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Home/Italy/Tuscany/Siena/Montalcino

Experience Authentic Montalcino Wine & Culture

Immerse yourself in the rolling hills of the Val d'Orcia with an unforgettable journey to Montalcino. As a jewel of the Tuscan countryside and a UNESCO World Heritage region, Montalcino invites you to indulge in world-class Brunello di Montalcino wine tastings, authentic food tours, and breathtaking sightseeing adventures. Whether you are exploring historic hilltop fortresses on a guided walking tour or enjoying a private wine experience, our curated selection of 87 top-rated activities ensures a perfect escape. Discover the soul of Italy through its rich culture, stunning landscapes, and unparalleled culinary traditions. Book your Tuscan dream today!

4.8/5 avg rating87 unique experiencesFrom $78 per person85% free cancellation

At a glance

Tour Price

Tour Price

$162–$696 typical

Median price is $323, with a full range of $79–$1,216

Rating

Rating

4.82★ average

Based on 4,010 pooled reviews with ~90% positive sentiment

Tour Length

Tour Length

5–11 hours typical

Median duration is 9 hours

Best For

Best For

Wine & Food

83% are wine tasting tours and 84% focus on food and drinks

Tour Style

Tour Style

51% private tours

79% of options are guided, with 85% offering free cancellation

Languages

Languages

8 languages offered

Includes English, Italian, Spanish, French, Portuguese, Chinese, German, and Korean

93 Products

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines

11.5 hrsFree cancellation
4.71 (1,319 reviews)
82.2%
17.8%
BreathtakingGood tripThe wine tasting was fun!
Viator
$92
Book now
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Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines
Summary

Enjoy a rich and ripe tour through the worlds of grape and gourmet cheese. Experience art and architecture and blend it with good wines and mouth-warming specialties. You will visit the stunning Val d'Orcia and the very special towns snuggling in it. There's the chance to get to know wine cellars wh...

Inclusions
  • Visit to a winery in Montepulciano with tasting of the famous “Vino Nobile" and cheese pairing
  • Visit to a wine cellar in Montalcino with tasting of the world-famous Brunello wine
  • Expert multilingual Tour Leader
  • Free time in Montalcino, Pienza and Montepulciano
  • Journey by fully-fitted GT Coach with Free Wifi on board
  • Interactive audio guide for Chinese, Korean, and Japanese
Exclusions
  • Lunch
  • Hotel pickup and drop-off
  • Attractions tickets not included in the product
Itinerary
  • Val D'Orcia
  • Montalcino
  • Fortezza di Montalcino
  • Pienza
  • Il Duomo di Pienza
  • Cappella Madonna di Vitaleta
  • Montepulciano
  • Florence
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, Specialized infant seats are available, Not recommended for travelers with poor cardiovascular health, Travelers should have at least a moderate level of physical fitness, Minimum drinking age is 18 years, May be operated by a multi-lingual guide, Please advise any specific dietary requirements at time of booking, Vegetarian option is available, please advise at time of booking if required, Please show up 20 minutes before the tour departure, English and Spanish are always guaranteed. In order to confirm the excursion in Italian, German, Portuguese or French a minimum of 4 pax is required, The order of the visits may change and Montepulciano could be the first stop, If you select Chinese, Korean, or Japanese, the historical explanations and tour commentary will be provided exclusively via audio guide (via App) in your chosen language. You will not be left alone: a professional Tour Leader will accompany the group throughout the trip. The Tour Leader will manage the group and provide logistics, meeting point details, and emergency assistance in English, while the cultural insights will be delivered via the app in your language. The wine tastings will be conducted in English. However, the app will provide additional information about the local wine in the selected native language., Disinfected radio units will be provided, and headphones will be single-use. Showing your voucher on your phone will be enough; it is not necessary to print it out.
Cancellation Policy

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

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

9 hrs
4.91 (437 reviews)
GetYourGuide
$219
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From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch
Summary

Tour the Montalcino hill, visit the town and three different Brunello wine producing wineries. Tour cellars, meet the producers, enjoy wine tastings and a winery lunch with wine.

Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

1.5 hrsFree cancellation
5 (91 reviews)
100%
0%
truly incrediblehighly recommendsublime experience
Viator
$82
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Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting
Summary

Tuscany’s Most Popular Olive Oil Tour – Discover a World-Renowned Producer Step inside one of Tuscany’s most celebrated olive oil mills and discover the secrets of world-class Extra Virgin Olive Oil. This 1.5-hour immersive experience includes: a short historical introduction, a visit to our state-...

Good to know
  • Wheelchair accessible, Infants and small children can ride in a pram or stroller, Service animals allowed, Infants are required to sit on an adult’s lap, Specialized infant seats are available, Transportation options are wheelchair accessible, All areas and surfaces 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.

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 Brunello Wine Safari and Val d'Orcia Tour from Florence

Private Brunello Wine Safari and Val d'Orcia Tour from Florence

11 hrsFree cancellation
4.98 (82 reviews)
Viator
$682
Book now
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Private Brunello Wine Safari and Val d'Orcia Tour from Florence
Summary

Hop aboard our rugged offroad vehicle and experience Tuscany like never before, surrounded by cypress-lined hills, vineyards, and medieval towns. Your adventure kicks off in Montalcino, home of the iconic Brunello. Visit a charming, family-run winery, explore its cellars, and enjoy a guided tasting...

Inclusions
  • Traditional Tuscan lunch in the historic village of Bagno Vignoni
  • Local expert guide for the duration of the tour
  • Offroad transportation along Tuscany dirt roads in our customized 4x4 coach
  • Visit to a family-run winery in Montalcino with cellar tour and Brunello di Montalcino wine tasting
  • Visit to a family-owned winery in Montepulciano with Vino Nobile di Montepulciano wine tasting
  • Free time in Pienza to explore the town, shops, and enjoy panoramic views
Itinerary
  • Florence
  • Montalcino
  • Bagno Vignoni
  • Pienza
  • Montepulciano
  • Florence
Good to know
  • Public transportation options are available nearby, Infants are required to sit on an adult’s lap, Not recommended for travelers with spinal injuries, Not recommended for pregnant travelers, Not recommended for travelers with poor cardiovascular health, Travelers should have at least a moderate level of physical fitness, Due to uneven and steep surfaces, we are unable to accept anyone with walking difficulties or wheelchair user, We regret that vegetarian or other alternative dietary requirements cannot be catered for
Cancellation Policy

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

VIP Brunello Montalcino, Montepulciano & Val d'Orcia with Lunch

VIP Brunello Montalcino, Montepulciano & Val d'Orcia with Lunch

10 hrsFree cancellationLikely to sell out
5 (45 reviews)
99.19%
0.81%
loved the winesexcellentbreathtaking
Viator
$253
Book now
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VIP Brunello Montalcino, Montepulciano & Val d'Orcia with Lunch
Summary

This is an experience for true wine lovers, selecting the best boutique wineries including a guided lunch and wine tasting of Brunello di Montalcino, listed as one of the best wines in the world by the prestigious magazine Wine Spectator. All this while visiting 3 UNESCO's site and the famous Gladia...

Inclusions
  • Organic food, Pecorino cheese & Extra-virgin Olive oil
  • Licensed Tour Guide all day
  • Small group max 6 people
  • Wine cellars visit
  • Nobile di Montepulciano wine (only adding a 2nd winery)
  • Photo Service
Itinerary
  • Monteriggioni
  • Montalcino
  • Val D'Orcia
  • Montepulciano
Good to know
  • Infants and small children can ride in a pram or stroller, Infants are required to sit on an adult’s lap, Suitable for all physical fitness levels
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
Book now
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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.

VIP Chianti, Brunello wine & Pienza with lunch From Siena

VIP Chianti, Brunello wine & Pienza with lunch From Siena

9 hrsFree cancellationLikely to sell out
5 (28 reviews)
98.43%
1.57%
AMAZINGAMAZING TOURlovely wine tastings
Viator
$277
Book now
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VIP Chianti, Brunello wine & Pienza with lunch From Siena
Summary

This is a semi- private with maximum 6 people in tour so you will have all the attention you need. This tours will give you the advantages to truly enjoy the experience and not have to be in a crowded bus and follow a strict schedule . We will visit 2 beautiful boutique family owned wineries in a ...

Inclusions
  • Organic Balsamic vinegar & Extra virgin Olive oil tastings
  • Small group max 6 people
  • Tour of 2 wineries historical cellars
  • Licensed tour guide
  • Brunello di Montalcino, Super tuscans, Chianti Classico & Rosè wines
Exclusions
  • Museums tickets
Itinerary
  • Siena
  • Castellina In Chianti
  • Montalcino
  • Val D'Orcia
  • Pienza
Good to know
  • Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Not recommended for travelers with spinal injuries, Not recommended for pregnant travelers, Not recommended for travelers with poor cardiovascular health, Travelers should have at least a moderate level of physical fitness, This tour has been upgraded for 2025 so the reviews may be different from description.
Cancellation Policy

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

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

10 hrsPrivate tourFree cancellationLikely to sell out
5 (18 reviews)
98.05%
1.95%
greatWineriesFantastic Experience
Viator
$588
Book now
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Private Top Brunello Montalcino Wine Tour & Food Pairing Session
Summary

ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This tour includes a visit to all the three wineries to enjoy the cellars and to learn more about the wine making process from scratch. Duration of the c...

Inclusions
  • Hotel pickup and drop-off
  • All taxes, fees and handling charges
  • Driver/guide
  • Transportation in air conditioned Mercedes
  • Strictly private tour
  • Full lunch based on local products for wine pairing
  • Wine tastings fees at 3 wineries
Itinerary
  • Florence
  • Asciano
  • Montalcino
Good to know
  • Public transportation options are available nearby, Not recommended for pregnant travelers, Suitable for all physical fitness levels, Dress code is smart casual, Please advise any specific dietary requirements at time of booking, Vegetarian or vegan options available, please request in the notes at the time of booking, Minimum drinking age 18 years, Drinking alcohol inside the vehicles is not allowed, Breakfast before the tour is recommended
Cancellation Policy

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

PRIVATE Full-Day Brunello Wine with lunch from Florence

PRIVATE Full-Day Brunello Wine with lunch from Florence

9 hrsPrivate tourFree cancellation
5 (19 reviews)
100%
0%
amazingfunamazing wineries
Viator
$423
Book now
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PRIVATE Full-Day Brunello Wine with lunch from Florence
Summary

• EXPERIENCE FOR YOUR PRIVATE GROUP • Wine lovers, dedicate a day to the legendary Brunello! Embark on an extraordinary 9-hour guided tour from Florence. Travel in a luxury minivan through rolling green hills and historic vineyards, with a private driver at your disposal throughout the day. You will...

Inclusions
  • Pick-up and drop off at your selected hotel/location (Florence Down Town)
  • English-speaking licensed driver
  • On-Board WiFi
  • Private transportation by Mercedes Minivan Air-Conditioned
  • Unlimited cold mineral water
Exclusions
  • Lunch in Enoteca (to be paid on-site)
  • Wine tasting (to be paid on site, from 30€pp to 60€pp)
Itinerary
  • La Fornace
  • Montalcino
  • Enoteca la Fortezza di Montalcino
  • Paradiso di Cacuci Winery
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, Departure is suggest at 9:00am., A confirmation is appreciated the day before the appointment by e-mailing or via iMessage or WhatsApp., In case of rain, the umbrellas will be provided by your driver., This tour/experience is for a maximum of 7 travelers (your private party). Should your group exceed this size, you can make two reservations.), You will be picked up directly at your hotel or address (Florence down Town) provided at the time of booking at the exact time of the start of the tour., Upon request, during the reservation we can organize lunch in wine cellars or on farms, this is a highly recommended experience, especially for wine lovers. (They also offer vegetarian and gluten-free lunches, and accommodate allergies. Upon request 24hrs before the tour)., Minors under the age of 18 are not allowed to drink alcohol (wine tasting)., This is a private tour/activity. Only your group will participate.
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 Montalcino.

Montalcino Fortress (Fortezza di Montalcino)
Learn more

Montalcino Fortress (Fortezza di Montalcino)

100 m away • from $140

Val d'Orcia
Learn more

Val d'Orcia

14 km away • from $92

Siena Historic Center (Siena Centro Storico)
Learn more

Siena Historic Center (Siena Centro Storico)

16 km away • from $26

National Art Gallery of Siena (Pinacoteca Nazionale Siena)
Learn more

National Art Gallery of Siena (Pinacoteca Nazionale Siena)

32 km away • from $1.14

Frequently Asked Questions

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

Among the 38 tour options we compare across booking platforms, prices vary significantly. You can expect to pay between $65 and $1,380, with a typical price range falling between $141 and $349.

There is a diverse mix of experiences available. The largest share of the options we compare are group activities, but 29% are private tours, which may suit those looking for a more personalized experience. We also found a handful of options tagged as eco-friendly.

Based on pooled data from 1,526 reviews across booking platforms, the experiences are highly regarded. They hold an average rating of 4.57★, and the vast majority of sentiment is positive. Reviewers frequently describe the experiences as amazing, wonderful, and a great experience, often highlighting the terrific tour guides and the wide range of wines available.

It is wise to plan ahead. While many options offer instant confirmation, about 13% of the tours we compare are flagged as likely to sell out. Booking early ensures you secure your preferred time slot.

The duration depends on the specific itinerary you choose. Most experiences last between 3.7 and 11 hours, with a median duration of 8 hours.

Yes, there is a good level of variety for international travellers. The options we compare are offered in 8 different languages: English, Italian, Spanish, French, Portuguese, Chinese, German, and Romanian.

Flexibility is common when booking through various platforms. 74% of the options we compare offer free cancellation, providing peace of mind if your travel plans change.

Book tastings in advance via email or websites. Many top Brunello estates require appointments for cellar tours and tastings.

It is difficult. While buses connect towns, a car is essential to reach remote vineyards and scenic countryside locations easily.

Wear comfortable walking shoes. The cobblestone streets are very steep and can be slippery when wet.

Abbey of Sant'Antimo (Abbazia di Sant'Antimo)6.6kmVal d'Orcia13.7kmPienza15.5kmSiena Historic Center (Siena Centro Storico)15.6kmTemple of San Biagio (Tempio di San Biagio)23.5kmSiena Piazza del Mercato31.8kmPubblico Palace (Palazzo Pubblico)31.9kmSiena Civic Museum (Museo Civico di Siena)31.9kmMangia Tower (Torre del Mangia)31.9kmPubblico Palace (Palazzo Pubblico)31.9kmSiena Cathedral Museum (Museo dell’Opera Metropolitana)31.9km
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