase phase., The tour involves walking, it is recommended to wear comfortable shoes, the tasting of wine with typical products is not a lunch, Transfer time on board bus is already included in the total duration, No refunds are given in case of delay at the meeting point at Sightseeing Experience Visitor Center, Maximum punctuality is recommended at each meeting points during the excursion. For the success of the tour, no waiting times are expected in case of delays by ustomers and no refunds will be granted, The order of visits may change, Transfer Only option includes only bus and assistance on board.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch

Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch

9 hrsPrivate tourFree cancellation
4.53 (17 reviews)
85.54%
14.46%
excellentlunch and wine tastingfun
Viator
$815
Book now
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Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch
Summary

Revel in Tuscany’s wine country and hilltop towns on this Privateday trip from Florence. Traveling by luxury minivan with an expert driver-escort, explore the idyllic hill-towns of Montepulciano and Pienza, learn about Pecorino Cheese in a local dairy and taste this delicious local produce. In Pienz...

Inclusions
  • Visit Montepulciano & Pienza
  • Expert English speaking driver-escort
  • Transport by air-conditioned Mercedes minivan
  • Pecorino Cheese Tasting at local dairy
Itinerary
  • Piazza della Repubblica
  • Historic Centre of the City of Pienza
Good to know
  • Public transportation options are available nearby, Specialized infant seats are available, Travelers should have at least a moderate level of physical fitness, Comfortable shoes are recommended, Appropriate dress is required to enter some sites - knees and shoulders must be covered, Minimum drinking age is 18 years, Children must be accompanied by an adult, Infant seats are available on request if advised at time of booking (children who are under 36 kg/97 pounds or 150 cm/4ft 9 in,must use proper child restraints). We reserve the right to refuse infants or children if we are not notified at the time of the booking and if the car seats brought do not comply with requirements by Italian law., Operates in all weather conditions, please dress appropriately, Minimum numbers apply. There is a possibility of cancellation after confirmation if there is not enough passengers to meet requirements. In the event of this occurring, you will be offered an alternative or full refund, All passengers pay the same rate irrespectively from their age
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Pairs well with

Landmarks travelers visit on the same route as Pienza.

Siena Historic Center (Siena Centro Storico)
Learn more

Siena Historic Center (Siena Centro Storico)

200 m away • from $26

Val d'Orcia
Learn more

Val d'Orcia

5.2 km away • from $92

Temple of San Biagio (Tempio di San Biagio)
Learn more

Temple of San Biagio (Tempio di San Biagio)

8.0 km away • from $7

Terme di Saturnia
Learn more

Terme di Saturnia

50 km away • from $91

Frequently Asked Questions

Get answers to the most common questions travelers ask before visiting.

Wine tasting tours dominate the options we compare, representing 73% of all tours across booking platforms. Food tours are the next most common at 35%, followed by walking tours (27%), sightseeing tours (19%), and day trips (15%). Most tours blend multiple themes: 85% are cultural experiences, while 73% include food and drinks, and 38% focus on history. This means you'll typically encounter knowledgeable guides exploring Pienza's Renaissance architecture, local cuisine, and wine heritage together rather than in isolation.

Tours across the platforms we compare range widely, from $226 to $1,348, with most falling in the $299–$802 band and a median price of $579. This spread reflects different tour lengths, group sizes, and inclusions. Walking tours offer particularly strong value: they average $430 and maintain a 4.9-star rating, placing them at or below the typical price while matching the overall quality standard.

85% of the options we compare are private tours, making one-on-one or small-group experiences the dominant format. This high proportion means you'll have flexibility in pacing, route adjustments, and personalized attention. If you prefer a larger group setting, group tours do exist but represent a smaller share of available options.

Inclusion varies by tour, but across the options we compare: 62% include a professional guide, 35% offer hotel pickup and drop-off, 31% feature wine tasting, and 27% provide either a dedicated driver or transport. Most tours get around by car (38% of options) or minivan (27%), so you're rarely walking the entire time unless you book a dedicated walking tour. Check the specific listing for what matters most to you, since inclusions are customizable on many private tours.

Tours typically last 6 to 11.5 hours, with a median of around 9.5 hours, giving you a full immersion in the region's culture, food, and wine. Language options span 7 languages across the tours we compare: English, Italian, Spanish, French, Chinese, German, and Portuguese. Most tours are offered in English and Italian, so check your preferred language when booking.

Reviews are overwhelmingly positive, with an average rating of 4.9 stars across 1,037 combined reviews from booking platforms. Reviewers repeatedly highlight the wine, food, views, and knowledgeable guides, using words like "wonderful," "amazing," and "excellent." Around 90% of reviews are positive, reflecting consistently strong experiences across the tours we compare.

Booking ahead is worth considering: 12% of options are flagged as likely to sell out, particularly popular time slots. The good news is that 92% of tours offer free cancellation, giving you flexibility if your plans shift. Additionally, 88% provide instant confirmation, so you can often secure your spot immediately. This combination of cancellation policies and instant booking means you can reserve with confidence.

A small number of tours across the platforms we compare are tagged as eco-friendly (12%), though these tags are applied loosely and don't imply formal certification. Walking tours are more readily available at 27% of options and offer excellent value at an average of $430 with a 4.9-star rating. If sustainability or a slower pace appeals to you, mention these priorities when filtering or contacting tour operators directly.

From Florence, take a train to Montepulciano, then a bus to Pienza (2-3 hours total). From Rome, drive or take a bus to the Val d'Orcia region. Car rental offers flexibility for exploring nearby towns.

Yes, the town center is walkable but features steep cobblestone streets and stairs. Wear comfortable shoes with good grip. The historic center is compact, taking 1-2 hours to explore thoroughly.

Try pecorino cheese (the town's signature), pici pasta, and local wines. Visit family-run trattorias in the main piazza. Book ahead during peak season as restaurants fill quickly with tour groups.

Val d'Orcia5.2kmTemple of San Biagio (Tempio di San Biagio)8kmMontalcino Fortress (Fortezza di Montalcino)15.4kmMontalcino15.5kmAbbey of Sant'Antimo (Abbazia di Sant'Antimo)15.8kmSanta Margherita Basilica (Basilica di Santa Margherita)33.8kmLake Trasimeno (Lago Trasimeno)34.5kmSiena Piazza del Mercato38.6kmPubblico Palace (Palazzo Pubblico)38.7kmMangia Tower (Torre del Mangia)38.7kmSiena Civic Museum (Museo Civico di Siena)38.7km