Key West Private Charters
Language $Currency
Login / Sign up
Bookings
Bookings
Wallet
$0.00
Wishlists
Wishlists
Rewards Rewards
Gift cards
Profile
Help Center
Language
Log out
Things To Do Things To Do Top 10 Top 10 City Tours City Tours Swamp Tours Swamp Tours Steamboat Natchez Steamboat Natchez Gift Cards Gift Cards Rewards Rewards Groups Groups FAQ FAQ Contact Contact
Start your search
Change your search
Place or activity
Select Dates
You booked this experience
You're departing on
Google Calendar
Apple Calendar
Microsoft Outlook
Make your trip unforgettable

Small-Group Montepulciano and Pienza Day Trip from Siena

338 Reviews 4.90 out of 5 stars Based on 338 reviews collected by Key West Private Charters and TripAdvisor |
Recommended by 98% of reviewers
98% of reviewers gave this experience a rating of 4 or higher.
|
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Siena, Italy
Book online or call us

from $214.19 per person

Lowest Price Guarantee
Montepulciano
Small-Group Montepulciano and Pienza Day Trip from Siena
Crete Senesi
Pienza
Pienza
Don't miss out!
On average, this is booked 22 (0) days in advance.
8 hours (approx.)
Mobile ticket
Offered in: English

Overview

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, enjoy the landscapes and have lunch on a local farm!

Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.

What's Included

  • Lunch Lunch on local farm with wine
  • Alcoholic beverages Alcoholic Beverages
  • Transport by air-conditioned minivan (maximum 8 passengers)
  • Hotel pickup and drop-off
  • Gratuities
See 1 moreSee 2 more

Meeting Location

Meeting point

Piazza San Domenico
1, 53100 Siena SI, Italy

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

What To Expect

Book Online

Our secure website provides real-time availability, and free, no-hassle cancellations up to 24 hours before your tour begins.
Read more

Safe & secure Easy breezy Hassle‑free

Basilica Cateriniana Di S. Domenico (pass by)

Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity. Travel south out of town on one of the most panoramic roads of Tuscany, through the characteristic moonscapes of the Crete Senesi.
Read more

Chiusure

Enjoy brief stops along the Crete Senesi for for photo opportunities before visiting a quaint, non touristic medieval hamlet. Continue along this stunning landscape and reach the UNESCO heritage site of the Val d’Orcia, where you come across some of Tuscany’s most iconic postcard pictures.
Read more

30 minutes Admission Ticket Free

Historic Centre of the City of Pienza

Arrive to the beautiful, utopian renaissance town of Pienza, one of the first towns to be entirely planned out on paper by important architects of the time. These were called upon by Pope Pius II, the humanist pope who wanted to renovate his native town and bring it new splendor.
Read more

1 hour Admission Ticket Free

Il Duomo di Pienza

Spend your leisure time exploring the Romanesque church of Corsignano or the ideal, Renaissance Cathedral and walk along the scenic route overlooking the valleys and hills beyond. Browse the pretty streets of this gem of a town or some of its many shops of local crafts and products.
Read more

15 minutes Admission Ticket Free

Val D'Orcia

Visit a val d'Orcia dairy farm for a wholesome and refreshing lunch based mainly on the fresh ingredients produced on the farm. Here you can learn about the pecorino sheep cheese making processes, visit the farm animals and learn about the lifestyle of the area. Weather permitting, lunch will be served on a panoramic terrace, overlooking the valley below.
Read more

1 hour Admission Ticket Free

Montepulciano

In the afternoon, visit one of the biggest and proudest of the Tuscan hill towns, Montepulciano. This town was first under the dominance of medieval Siena and then became an ally to renaissance Florence: here you can recognize the influences of both Republics in its architecture and art. Located on a steep hill, you can look over the ledge at the the Tuscany - Umbrian border.
Read more

1 hour Admission Ticket Free

Piazza Grande a Montepulciano

Visit the main square, Piazza Grande, and explore one of the many old wineries carved out of the ground below the city, and taste the Vino Nobile that was produced by the many important and noble families that one lived here.After a short walk around town with your guide, enjoy some free time on a second tasting of the Nobile wine or visit the town’s many stores, palaces, churches and streets. As you follow the main road down the hill, imagine how hard the “Bravio delle Botti” town festival must be: a competition between the neighborhoods of the town that race wine barrels from the bottom of the hill, all the way to the top. On some occasions the itinerary might vary a little. In this case, the tour could be slightly modified but will maintain a similar general imprint, of the same duration and with all the same inclusions.
Read more

30 minutes Admission Ticket Free

Show 6 more stops

Additional Info

  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
  • Specialized infant seats are available
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • This tour/activity will have a maximum of 8 travelers

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Small-Group Montepulciano and Pienza Day Trip from Siena?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CET).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-5493MONTEPULCIANO

Traveler Photos

Reviews

4.90
338 reviews

Average 4.90 out of 5 stars based on 338 traveler reviews collected by Key West Private Charters and partner sites such as Cool Destinations and TripAdvisor

5 stars
315
4 stars
17
3 stars
2
2 stars
3
1 star
1
Don't miss out!
On average, this is booked 22 (0) days in advance.
Siena Tours
Attractions
Guides
Calendar
View more

Similar Tours & Activities

Skip the Line: Siena Duomo and City Walking Tour
4.8 (785)

Skip the Line: Siena Duomo and City Walking Tour

Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and...

2 hours Free Cancellation
4.8 (785)
from
$45
PolaTour The 17 Fountains of the Contradas of Siena
5.0 (1)

PolaTour The 17 Fountains of the Contradas of Siena

Our Polaguides will allow you to discover the most hidden, but no less fascinating places than Siena and its districts and instant photography will allow...

1 to 4 hours Free Cancellation
5.0 (1)
from
$70
San Gimignano, Chianti and Montalcino Tour through Tuscan wine
4.8 (9)

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a...

11 hours Free Cancellation
4.8 (9)
from
$158
Private Tour: Siena Walking Tour
5.0 (43)

Private Tour: Siena Walking Tour

Siena, 'the pearl of the Gothic style,' is a charming medieval town in the center of Tuscany. Come and discover the hidden treasures of this medieval...

2 hours Free Cancellation
5.0 (43)
from
$203
Skip the Line: Siena Duomo and City Walking Tour

Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and …More

4.8 (785)

Skip the Line: Siena Duomo and City Walking Tour

4.8 (785)

Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and...

2 hours Free Cancellation
4.8 (785)
from
$45
PolaTour The 17 Fountains of the Contradas of Siena

Our Polaguides will allow you to discover the most hidden, but no less fascinating places than Siena and its districts and instant photography will allow …More

5.0 (1)

PolaTour The 17 Fountains of the Contradas of Siena

5.0 (1)

Our Polaguides will allow you to discover the most hidden, but no less fascinating places than Siena and its districts and instant photography will allow...

1 to 4 hours Free Cancellation
5.0 (1)
from
$70
San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a …More

4.8 (9)

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

4.8 (9)

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a...

11 hours Free Cancellation
4.8 (9)
from
$158
Private Tour: Siena Walking Tour

Siena, 'the pearl of the Gothic style,' is a charming medieval town in the center of Tuscany. Come and discover the hidden treasures of this medieval …More

5.0 (43)

Private Tour: Siena Walking Tour

5.0 (43)

Siena, 'the pearl of the Gothic style,' is a charming medieval town in the center of Tuscany. Come and discover the hidden treasures of this medieval...

2 hours Free Cancellation
5.0 (43)
from
$203

Travelers Who Bought This Tour Also Bought

Skip the Line: Siena Duomo and City Walking Tour
4.8 (785)

Skip the Line: Siena Duomo and City Walking Tour

Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and...

2 hours Free Cancellation
4.8 (785)
from
$45
Siena: Val d’Orcia Wine Tour with Lunch & Brunello
4.1 (94)

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

Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion...

10 to 11 hours Free Cancellation
4.1 (94)
from
$124
Siena Medieval Power Quest: Self-Guided Family Feud Game
4.2 (26)

Siena Medieval Power Quest: Self-Guided Family Feud Game

Unravel the secrets of medieval Siena through a thrilling quest of power, rivalry, and hidden history. This isn’t just a walk - it’s an adventure...

60 to 90 minutes Free Cancellation
4.2 (26)
from
$8
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
4.9 (1,036)

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover...

9 hours Free Cancellation
4.9 (1,036)
from
$214
Skip the Line: Siena Duomo and City Walking Tour

Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and …More

4.8 (785)

Skip the Line: Siena Duomo and City Walking Tour

4.8 (785)

Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and...

2 hours Free Cancellation
4.8 (785)
from
$45
Siena: Val d’Orcia Wine Tour with Lunch & Brunello

Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion …More

4.1 (94)

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

4.1 (94)

Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion...

10 to 11 hours Free Cancellation
4.1 (94)
from
$124
Siena Medieval Power Quest: Self-Guided Family Feud Game

Unravel the secrets of medieval Siena through a thrilling quest of power, rivalry, and hidden history. This isn’t just a walk - it’s an adventure …More

4.2 (26)

Siena Medieval Power Quest: Self-Guided Family Feud Game

4.2 (26)

Unravel the secrets of medieval Siena through a thrilling quest of power, rivalry, and hidden history. This isn’t just a walk - it’s an adventure...

60 to 90 minutes Free Cancellation
4.2 (26)
from
$8
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover …More

4.9 (1,036)

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

4.9 (1,036)

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover...

9 hours Free Cancellation
4.9 (1,036)
from
$214

Frequently Asked Questions (7)

Activity name

The answers provided below were previously given in response to questions from Key West Private Charters customers.

Filter by:

Q: What is the cancellation policy for the Small-Group Montepulciano and Pienza Day Trip from Siena?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CET).
  • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Lunch. Lunch on local farm with wine.
  • Alcoholic beverages. Alcoholic Beverages.
  • Transport by air-conditioned minivan (maximum 8 passengers).
  • Driver/Guide.
The following is NOT included:
  • Hotel pickup and drop-off.
  • Gratuities.
Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Small-Group Montepulciano and Pienza Day Trip from Siena is as follows:

  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Small-Group Montepulciano and Pienza Day Trip from Siena will be included in your confirmation email from Key West Private Charters. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • LunchLunch on local farm with wine
  • Alcoholic beveragesAlcoholic Beverages
  • Transport by air-conditioned minivan (maximum 8 passengers)
  • Driver/Guide
  • Hotel pickup and drop-off
  • Gratuities

Additional Info

Activity name

  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Specialized infant seats are available
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • This tour/activity will have a maximum of 8 travelers

Report Product Issue

Activity name